38:
617:
594:
916:
29:
6673:
1151:, and profound gonadotoxicity. Other side effects may include easy bruising/bleeding, joint pain, mouth sores, slow-healing existing wounds, unusual decrease in the amount of urine or unusual tiredness or weakness. Potential side effects also include leukopenia, infection, bladder toxicity, and cancer.
1563:
Phosphoramide mustard, one of the principal toxic metabolites of cyclophosphamide, was synthesized and reported by
Friedman and Seligman in 1954 ...It was postulated that the presence of the phosphate bond to the nitrogen atom could inactivate the nitrogen mustard moiety, but the phosphate bond would
3705:
Gross R, Wulf G (1959). "Klinische und experimentelle
Erfahrungen mit zyk lischen und nichtzyklischen Phosphamidestern des N-Losl in der Chemotherapie von Tumoren" [Clinical and experimental experiences with metallic cyclical and non-cyclical Phosphamidestern the N-losl in the chemotherapy of
1513:
that does not give rise to the toxic metabolites phosphoramide mustard and acrolein. This is because carboxycyclophosphamide cannot undergo β-elimination (the carboxylate acts as an electron-donating group, nullifying the potential for transformation), preventing nitrogen mustard activation and
1346:(where the cumulative dose is typically less than 20 grams of cyclophosphamide) carries an AML risk of less than 1/2000, with some studies finding no increased risk compared to background. Other treatment regimens involving higher doses may carry risks of 1–2% or higher.
2982:
Radis CD, Kahl LE, Baker GL, Wasko MC, Cash JM, Gallatin A, Stolzer BL, Agarwal AK, Medsger TA, Kwoh CK (August 1995). "Effects of cyclophosphamide on the development of malignancy and on long-term survival of patients with rheumatoid arthritis. A 20-year followup study".
1401:. A small proportion of aldophosphamide freely diffuses into cells, where it is decomposed into two compounds, phosphoramide mustard and acrolein. The active metabolites of cyclophosphamide are highly protein bound and distributed to all tissues, are assumed to cross the
1212:(sodium 2-mercaptoethane sulfonate), a sulfhydryl donor which binds and detoxifies acrolein. Intermittent dosing of cyclophosphamide decreases cumulative drug dose, reduces bladder exposure to acrolein and has equal efficacy to daily treatment in the management of
903:. It is used to quickly control the disease. Due to its toxicity, it is replaced as soon as possible by less toxic drugs. Regular and frequent laboratory evaluations are required to monitor kidney function, avoid drug-induced bladder complications and screen for
1621:
Because of its impact on the immune system, it is used in animal studies. Rodents are injected intraperitoneally with either a single dose of 150 mg/kg or two doses (150 and 100 mg/kg) spread over two days. This can be used for applications such as:
1177:
when compounded by intravenous fluids administered to prevent drug-induced cystitis. While SIADH has been described primarily with higher doses of cyclophosphamide, it can also occur with the lower doses used in the management of inflammatory disorders.
1588:
Oncology). Brock and his team synthesised and screened more than 1,000 candidate oxazaphosphorine compounds. They converted the base nitrogen mustard into a nontoxic "transport form". This transport form was a prodrug, subsequently
1564:
be cleaved in gastric cancers and other tumors which had a high phosphamidase content. However, in studies carried out after the clinical efficacy of cyclophosphamide was demonstrated, phosphoramide mustard proved to be cytotoxic
1630:
may be concerned about potential human pathogenicity of an engineered microbe when conducting an MCAN review. Particularly for bacteria with potential consumer exposure they require testing of the microbe on immuno-compromised
1349:
Cyclophosphamide-induced AML, when it happens, typically presents some years after treatment, with incidence peaking around 3–9 years. After nine years, the risk falls to background. When AML occurs, it is often preceded by a
1415:
Cyclophosphamide metabolites are primarily excreted in the urine unchanged, and drug dosing should be appropriately adjusted in the setting of renal dysfunction. Drugs altering hepatic microsomal enzyme activity (e.g.,
1432:) may result in accelerated metabolism of cyclophosphamide into its active metabolites, increasing both pharmacologic and toxic effects of the drug; alternatively, drugs that inhibit hepatic microsomal enzymes (e.g.
3306:
Donelli MG, Bartosek I, Guaitani A, Martini A, Colombo T, Pacciarini MA, Modica R (April 1976). "Importance of pharmacokinetic studies on cyclophosphamide (NSC-26271) in understanding its cytotoxic effect".
2571:
Salido M, Macarron P, Hernández-García C, D'Cruz DP, Khamashta MA, Hughes GR (2003). "Water intoxication induced by low-dose cyclophosphamide in two patients with systemic lupus erythematosus".
2744:
Pryor BD, Bologna SG, Kahl LE (September 1996). "Risk factors for serious infection during treatment with cyclophosphamide and high-dose corticosteroids for systemic lupus erythematosus".
1597:
converted into the active, toxic form. The first clinical trials were published at the end of the 1950s. In 1959 it became the eighth cytotoxic anticancer agent to be approved by the
3457:
Kohn FR, Sladek NE (October 1985). "Aldehyde dehydrogenase activity as the basis for the relative insensitivity of murine pluripotent hematopoietic stem cells to oxazaphosphorines".
1271:
in males and females, the likelihood of which increases with cumulative drug dose and increasing patient age. Such infertility is usually temporary, but can be permanent. The use of
256:
5659:
2662:
Monach PA, Arnold LM, Merkel PA (January 2010). "Incidence and prevention of bladder toxicity from cyclophosphamide in the treatment of rheumatic diseases: a data-driven review".
6604:
3785:"Neutropenia induced in outbred mice by a simplified low-dose cyclophosphamide regimen: characterization and applicability to diverse experimental models of infectious diseases"
2779:
Suryaprasad A, Stone JH (July 2008). "When is it safe to stop
Pneumocystis jiroveci pneumonia prophylaxis? Insights from three cases complicating autoimmune diseases".
5880:
5870:
2318:
Singh G, Fries JF, Williams CA, Zatarain E, Spitz P, Bloch DA (February 1991). "Toxicity profiles of disease modifying antirheumatic drugs in rheumatoid arthritis".
5515:
3519:
Sistigu A, Viaud S, Chaput N, Bracci L, Proietti E, Zitvogel L (July 2011). "Immunomodulatory effects of cyclophosphamide and implementations for vaccine design".
3422:
Hall AG, Tilby MJ (September 1992). "Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies".
1170:
1547:
of recipient hosts (for donor T cells) has been used to enhance immunity in naïve hosts, and to enhance adoptive T cell immunotherapy regimens, as well as active
5695:
5885:
6733:
3402:
211:
5652:
1275:
in women of reproductive age before administration of intermittently dosed cyclophosphamide may diminish the risks of premature menopause and infertility.
5865:
3492:
Friedman OM, Wodinsky I, Myles A (April 1976). "Cyclophosphamide (NSC-26271)-related phosphoramide mustards- recent advances and historical perspective".
3835:"EPA: Notifications, FY 1998 to Present - Biotechnology Program under the Toxic Substances Control Act (TSCA) | New Chemicals Program | US EPA"
3222:
Giraud B, Hebert G, Deroussent A, Veal GJ, Vassal G, Paci A (August 2010). "Oxazaphosphorines: new therapeutic strategies for an old class of drugs".
6534:
3942:
1471:
The main effect of cyclophosphamide is due to its metabolite phosphoramide mustard. This metabolite is only formed in cells that have low levels of
5645:
2382:"Risk of serious infections with immunosuppressive drugs and glucocorticoids for lupus nephritis: a systematic review and network meta-analysis"
1331:(therapy-related AML, or "t-AML") is thought to occur either by cyclophosphamide-inducing mutations or selecting for a high-risk myeloid clone.
955:, and although concerns about toxicity restrict its use to patients with severe disease, it remains an important treatment for life-threatening
5735:
1651:
5905:
5710:
3377:
Vigouroux D, Voltaire L (1995). "" [Prolonged neuromuscular block induced by mivacurium in a patient treated with cyclophosphamide].
2038:"Comparative effectiveness of immunosuppressive drugs and corticosteroids for lupus nephritis: a systematic review and network meta-analysis"
1627:
135:
6554:
5575:
4642:
719:
6046:
5925:
5805:
4471:
4451:
4436:
3655:
3638:
1085:
D) except for life-threatening circumstances in the mother. Additional relative contraindications to the use of cyclophosphamide include
2295:
2278:
6529:
6226:
6166:
2466:
Malik SW, Myers JL, DeRemee RA, Specks U (December 1996). "Lung toxicity associated with cyclophosphamide use. Two distinct patterns".
3861:"Immunosuppressive effect of cyclophosphamide on white blood cells and lymphocyte subpopulations from peripheral blood of Balb/c mice"
6314:
5920:
5835:
5976:
3766:
3060:
1753:
1124:
1062:
1505:. ALDHs protect these actively proliferating tissues against toxic effects of phosphoramide mustard and acrolein by converting
1444:) result in slower conversion of cyclophosphamide into its metabolites and consequently reduced therapeutic and toxic effects.
1334:
This risk may be dependent on dose and other factors, including the condition, other agents or treatment modalities (including
4858:
3838:
1708:
5603:
3935:
1895:
1491:
888:
3334:
Koseoglu V, Chiang J, Chan KW (December 1999). "Acquired pseudocholinesterase deficiency after high-dose cyclophosphamide".
764:
2863:
Balow JE, Austin HA, Tsokos GC, Antonovych TT, Steinberg AD, Klippel JH (January 1987). "NIH conference. Lupus nephritis".
1539:
Enhanced grafting of adoptively transferred, tumor-reactive effector T cells by the creation of an immunologic space niche.
960:
5225:
3408:
1479:
N-7 positions (known as interstrand and intrastrand crosslinkages, respectively). This is irreversible and leads to cell
2087:
Gertz MA (December 2014). "Immunoglobulin light chain amyloidosis: 2014 update on diagnosis, prognosis, and treatment".
4377:
4333:
4211:
3920:
2699:"Controlled trial of pulse methylprednisolone versus two regimens of pulse cyclophosphamide in severe lupus nephritis"
6698:
4136:
739:
695:
5679:
5620:
3928:
980:
830:
6454:
4652:
2230:"Haploidentical bone marrow and stem cell transplantation: experience with post-transplantation cyclophosphamide"
1354:
phase, before developing into overt acute leukemia. Cyclophosphamide-induced leukemia will often involve complex
1109:
1050:
869:
379:
241:
2536:
Bressler RB, Huston DP (March 1985). "Water intoxication following moderate-dose intravenous cyclophosphamide".
2501:
Floyd JD, Nguyen DT, Lobins RL, Bashir Q, Doll DC, Perry MC (October 2005). "Cardiotoxicity of cancer therapy".
1061:
of the graft. The use of a high dose cyclophosphamide post-transplant in a half matched or haploidentical donor
6728:
6136:
5271:
4273:
4163:
1559:
As reported by O. M. Colvin in his study of the development of cyclophosphamide and its clinical applications,
1208:. Risks of hemorrhagic cystitis can be minimized with adequate fluid intake, avoidance of nighttime dosage and
3726:
5193:
5176:
5051:
4815:
4193:
1002:, cyclophosphamide is used for early phases of treatment and later substituted by other medications, such as
3901:
3562:
Friedman OM, Seligman AM (1954). "Preparation of N-Phosphorylated
Derivatives of Bis-β-chloroethylamine1a".
6718:
6646:
4925:
4521:
1598:
1544:
1324:
1304:
1105:
964:
612:
493:
3080:
2181:"HLA-haploidentical blood or marrow transplantation with high-dose, post-transplantation cyclophosphamide"
6181:
5875:
5668:
5127:
1659:
1300:
573:
4517:
4487:
6703:
6663:
4307:
5956:
5951:
4412:
6713:
5483:
5373:
5363:
3917:
Novel cyclic phosphoric acid ester amides, and the production thereof. (patent for cyclophosphamide).
1861:
1827:
1382:
1264:
1046:
562:
6439:
5986:
5825:
6708:
6564:
6479:
5530:
5066:
4316:
3101:
Huttunen KM, Raunio H, Rautio J (September 2011). "Prodrugs--from serendipity to rational design".
2697:
Boumpas DT, Austin HA, Vaughn EM, Klippel JH, Steinberg AD, Yarboro CH, Balow JE (September 1992).
1437:
1351:
1100:
D drug and causes birth defects. First trimester exposure to cyclophosphamide for the treatment of
589:
3589:
Colvin OM (August 1999). "An overview of cyclophosphamide development and clinical applications".
2619:
Emadi A, Jones RJ, Brodsky RA (November 2009). "Cyclophosphamide and cancer: golden anniversary".
2431:
Twohig KJ, Matthay RA (March 1990). "Pulmonary effects of cytotoxic agents other than bleomycin".
2345:
Lohrmann HP (1984). "The problem of permanent bone marrow damage after cytotoxic drug treatment".
5608:
5348:
5063:
4549:
4397:
4324:
1510:
1398:
1252:
1240:
1128:
904:
193:
125:
6126:
5755:
5428:
5418:
5151:
4993:
1655:
1452:
1394:
1328:
1244:
972:
814:
324:
3267:"Cyclophosphamide pharmacokinetics and dose requirements in patients with renal insufficiency"
1989:"Research and therapeutics-traditional and emerging therapies in systemic lupus erythematosus"
1680:
6693:
4700:
4347:
1448:
1323:
patients within the first decade after receiving cyclophosphamide, compared with one case of
1120:
542:
37:
5971:
5961:
6309:
6281:
6271:
5890:
5098:
4975:
4496:
1585:
1386:
1320:
1312:
1197:
1154:
Pulmonary injury appears rare, but can present with two clinical patterns: an early, acute
1136:
1066:
984:
976:
853:
502:
346:
5966:
1463:
agents can result in delayed bladder emptying and prolonged bladder exposure to acrolein.
482:
8:
6111:
6011:
5935:
5637:
5383:
5283:
5262:
4983:
4805:
4637:
4368:
4264:
1652:"cyclophosphamide – definition of cyclophosphamide in English from the Oxford dictionary"
1634:
Cyclophosphamide provides a positive control when studying immune-response of a new drug.
1232:
887:
Cyclophosphamide was approved for medical use in the United States in 1959. It is on the
408:
204:
200:
6305:
3757:
3727:"Oxazaphosphorine cytostatics: past-present-future. Seventh Cain Memorial Award lecture"
3144:
Boddy AV, Yule SM (April 2000). "Metabolism and pharmacokinetics of oxazaphosphorines".
1749:
616:
593:
417:
145:
6584:
6339:
6140:
5671:
4441:
3950:
3811:
3784:
3544:
3359:
3247:
3169:
3126:
2923:
2845:
2726:
2644:
2596:
2408:
2381:
2254:
2245:
2229:
2205:
2180:
2161:
2112:
2064:
2037:
2013:
1988:
1964:
1939:
1804:
1779:
1339:
1159:
1097:
1082:
988:
956:
900:
865:
861:
826:
167:
3602:
3390:
3200:
2444:
6723:
6289:
5996:
5550:
5139:
3973:
3880:
3816:
3738:
3687:
3660:
3606:
3536:
3501:
3474:
3470:
3439:
3435:
3394:
3351:
3316:
3288:
3283:
3266:
3265:
Haubitz M, Bohnenstengel F, Brunkhorst R, Schwab M, Hofmann U, Busse D (April 2002).
3239:
3204:
3161:
3157:
3118:
3072:
3041:
3000:
2964:
2915:
2911:
2898:
Periti P, Mazzei T, Mini E (2002). "Clinical pharmacokinetics of depot leuprorelin".
2880:
2837:
2796:
2761:
2718:
2714:
2679:
2636:
2588:
2553:
2518:
2483:
2448:
2413:
2362:
2327:
2300:
2259:
2210:
2153:
2104:
2069:
2018:
1969:
1920:
1891:
1809:
1700:
1335:
1003:
952:
876:
family of medications. It is believed to work by interfering with the duplication of
790:
293:
280:
268:
159:
3363:
3173:
3130:
3036:
3019:
2927:
2816:"Frequency, risk factors and prophylaxis of infection in ANCA-associated vasculitis"
2648:
2600:
2116:
1533:
Elimination of T regulatory cells (CD4CD25 T cells) in naive and tumor-bearing hosts
1475:. Phosphoramide mustard forms DNA crosslinks both between and within DNA strands at
6574:
6294:
6176:
5991:
5981:
5895:
5555:
5327:
5042:
4661:
4382:
3872:
3834:
3806:
3796:
3650:
3598:
3571:
3548:
3528:
3466:
3431:
3386:
3343:
3278:
3231:
3196:
3153:
3110:
3031:
2992:
2959:
2954:
2942:
2907:
2872:
2827:
2788:
2753:
2730:
2710:
2671:
2628:
2580:
2545:
2510:
2475:
2440:
2403:
2393:
2354:
2290:
2249:
2241:
2200:
2192:
2165:
2143:
2096:
2059:
2049:
2008:
2000:
1959:
1955:
1951:
1938:
La Mantia L, Milanese C, Mascoli N, D'Amico R, Weinstock-Guttman B (January 2007).
1835:
1799:
1791:
1590:
1577:
1316:
1058:
873:
834:
798:
629:
306:
224:
55:
3783:
Zuluaga AF, Salazar BE, Rodriguez CA, Zapata AX, Agudelo M, Vesga O (March 2006).
3251:
2849:
2004:
1231:
arising secondary to cyclophosphamide usage can predispose people to a variety of
1108:
displays a pattern of anomalies labeled "cyclophosphamide embryopathy", including
6677:
6251:
6146:
6026:
5009:
4971:
4762:
4184:
4099:
3876:
3235:
3061:"Enzymatic basis of cyclophosphamide activation by hepatic microsomes of the rat"
2479:
2277:
Enns GM, Roeder E, Chan RT, Ali-Khan Catts Z, Cox VA, Golabi M (September 1999).
1685:
1522:
1506:
1460:
1456:
1433:
1378:
1213:
1190:
999:
968:
442:
334:
314:
20:
1912:
1795:
1338:), treatment length and intensity. For some regimens, it is rare. For instance,
1123:
from cyclophosphamide are related to the cumulative medication dose and include
130:
Lyophilized
Cytoxan, Endoxan, Cytoxan, Neosar, Procytox, Revimmune, Cycloblastin
6599:
6519:
6389:
6246:
6101:
6066:
5725:
5614:
5163:
4754:
4248:
4112:
3999:
3969:
3956:
2876:
2632:
2549:
2132:"The evolution of T-cell depletion in haploidentical stem-cell transplantation"
1370:
Oral cyclophosphamide is rapidly absorbed and then converted by mixed-function
1308:
1163:
1132:
1031:
971:
may respond to pulsed cyclophosphamide. Cyclophosphamide is also used to treat
806:
3913:
3624:
3532:
2584:
2398:
2054:
1393:, aldophosphamide. Most of the aldophosphamide is then oxidised by the enzyme
6687:
6539:
6414:
6299:
6261:
6156:
6121:
6056:
5855:
5815:
5715:
5458:
4833:
4706:
4587:
4530:
4288:
4237:
2943:"Hematologic malignant neoplasms after drug exposure in rheumatoid arthritis"
1610:
1526:
1343:
1027:
1023:
936:
818:
810:
706:
605:
3691:
3656:
10.1002/(SICI)1097-0142(19960801)78:3<542::AID-CNCR23>3.0.CO;2-Y
2514:
747:
InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
6624:
6594:
6569:
6524:
6469:
6464:
6449:
6444:
6434:
6429:
6354:
6256:
6236:
6221:
6216:
6211:
6196:
6091:
6081:
5910:
5850:
5785:
5780:
5775:
5770:
5750:
5740:
5535:
5499:
5398:
5388:
5342:
5338:
5300:
5208:
4998:
4937:
4933:
4914:
4909:
4888:
4877:
4691:
4685:
4671:
4666:
4597:
4592:
4545:
4431:
4298:
4278:
4207:
4156:
4146:
3960:
3952:
3884:
3820:
3801:
3610:
3540:
3355:
3347:
3292:
3243:
3165:
3122:
3045:
2996:
2968:
2919:
2841:
2800:
2757:
2683:
2640:
2592:
2522:
2417:
2304:
2296:
10.1002/(SICI)1096-8628(19990917)86:3<237::AID-AJMG8>3.0.CO;2-V
2263:
2214:
2157:
2108:
2073:
2022:
1973:
1924:
1913:"Goodpasture Syndrome (Anti-glomerular Basement Membrane Antibody Disease)"
1832:
World Health
Organization model list of essential medicines: 21st list 2019
1813:
1487:
1421:
1355:
1174:
1147:(hair loss) or thinning of hair, changes in color and texture of the hair,
1019:
932:
924:
786:
219:
3742:
3664:
3505:
3478:
3443:
3398:
3320:
3208:
3114:
3076:
3004:
2884:
2765:
2722:
2557:
2487:
2452:
2366:
2331:
1381:
system) in the liver to active metabolites. The main active metabolite is
6609:
6579:
6559:
6509:
6384:
6379:
6364:
6334:
6161:
6116:
6076:
6071:
6021:
6016:
6001:
5840:
5800:
5705:
5580:
5560:
5545:
5540:
5525:
5488:
5463:
5408:
5378:
5322:
5295:
5168:
5109:
5081:
5071:
5024:
4988:
4904:
4866:
4848:
4843:
4823:
4800:
4771:
4749:
4729:
4719:
4570:
4555:
4535:
4421:
4352:
4338:
4293:
4226:
4221:
4198:
4173:
4141:
4084:
4047:
4024:
4009:
4004:
3989:
1548:
1441:
1406:
1296:
1272:
1268:
1228:
1224:
1155:
1112:, ear and facial abnormalities, absence of digits and hypoplastic limbs.
1090:
1078:
1034:. It appears to be an alternative to the more traditional treatment with
1015:
857:
838:
153:
3759:
ISMP's List of Error-Prone
Abbreviations, Symbols, and Dose Designations
3575:
2570:
2279:"Apparent cyclophosphamide (cytoxan) embryopathy: a distinct phenotype?"
2196:
1840:
856:. Other severe side effects include an increased future risk of cancer,
462:
6589:
6549:
6494:
6484:
6424:
6409:
6394:
6374:
6349:
6344:
6324:
6319:
6276:
6266:
6231:
6206:
6186:
6151:
6130:
6086:
6061:
5845:
5810:
5795:
5790:
5759:
5720:
5700:
5570:
5478:
5473:
5453:
5448:
5443:
5438:
5433:
5403:
5393:
5358:
5353:
5333:
5288:
5276:
5251:
5246:
5236:
5218:
5213:
5203:
5198:
5156:
5144:
5132:
5104:
5091:
5086:
5056:
5019:
5014:
4952:
4947:
4893:
4838:
4790:
4776:
4724:
4711:
4680:
4613:
4602:
4575:
4565:
4560:
4506:
4461:
4456:
4357:
4321:
4253:
4243:
4232:
4216:
4168:
4151:
4127:
4079:
4067:
4019:
1609:
The abbreviation CP is common, although abbreviating drug names is not
1581:
1515:
1502:
1425:
1284:
1248:
1193:
995:
845:
671:
473:
2832:
2815:
2792:
2675:
2358:
2148:
2131:
2100:
1263:
Cyclophosphamide has been found to significantly increase the risk of
915:
6514:
6504:
6499:
6489:
6474:
6459:
6404:
6359:
6329:
6191:
6171:
6096:
6036:
6031:
5900:
5830:
5820:
5765:
5585:
5565:
5520:
5510:
5504:
5423:
5368:
5317:
5241:
5231:
5186:
5173:
5114:
5076:
5004:
4942:
4883:
4872:
4828:
4785:
4744:
4738:
4734:
4696:
4623:
4618:
4608:
4580:
4540:
4501:
4476:
4466:
4426:
4072:
4062:
4057:
4052:
4014:
1499:
1480:
1429:
1201:
1086:
1035:
849:
428:
359:
139:
3264:
3187:
Wiernik PH, Duncan JH (May 1971). "Cyclophosphamide in human milk".
2698:
1490:
toxicity as ALDHs are present in relatively large concentrations in
6419:
6399:
6369:
6241:
6201:
6051:
6041:
5915:
5494:
5468:
5413:
5181:
5119:
4899:
4795:
4767:
4446:
4283:
3860:
3755:
1937:
1890:(11th ed.). Philadelphia: Elsevier. 2020. pp. 1007–1091.
1402:
1390:
1292:
1288:
1186:
1148:
1144:
1140:
940:
928:
802:
794:
522:
453:
28:
1166:
is a major problem with people treated with higher dose regimens.
1038:
in people who are ill-suited for autologous stem cell transplant.
694:
6629:
6614:
6544:
6006:
5730:
4402:
4303:
4117:
3978:
1476:
1417:
1412:
It is specifically in the oxazaphosphorine group of medications.
1371:
1255:, but some advocate its use when receiving high-dose medication.
1236:
1205:
822:
16:
Medication used as chemotherapy and to suppress the immune system
2227:
1327:
in 119 rheumatoid arthritis patients with no history. Secondary
1057:
against the person receiving them. GVHD can often be avoided by
4042:
1594:
1536:
Induction of T cell growth factors, such as type I IFNs, and/or
1374:
1101:
1054:
553:
364:
3305:
844:
Most people develop side effects. Common side effects include
3782:
3024:
Hematology. American
Society of Hematology. Education Program
3020:"Etiology and management of therapy-related myeloid leukemia"
1495:
1209:
685:
533:
339:
2276:
2228:
Robinson TM, O'Donnell PV, Fuchs EJ, Luznik L (April 2016).
578:
3859:
Huyan XH, Lin YP, Gao T, Chen RY, Fan YM (September 2011).
3749:
2862:
1862:"Cyclophosphamide: Martindale: The Complete Drug Reference"
1472:
513:
112:
100:
91:
73:
64:
5667:
3221:
2696:
2468:
American
Journal of Respiratory and Critical Care Medicine
2317:
82:
3065:
The
Journal of Pharmacology and Experimental Therapeutics
1826:
881:
877:
399:-bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxide
5680:
3518:
2036:
Singh JA, Hossain A, Kotb A, Wells GA (September 2016).
1844:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
1568:(footnote omitted), but to have a low therapeutic index
1171:
syndrome of inappropriate antidiuretic hormone secretion
2500:
2465:
2380:
Singh JA, Hossain A, Kotb A, Wells G (September 2016).
889:
World Health Organization's List of Essential Medicines
1593:
into cancer cells. Once in the cells, the prodrug was
6661:
3491:
2940:
2813:
2379:
2035:
1752:. The American Society of Health-System Pharmacists.
1169:
High-dose intravenous cyclophosphamide can cause the
94:
88:
85:
79:
67:
61:
58:
3100:
109:
103:
70:
2981:
1551:strategies, inducing objective antitumor immunity.
97:
76:
3333:
3224:Expert Opinion on Drug Metabolism & Toxicology
2941:Bernatsky S, Clarke AE, Suissa S (February 2008).
2661:
1077:Like other alkylating agents, cyclophosphamide is
837:, among other conditions. It is taken by mouth or
3639:"The history of the oxazaphosphorine cytostatics"
3379:Annales Françaises d'Anesthésie et de Réanimation
3376:
2618:
6685:
3686:]. Asta-Forschung und Therapie (in German).
3561:
2897:
2778:
2743:
1200:, which is associated with microscopic or gross
441:
3858:
2814:Kronbichler A, Jayne DR, Mayer G (March 2015).
2807:
2614:
2612:
2610:
1919:. Treasure Island, USA: StatPearls Publishing.
1486:Cyclophosphamide has relatively little typical
963:(DMARDs) have been ineffective. For example,
923:The main use of cyclophosphamide is with other
416:
2535:
2129:
1910:
1584:were developed by Norbert Brock and ASTA (now
994:Because of its potential side effects such as
899:Cyclophosphamide is used to treat cancers and
6734:World Health Organization essential medicines
5653:
3936:
3215:
3186:
2430:
3137:
2607:
1986:
1859:
1041:
5936:
3485:
3450:
3052:
1944:The Cochrane Database of Systematic Reviews
1014:Cyclophosphamide, used in combination with
785:among other names, is a medication used as
298:In general: ℞ (Prescription only)
5987:Allopregnanedione (5α-dihydroprogesterone)
5660:
5646:
3943:
3929:
3456:
2820:European Journal of Clinical Investigation
1744:
1742:
1740:
1738:
1736:
1734:
1732:
1730:
1728:
1726:
615:
592:
481:
3810:
3800:
3756:Institute for Safe Medication Practices,
3704:
3654:
3421:
3282:
3143:
3035:
2958:
2831:
2407:
2397:
2294:
2253:
2204:
2147:
2063:
2053:
2012:
1963:
1940:"Cyclophosphamide for multiple sclerosis"
1839:
1803:
1773:
1771:
1065:reduces GVHD, even after using a reduced
1053:because of the immune reactions of donor
501:
5685:Tooltip Constitutive androstane receptor
3677:
3564:Journal of the American Chemical Society
3058:
2344:
1287:and may increase the risk of developing
1125:chemotherapy-induced nausea and vomiting
914:
825:. As an immune suppressor it is used in
1780:"Updates in ANCA-associated vasculitis"
1777:
1723:
1358:, which carries a worse prognosis than
1081:and contraindicated in pregnant women (
1063:hematopoietic stem cell transplantation
588:
461:
158:
6686:
6440:Pregnanedione (5β-dihydroprogesterone)
5826:Pregnanedione (5β-dihydroprogesterone)
3588:
3017:
1820:
1768:
1604:
1466:
1459:. Tricyclic antidepressants and other
1303:of the bladder or other malignancies.
953:decreases the immune system's response
946:
793:. As chemotherapy it is used to treat
606:
274:
5641:
3924:
3724:
3636:
2178:
2086:
1834:. Geneva: World Health Organization.
1451:activity and may result in prolonged
961:disease-modifying antirheumatic drugs
561:
541:
287:
144:
3908:. U.S. National Library of Medicine.
2283:American Journal of Medical Genetics
1860:Brayfield, A, ed. (9 January 2017).
1855:
1853:
1851:
1521:Cyclophosphamide induces beneficial
1455:when administered concurrently with
1072:
223:
4212:ribonucleotide reductase inhibitors
2130:Or-Geva N, Reisner Y (March 2016).
1987:Davis LS, Reimold AM (April 2017).
1756:from the original on 2 January 2017
1181:
521:
432:
13:
4378:Ribonucleotide reductase inhibitor
4334:Ribonucleotide reductase inhibitor
2246:10.1053/j.seminhematol.2016.01.005
1868:. London, UK: Pharmaceutical Press
1711:from the original on 25 April 2015
664:
14:
6745:
4137:Dihydrofolate reductase inhibitor
3894:
3603:10.2174/1381612805666230110214512
2621:Nature Reviews. Clinical Oncology
1888:Brenner & Rector's The Kidney
1848:
1576:Cyclophosphamide and the related
1009:
250:
178:
6671:
3865:International Immunopharmacology
3772:from the original on 2011-10-27.
3684:Chemotherapy of malignant tumors
3284:10.1046/j.1523-1755.2002.00279.x
3158:10.2165/00003088-200038040-00001
3059:Cohen JL, Jao JY (August 1970).
2912:10.2165/00003088-200241070-00003
1784:European Journal of Rheumatology
1529:. Suggested mechanisms include:
1447:Cyclophosphamide reduces plasma
1243:. No published guidelines cover
1173:(SIADH) and a potentially fatal
981:granulomatosis with polyangiitis
831:granulomatosis with polyangiitis
652:
646:
640:
54:
36:
27:
3852:
3841:from the original on 2015-06-21
3827:
3776:
3718:
3698:
3671:
3630:
3617:
3582:
3555:
3512:
3415:
3370:
3327:
3299:
3258:
3180:
3094:
3037:10.1182/asheducation-2007.1.453
3011:
2975:
2934:
2891:
2856:
2772:
2737:
2690:
2655:
2564:
2529:
2494:
2459:
2424:
2373:
2338:
2311:
2270:
2221:
2172:
2123:
2080:
2029:
1980:
1931:
1911:DeVrieze BW, Hurley JA (2019).
1405:and are known to be present in
1365:
1143:, darkening of the skin/nails,
1115:
1051:allogeneic stem cell transplant
894:
752:Key:CMSMOCZEIVJLDB-UHFFFAOYSA-N
5992:Allopregnanolone (brexanolone)
4274:Thymidylate synthase inhibitor
4164:Thymidylate synthase inhibitor
3680:Chemotherapie maligner Tumoren
2960:10.1001/archinternmed.2007.107
2136:British Journal of Haematology
2089:American Journal of Hematology
1956:10.1002/14651858.CD002819.pub2
1904:
1880:
1693:
1686:Merriam-Webster.com Dictionary
1673:
1644:
1258:
1049:(GVHD) is a major barrier for
1026:has documented efficacy as an
848:, loss of appetite, vomiting,
658:
634:
263:
1:
6647:Receptor/signaling modulators
6605:Tropanyl 3,5-dimethulbenzoate
6455:Pregnenolone 16α-carbonitrile
4194:Adenosine deaminase inhibitor
4035:Block microtubule disassembly
3591:Current Pharmaceutical Design
3391:10.1016/S0750-7658(05)80493-9
3201:10.1016/s0140-6736(71)92474-3
2947:Archives of Internal Medicine
2538:Archives of Internal Medicine
2445:10.1016/S0272-5231(21)00670-5
1638:
868:. Cyclophosphamide is in the
3877:10.1016/j.intimp.2011.04.011
3471:10.1016/0006-2952(85)90719-1
3436:10.1016/0268-960X(92)90028-O
3236:10.1517/17425255.2010.487861
2715:10.1016/0140-6736(92)92292-n
2503:Journal of Clinical Oncology
2480:10.1164/ajrccm.154.6.8970380
1778:Pagnoux C (September 2016).
1325:chronic lymphocytic leukemia
1305:Myeloproliferative neoplasms
1247:prophylaxis for people with
1219:
965:systemic lupus erythematosus
7:
6182:Dodecylbenzenesulfonic acid
5941:Tooltip Pregnane X receptor
5669:Xenobiotic-sensing receptor
3521:Seminars in Immunopathology
3336:Bone Marrow Transplantation
2865:Annals of Internal Medicine
2320:The Journal of Rheumatology
2185:Bone Marrow Transplantation
2005:10.1093/rheumatology/kew417
1796:10.5152/eurjrheum.2015.0043
1616:
1301:transitional cell carcinoma
1278:
1158:and a chronic, progressive
927:agents in the treatment of
846:low white blood cell counts
10:
6750:
2877:10.7326/0003-4819-106-1-79
2633:10.1038/nrclinonc.2009.146
2550:10.1001/archinte.145.3.548
1580:–derived alkylating agent
1554:
919:A Cyclophosphamide IV drip
791:suppress the immune system
624:Chemical and physical data
6638:
5934:
5678:
5598:
5484:Omacetaxine mepesuccinate
5374:Ciltacabtagene autoleucel
5364:Brexucabtagene autoleucel
5310:
5261:
5041:
5034:
4970:
4924:
4857:
4814:
4651:
4636:
4516:
4486:
4411:
4396:
4367:
4263:
4183:
4126:
4109:
4098:
4034:
3987:
3968:
3533:10.1007/s00281-011-0245-0
3146:Clinical Pharmacokinetics
2900:Clinical Pharmacokinetics
2585:10.1191/0961203303lu421cr
2433:Clinics in Chest Medicine
2399:10.1186/s12916-016-0673-8
2055:10.1186/s13643-016-0328-z
1828:World Health Organization
1705:National Cancer Institute
1438:tricyclic antidepressants
1383:4-hydroxycyclophosphamide
1047:Graft-versus-host disease
1042:Graft-versus-host disease
910:
854:bleeding from the bladder
760:
735:
715:
705:
683:
670:
628:
623:
604:
572:
552:
532:
512:
492:
472:
452:
427:
407:
375:
370:
358:
345:
333:
323:
313:
305:
240:
235:
210:
192:
166:
152:
134:
124:
49:
44:
35:
26:
6699:IARC Group 1 carcinogens
6565:Testosterone isocaproate
6480:Reverse triiodothyronine
5531:Talimogene laherparepvec
4398:Topoisomerase inhibitors
4317:DNA polymerase inhibitor
3725:Brock N (January 1989).
3494:Cancer Treatment Reports
3459:Biochemical Pharmacology
3309:Cancer Treatment Reports
2985:Arthritis and Rheumatism
2781:Arthritis and Rheumatism
2746:Arthritis and Rheumatism
2664:Arthritis and Rheumatism
1352:myelodysplastic syndrome
1249:rheumatological diseases
1241:opportunistic infections
205:by injection into a vein
5957:17α-Hydroxyprogesterone
5952:17α-Hydroxypregnenolone
5349:Axicabtagene ciloleucel
3953:chemotherapeutic agents
3906:Drug Information Portal
3789:BMC Infectious Diseases
3637:Brock N (August 1996).
3103:Pharmacological Reviews
2515:10.1200/JCO.2005.08.789
1543:Thus, cyclophosphamide
1511:carboxycyclophosphamide
1399:carboxycyclophosphamide
1319:, occurred in 5 of 119
1253:immunosuppressive drugs
1129:bone marrow suppression
943:and some solid tumors.
727:O=P1(OCCCN1)N(CCCl)CCCl
5516:Sitimagene ceradenovec
5429:Idecabtagene vicleucel
4994:Methyl aminolevulinate
3802:10.1186/1471-2334-6-55
3348:10.1038/sj.bmt.1702097
2997:10.1002/art.1780380815
2758:10.1002/art.1780390906
2234:Seminars in Hematology
2179:Fuchs EJ (June 2015).
1999:(suppl_1): i100–i113.
1656:OxfordDictionaries.com
1574:
1492:bone marrow stem cells
1453:neuromuscular blockade
1395:aldehyde dehydrogenase
1329:acute myeloid leukemia
1121:Adverse drug reactions
1096:Cyclophosphamide is a
973:minimal change disease
920:
815:small cell lung cancer
711:2 °C (36 °F)
6729:Chloroethyl compounds
5696:6,7-Dimethylesculetin
5005:Porphyrin derivatives
4701:Melphalan flufenamide
4348:Hypomethylating agent
3957:antineoplastic agents
3914:U.S. patent 3,018,302
3625:U.S. patent 3,018,302
3115:10.1124/pr.110.003459
1701:"NCI Drug Dictionary"
1561:
1093:or bladder toxicity.
918:
839:injection into a vein
6283:Hypericum perforatum
6272:Hetacillin potassium
5334:Asparagine depleters
5263:Receptor antagonists
5177:+abiraterone acetate
3271:Kidney International
1591:actively transported
1525:effects in adaptive
1449:pseudocholinesterase
1321:rheumatoid arthritis
1313:non-Hodgkin lymphoma
1283:Cyclophosphamide is
1198:hemorrhagic cystitis
1137:hemorrhagic cystitis
1089:, active infection,
1067:conditioning regimen
985:Goodpasture syndrome
977:rheumatoid arthritis
905:bone marrow toxicity
880:and the creation of
6719:Phosphorodiamidates
6112:Cyproterone acetate
6012:Amlodipine besylate
5384:Denileukin diftitox
5284:Retinoid X receptor
4984:Aminolevulinic acid
4806:Triethylenemelamine
4638:Crosslinking of DNA
4369:Deoxyribonucleotide
4308:+gimeracil/oteracil
3678:Wilmanns H (1958).
3576:10.1021/ja01632a006
2197:10.1038/bmt.2015.92
1707:. 2 February 2011.
1605:Society and culture
1467:Mechanism of action
1265:premature menopause
1028:off-label treatment
957:autoimmune diseases
947:Autoimmune diseases
901:autoimmune diseases
283:(Prescription only)
259:(Prescription only)
23:
6585:Thonzonium bromide
6340:Methylprednisolone
6141:prasterone sulfate
5625:Never to phase III
4442:Etirinotecan pegol
3902:"Cyclophosphamide"
3018:Larson RA (2007).
2474:(6 Pt 1): 1851–6.
2191:(Suppl 2): S31–6.
2042:Systematic Reviews
1750:"Cyclophosphamide"
1689:. Merriam-Webster.
1681:"cyclophosphamide"
1662:on August 25, 2012
1385:, which exists in
1267:in females and of
1110:growth restriction
1098:pregnancy category
1083:pregnancy category
989:multiple sclerosis
921:
866:pulmonary fibrosis
862:allergic reactions
827:nephrotic syndrome
319:>75% (by mouth)
19:
6704:Nitrogen mustards
6656:
6655:
6290:Indinavir sulfate
5997:Alpha-Lipoic acid
5972:Δ-Androstenedione
5962:Δ-Androstenedione
5635:
5634:
5594:
5593:
5551:Tigilanol tiglate
5043:Enzyme inhibitors
4966:
4965:
4962:
4961:
4662:Nitrogen mustards
4632:
4631:
4392:
4391:
4094:
4093:
2833:10.1111/eci.12410
2793:10.1002/art.23822
2676:10.1002/art.25061
2359:10.1159/000225819
2149:10.1111/bjh.13868
2101:10.1002/ajh.23828
1897:978-0-323-53265-5
1866:MedicinesComplete
1204:and occasionally
1073:Contraindications
1004:mycophenolic acid
951:Cyclophosphamide
781:), also known as
772:
771:
696:Interactive image
574:CompTox Dashboard
291:
278:
266:
254:
182:
6741:
6714:Oxazaphosphinans
6676:
6675:
6674:
6667:
6575:Thiamylal sodium
6310:γ-linolenic acid
6306:α-Linolenic acid
6304:Linolenic acid:
6295:Lasalocid sodium
6285:(St John's wort)
6177:Docusate calcium
6107:Cyclophosphamide
5982:Allopregnanediol
5967:Δ-Androstenediol
5942:
5938:
5896:Ethinylestradiol
5746:Cyclophosphamide
5686:
5682:
5662:
5655:
5648:
5639:
5638:
5556:Tisagenlecleucel
5328:Arsenic trioxide
5039:
5038:
4972:Photosensitizers
4763:Alkyl sulfonates
4677:Cyclophosphamide
4649:
4648:
4588:Anthracenediones
4409:
4408:
4383:Hydroxycarbamide
4124:
4123:
4107:
4106:
3985:
3984:
3945:
3938:
3931:
3922:
3921:
3916:
3909:
3889:
3888:
3856:
3850:
3849:
3847:
3846:
3831:
3825:
3824:
3814:
3804:
3780:
3774:
3773:
3771:
3764:
3753:
3747:
3746:
3722:
3716:
3715:
3708:Strahlentherapie
3702:
3696:
3695:
3675:
3669:
3668:
3658:
3634:
3628:
3627:
3621:
3615:
3614:
3586:
3580:
3579:
3559:
3553:
3552:
3516:
3510:
3509:
3489:
3483:
3482:
3454:
3448:
3447:
3419:
3413:
3412:
3407:
3374:
3368:
3367:
3331:
3325:
3324:
3303:
3297:
3296:
3286:
3262:
3256:
3255:
3219:
3213:
3212:
3184:
3178:
3177:
3141:
3135:
3134:
3098:
3092:
3091:
3089:
3088:
3079:. Archived from
3056:
3050:
3049:
3039:
3015:
3009:
3008:
2979:
2973:
2972:
2962:
2938:
2932:
2931:
2895:
2889:
2888:
2860:
2854:
2853:
2835:
2811:
2805:
2804:
2776:
2770:
2769:
2741:
2735:
2734:
2694:
2688:
2687:
2659:
2653:
2652:
2616:
2605:
2604:
2568:
2562:
2561:
2533:
2527:
2526:
2498:
2492:
2491:
2463:
2457:
2456:
2428:
2422:
2421:
2411:
2401:
2377:
2371:
2370:
2342:
2336:
2335:
2315:
2309:
2308:
2298:
2274:
2268:
2267:
2257:
2225:
2219:
2218:
2208:
2176:
2170:
2169:
2151:
2127:
2121:
2120:
2084:
2078:
2077:
2067:
2057:
2033:
2027:
2026:
2016:
1984:
1978:
1977:
1967:
1935:
1929:
1928:
1908:
1902:
1901:
1884:
1878:
1877:
1875:
1873:
1857:
1846:
1845:
1843:
1824:
1818:
1817:
1807:
1775:
1766:
1765:
1763:
1761:
1746:
1721:
1720:
1718:
1716:
1697:
1691:
1690:
1677:
1671:
1670:
1668:
1667:
1658:. Archived from
1648:
1578:nitrogen mustard
1523:immunomodulatory
1317:multiple myeloma
1196:and can lead to
1189:is toxic to the
1182:Bladder bleeding
1059:T-cell depletion
931:, some forms of
874:nitrogen mustard
870:alkylating agent
835:organ transplant
833:, and following
799:multiple myeloma
775:Cyclophosphamide
768:
767:
698:
678:
666:
660:
654:
648:
642:
636:
619:
608:
597:
596:
582:
580:
565:
545:
525:
505:
485:
465:
445:
435:
434:
420:
350:
289:
286:
276:
273:
265:
262:
252:
249:
227:
180:
177:
162:
148:
119:
118:
115:
114:
111:
106:
105:
102:
99:
96:
93:
90:
87:
84:
81:
78:
75:
72:
69:
66:
63:
60:
40:
31:
24:
22:
21:Cyclophosphamide
18:
6749:
6748:
6744:
6743:
6742:
6740:
6739:
6738:
6709:Organochlorides
6684:
6683:
6682:
6672:
6670:
6662:
6659:
6657:
6652:
6634:
6535:Suberoylanilide
6252:Fluorometholone
6147:Dibunate sodium
6027:Aurothioglucose
5940:
5930:
5866:3,17β-Estradiol
5684:
5674:
5666:
5636:
5631:
5630:
5615:Clinical trials
5590:
5311:Other/ungrouped
5306:
5257:
5030:
5010:Porfimer sodium
4958:
4920:
4853:
4810:
4640:
4628:
4512:
4482:
4400:
4388:
4363:
4259:
4179:
4115:
4113:antimetabolites
4111:
4110:DNA precursors/
4102:
4100:DNA replication
4090:
4030:
4000:Vinca alkaloids
3976:
3964:
3949:
3912:
3900:
3897:
3892:
3857:
3853:
3844:
3842:
3833:
3832:
3828:
3781:
3777:
3769:
3762:
3754:
3750:
3731:Cancer Research
3723:
3719:
3703:
3699:
3676:
3672:
3635:
3631:
3623:
3622:
3618:
3587:
3583:
3560:
3556:
3517:
3513:
3490:
3486:
3465:(19): 3465–71.
3455:
3451:
3420:
3416:
3405:
3375:
3371:
3332:
3328:
3304:
3300:
3277:(4): 1495–501.
3263:
3259:
3220:
3216:
3185:
3181:
3142:
3138:
3099:
3095:
3086:
3084:
3057:
3053:
3016:
3012:
2980:
2976:
2939:
2935:
2896:
2892:
2861:
2857:
2812:
2808:
2777:
2773:
2742:
2738:
2709:(8822): 741–5.
2695:
2691:
2660:
2656:
2617:
2608:
2569:
2565:
2534:
2530:
2509:(30): 7685–96.
2499:
2495:
2464:
2460:
2429:
2425:
2378:
2374:
2343:
2339:
2316:
2312:
2275:
2271:
2226:
2222:
2177:
2173:
2128:
2124:
2095:(12): 1132–40.
2085:
2081:
2034:
2030:
1985:
1981:
1950:(1): CD002819.
1936:
1932:
1909:
1905:
1898:
1886:
1885:
1881:
1871:
1869:
1858:
1849:
1825:
1821:
1776:
1769:
1759:
1757:
1748:
1747:
1724:
1714:
1712:
1699:
1698:
1694:
1679:
1678:
1674:
1665:
1663:
1650:
1649:
1645:
1641:
1619:
1607:
1557:
1545:preconditioning
1507:aldophosphamide
1469:
1461:anticholinergic
1457:succinylcholine
1434:corticosteroids
1397:(ALDH) to make
1379:cytochrome P450
1368:
1281:
1261:
1222:
1214:lupus nephritis
1184:
1118:
1075:
1044:
1012:
1000:ovarian failure
969:lupus nephritis
949:
913:
897:
763:
761:
756:
753:
748:
743:
742:
731:
728:
723:
722:
701:
676:
663:
657:
651:
645:
639:
600:
576:
568:
548:
528:
508:
488:
468:
448:
431:
423:
403:
400:
383:
382:
348:
325:Protein binding
315:Bioavailability
307:Pharmacokinetic
301:
231:
195:
188:
169:
108:
57:
53:
17:
12:
11:
5:
6747:
6737:
6736:
6731:
6726:
6721:
6716:
6711:
6706:
6701:
6696:
6681:
6680:
6654:
6653:
6651:
6650:
6643:
6639:
6636:
6635:
6633:
6632:
6627:
6618:
6617:
6612:
6607:
6602:
6600:Troleandomycin
6597:
6592:
6587:
6582:
6577:
6572:
6567:
6562:
6557:
6552:
6547:
6542:
6537:
6532:
6527:
6522:
6520:Spironolactone
6517:
6512:
6507:
6502:
6497:
6492:
6487:
6482:
6477:
6472:
6467:
6462:
6457:
6452:
6447:
6442:
6437:
6432:
6427:
6422:
6417:
6412:
6407:
6402:
6397:
6392:
6390:Norelgestromin
6387:
6382:
6377:
6372:
6367:
6362:
6357:
6352:
6347:
6342:
6337:
6332:
6327:
6322:
6317:
6312:
6302:
6297:
6292:
6287:
6279:
6274:
6269:
6264:
6259:
6254:
6249:
6247:Flucloxacillin
6244:
6239:
6234:
6229:
6224:
6219:
6214:
6209:
6204:
6199:
6194:
6189:
6184:
6179:
6174:
6169:
6164:
6159:
6154:
6149:
6144:
6134:
6124:
6119:
6114:
6109:
6104:
6102:Corticosterone
6099:
6094:
6089:
6084:
6079:
6074:
6069:
6067:Chlorpromazine
6064:
6059:
6054:
6049:
6044:
6039:
6034:
6029:
6024:
6019:
6014:
6009:
6004:
5999:
5994:
5989:
5984:
5979:
5974:
5969:
5964:
5959:
5954:
5945:
5943:
5932:
5931:
5929:
5928:
5923:
5918:
5913:
5908:
5903:
5898:
5893:
5888:
5886:17-Androstanol
5883:
5881:3β-Androstanol
5878:
5876:3α-Androstenol
5873:
5871:3α-Androstanol
5868:
5859:
5858:
5853:
5848:
5843:
5838:
5833:
5828:
5823:
5818:
5813:
5808:
5803:
5798:
5793:
5788:
5783:
5778:
5773:
5768:
5763:
5753:
5748:
5743:
5738:
5733:
5728:
5726:Chlorpromazine
5723:
5718:
5713:
5708:
5703:
5698:
5689:
5687:
5676:
5675:
5665:
5664:
5657:
5650:
5642:
5633:
5632:
5629:
5628:
5627:
5626:
5623:
5612:
5606:
5600:
5599:
5596:
5595:
5592:
5591:
5589:
5588:
5583:
5578:
5573:
5568:
5563:
5558:
5553:
5548:
5543:
5538:
5533:
5528:
5523:
5518:
5513:
5508:
5502:
5491:
5486:
5481:
5476:
5471:
5466:
5461:
5456:
5451:
5446:
5441:
5436:
5431:
5426:
5421:
5416:
5411:
5406:
5401:
5396:
5391:
5386:
5381:
5376:
5371:
5366:
5361:
5356:
5351:
5346:
5330:
5325:
5320:
5314:
5312:
5308:
5307:
5305:
5304:
5292:
5280:
5267:
5265:
5259:
5258:
5256:
5255:
5249:
5244:
5239:
5234:
5222:
5216:
5211:
5206:
5201:
5190:
5184:
5179:
5171:
5164:PARP inhibitor
5160:
5148:
5136:
5124:
5123:
5122:
5117:
5112:
5107:
5095:
5089:
5084:
5079:
5074:
5060:
5047:
5045:
5036:
5032:
5031:
5029:
5028:
5022:
5017:
5012:
5001:
4996:
4991:
4986:
4980:
4978:
4968:
4967:
4964:
4963:
4960:
4959:
4957:
4956:
4950:
4945:
4940:
4930:
4928:
4922:
4921:
4919:
4918:
4912:
4907:
4896:
4891:
4886:
4881:
4869:
4863:
4861:
4855:
4854:
4852:
4851:
4846:
4841:
4836:
4831:
4826:
4820:
4818:
4816:Platinum-based
4812:
4811:
4809:
4808:
4803:
4798:
4793:
4781:
4780:
4774:
4758:
4757:
4752:
4747:
4742:
4732:
4727:
4715:
4714:
4709:
4704:
4694:
4689:
4683:
4674:
4669:
4657:
4655:
4646:
4634:
4633:
4630:
4629:
4627:
4626:
4621:
4616:
4611:
4606:
4600:
4595:
4584:
4578:
4573:
4568:
4563:
4558:
4553:
4543:
4538:
4531:Anthracyclines
4526:
4524:
4514:
4513:
4511:
4510:
4504:
4492:
4490:
4484:
4483:
4481:
4480:
4474:
4469:
4464:
4459:
4454:
4449:
4444:
4439:
4434:
4429:
4417:
4415:
4406:
4394:
4393:
4390:
4389:
4387:
4386:
4373:
4371:
4365:
4364:
4362:
4361:
4355:
4343:
4342:
4329:
4328:
4312:
4311:
4301:
4296:
4291:
4286:
4281:
4269:
4267:
4261:
4260:
4258:
4257:
4251:
4249:Mercaptopurine
4240:
4235:
4230:
4224:
4219:
4203:
4202:
4189:
4187:
4181:
4180:
4178:
4177:
4171:
4160:
4154:
4149:
4144:
4132:
4130:
4121:
4104:
4096:
4095:
4092:
4091:
4089:
4088:
4076:
4070:
4065:
4060:
4055:
4050:
4038:
4036:
4032:
4031:
4029:
4028:
4022:
4017:
4012:
4007:
3995:
3993:
3982:
3966:
3965:
3951:Intracellular
3948:
3947:
3940:
3933:
3925:
3919:
3918:
3910:
3896:
3895:External links
3893:
3891:
3890:
3851:
3826:
3775:
3748:
3717:
3697:
3670:
3629:
3616:
3581:
3554:
3511:
3484:
3449:
3414:
3369:
3342:(12): 1367–8.
3326:
3315:(4): 395–401.
3298:
3257:
3230:(8): 919–938.
3214:
3179:
3152:(4): 291–304.
3136:
3093:
3051:
3010:
2974:
2933:
2906:(7): 485–504.
2890:
2855:
2806:
2771:
2752:(9): 1475–82.
2736:
2689:
2654:
2627:(11): 638–47.
2606:
2563:
2528:
2493:
2458:
2423:
2372:
2337:
2310:
2269:
2220:
2171:
2122:
2079:
2028:
1979:
1930:
1903:
1896:
1879:
1847:
1819:
1790:(3): 122–133.
1767:
1722:
1692:
1672:
1642:
1640:
1637:
1636:
1635:
1632:
1618:
1615:
1606:
1603:
1556:
1553:
1541:
1540:
1537:
1534:
1468:
1465:
1367:
1364:
1309:acute leukemia
1280:
1277:
1260:
1257:
1221:
1218:
1183:
1180:
1164:Cardiotoxicity
1117:
1114:
1074:
1071:
1043:
1040:
1032:AL amyloidosis
1011:
1010:AL amyloidosis
1008:
948:
945:
912:
909:
896:
893:
807:ovarian cancer
770:
769:
758:
757:
755:
754:
751:
749:
746:
738:
737:
736:
733:
732:
730:
729:
726:
718:
717:
716:
713:
712:
709:
703:
702:
700:
699:
691:
689:
681:
680:
674:
668:
667:
661:
655:
649:
643:
637:
632:
626:
625:
621:
620:
610:
602:
601:
599:
598:
585:
583:
570:
569:
567:
566:
558:
556:
550:
549:
547:
546:
538:
536:
530:
529:
527:
526:
518:
516:
510:
509:
507:
506:
498:
496:
490:
489:
487:
486:
478:
476:
470:
469:
467:
466:
458:
456:
450:
449:
447:
446:
438:
436:
425:
424:
422:
421:
413:
411:
405:
404:
402:
401:
386:
378:
377:
376:
373:
372:
368:
367:
362:
356:
355:
352:
343:
342:
337:
331:
330:
327:
321:
320:
317:
311:
310:
303:
302:
300:
299:
296:
284:
271:
260:
246:
244:
238:
237:
233:
232:
230:
229:
216:
214:
208:
207:
198:
196:administration
190:
189:
187:
186:
184:
174:
172:
164:
163:
156:
150:
149:
142:
132:
131:
128:
122:
121:
51:
47:
46:
42:
41:
33:
32:
15:
9:
6:
4:
3:
2:
6746:
6735:
6732:
6730:
6727:
6725:
6722:
6720:
6717:
6715:
6712:
6710:
6707:
6705:
6702:
6700:
6697:
6695:
6692:
6691:
6689:
6679:
6669:
6668:
6665:
6660:
6649:
6648:
6644:
6641:
6640:
6637:
6631:
6628:
6626:
6623:
6620:
6619:
6616:
6613:
6611:
6608:
6606:
6603:
6601:
6598:
6596:
6593:
6591:
6588:
6586:
6583:
6581:
6578:
6576:
6573:
6571:
6568:
6566:
6563:
6561:
6558:
6556:
6553:
6551:
6548:
6546:
6543:
6541:
6540:Sulfisoxazole
6538:
6536:
6533:
6531:
6528:
6526:
6523:
6521:
6518:
6516:
6513:
6511:
6508:
6506:
6503:
6501:
6498:
6496:
6493:
6491:
6488:
6486:
6483:
6481:
6478:
6476:
6473:
6471:
6468:
6466:
6463:
6461:
6458:
6456:
6453:
6451:
6448:
6446:
6443:
6441:
6438:
6436:
6433:
6431:
6428:
6426:
6423:
6421:
6418:
6416:
6415:Phenobarbital
6413:
6411:
6408:
6406:
6403:
6401:
6398:
6396:
6393:
6391:
6388:
6386:
6383:
6381:
6378:
6376:
6373:
6371:
6368:
6366:
6363:
6361:
6358:
6356:
6353:
6351:
6348:
6346:
6343:
6341:
6338:
6336:
6333:
6331:
6328:
6326:
6323:
6321:
6318:
6316:
6313:
6311:
6307:
6303:
6301:
6300:Levothyroxine
6298:
6296:
6293:
6291:
6288:
6286:
6284:
6280:
6278:
6275:
6273:
6270:
6268:
6265:
6263:
6262:Guggulsterone
6260:
6258:
6255:
6253:
6250:
6248:
6245:
6243:
6240:
6238:
6235:
6233:
6230:
6228:
6225:
6223:
6220:
6218:
6215:
6213:
6210:
6208:
6205:
6203:
6200:
6198:
6195:
6193:
6190:
6188:
6185:
6183:
6180:
6178:
6175:
6173:
6170:
6168:
6165:
6163:
6160:
6158:
6157:Dicloxacillin
6155:
6153:
6150:
6148:
6145:
6142:
6138:
6135:
6132:
6128:
6125:
6123:
6122:Dexamethasone
6120:
6118:
6115:
6113:
6110:
6108:
6105:
6103:
6100:
6098:
6095:
6093:
6090:
6088:
6085:
6083:
6080:
6078:
6075:
6073:
6070:
6068:
6065:
6063:
6060:
6058:
6057:Cephaloridine
6055:
6053:
6050:
6048:
6045:
6043:
6040:
6038:
6035:
6033:
6030:
6028:
6025:
6023:
6020:
6018:
6015:
6013:
6010:
6008:
6005:
6003:
6000:
5998:
5995:
5993:
5990:
5988:
5985:
5983:
5980:
5978:
5975:
5973:
5970:
5968:
5965:
5963:
5960:
5958:
5955:
5953:
5950:
5947:
5946:
5944:
5939:
5933:
5927:
5924:
5922:
5919:
5917:
5914:
5912:
5909:
5907:
5904:
5902:
5899:
5897:
5894:
5892:
5889:
5887:
5884:
5882:
5879:
5877:
5874:
5872:
5869:
5867:
5864:
5861:
5860:
5857:
5856:Valproic acid
5854:
5852:
5849:
5847:
5844:
5842:
5839:
5837:
5834:
5832:
5829:
5827:
5824:
5822:
5819:
5817:
5816:Phenobarbital
5814:
5812:
5809:
5807:
5804:
5802:
5799:
5797:
5794:
5792:
5789:
5787:
5784:
5782:
5779:
5777:
5774:
5772:
5769:
5767:
5764:
5761:
5757:
5754:
5752:
5749:
5747:
5744:
5742:
5739:
5737:
5734:
5732:
5729:
5727:
5724:
5722:
5719:
5717:
5716:Carbamazepine
5714:
5712:
5709:
5707:
5704:
5702:
5699:
5697:
5694:
5691:
5690:
5688:
5683:
5677:
5673:
5670:
5663:
5658:
5656:
5651:
5649:
5644:
5643:
5640:
5624:
5622:
5619:
5618:
5616:
5613:
5610:
5607:
5605:
5602:
5601:
5597:
5587:
5584:
5582:
5579:
5577:
5574:
5572:
5569:
5567:
5564:
5562:
5559:
5557:
5554:
5552:
5549:
5547:
5544:
5542:
5539:
5537:
5534:
5532:
5529:
5527:
5524:
5522:
5519:
5517:
5514:
5512:
5509:
5506:
5503:
5501:
5497:
5496:
5492:
5490:
5487:
5485:
5482:
5480:
5477:
5475:
5472:
5470:
5467:
5465:
5462:
5460:
5459:Lurbinectedin
5457:
5455:
5452:
5450:
5447:
5445:
5442:
5440:
5437:
5435:
5432:
5430:
5427:
5425:
5422:
5420:
5417:
5415:
5412:
5410:
5407:
5405:
5402:
5400:
5397:
5395:
5392:
5390:
5387:
5385:
5382:
5380:
5377:
5375:
5372:
5370:
5367:
5365:
5362:
5360:
5357:
5355:
5352:
5350:
5347:
5344:
5340:
5336:
5335:
5331:
5329:
5326:
5324:
5321:
5319:
5316:
5315:
5313:
5309:
5302:
5298:
5297:
5293:
5290:
5286:
5285:
5281:
5278:
5274:
5273:
5269:
5268:
5266:
5264:
5260:
5253:
5250:
5248:
5245:
5243:
5240:
5238:
5235:
5233:
5229:
5227:
5223:
5220:
5217:
5215:
5212:
5210:
5207:
5205:
5202:
5200:
5196:
5195:
5191:
5188:
5185:
5183:
5180:
5178:
5175:
5172:
5170:
5166:
5165:
5161:
5158:
5154:
5153:
5149:
5146:
5142:
5141:
5137:
5134:
5130:
5129:
5125:
5121:
5118:
5116:
5113:
5111:
5108:
5106:
5103:
5102:
5101:
5100:
5096:
5093:
5090:
5088:
5085:
5083:
5080:
5078:
5075:
5073:
5069:
5068:
5065:
5061:
5058:
5054:
5053:
5049:
5048:
5046:
5044:
5040:
5037:
5033:
5026:
5023:
5021:
5018:
5016:
5013:
5011:
5007:
5006:
5002:
5000:
4997:
4995:
4992:
4990:
4987:
4985:
4982:
4981:
4979:
4977:
4973:
4969:
4954:
4951:
4949:
4946:
4944:
4941:
4939:
4935:
4932:
4931:
4929:
4927:
4926:Intercalation
4923:
4916:
4913:
4911:
4908:
4906:
4902:
4901:
4897:
4895:
4892:
4890:
4887:
4885:
4882:
4879:
4875:
4874:
4870:
4868:
4865:
4864:
4862:
4860:
4856:
4850:
4847:
4845:
4842:
4840:
4837:
4835:
4834:Dicycloplatin
4832:
4830:
4827:
4825:
4822:
4821:
4819:
4817:
4813:
4807:
4804:
4802:
4799:
4797:
4794:
4792:
4789:
4787:
4783:
4782:
4778:
4775:
4773:
4769:
4766:
4764:
4760:
4759:
4756:
4753:
4751:
4748:
4746:
4743:
4740:
4736:
4733:
4731:
4728:
4726:
4723:
4721:
4717:
4716:
4713:
4710:
4708:
4707:Prednimustine
4705:
4702:
4698:
4695:
4693:
4690:
4687:
4684:
4682:
4678:
4675:
4673:
4670:
4668:
4665:
4663:
4659:
4658:
4656:
4654:
4650:
4647:
4644:
4639:
4635:
4625:
4622:
4620:
4617:
4615:
4612:
4610:
4607:
4604:
4601:
4599:
4596:
4594:
4590:
4589:
4585:
4582:
4579:
4577:
4574:
4572:
4569:
4567:
4564:
4562:
4559:
4557:
4554:
4551:
4547:
4544:
4542:
4539:
4537:
4533:
4532:
4528:
4527:
4525:
4523:
4522:Intercalation
4519:
4515:
4508:
4505:
4503:
4499:
4498:
4494:
4493:
4491:
4489:
4485:
4478:
4475:
4473:
4470:
4468:
4465:
4463:
4460:
4458:
4455:
4453:
4450:
4448:
4445:
4443:
4440:
4438:
4435:
4433:
4430:
4428:
4424:
4423:
4419:
4418:
4416:
4414:
4410:
4407:
4404:
4399:
4395:
4384:
4380:
4379:
4375:
4374:
4372:
4370:
4366:
4359:
4356:
4354:
4350:
4349:
4345:
4344:
4340:
4336:
4335:
4331:
4330:
4326:
4325:+daunorubicin
4323:
4319:
4318:
4314:
4313:
4309:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4289:Doxifluridine
4287:
4285:
4282:
4280:
4276:
4275:
4271:
4270:
4268:
4266:
4262:
4255:
4252:
4250:
4246:
4245:
4241:
4239:
4238:Rabacfosadine
4236:
4234:
4231:
4228:
4225:
4223:
4220:
4218:
4214:
4213:
4209:
4205:
4204:
4200:
4196:
4195:
4191:
4190:
4188:
4186:
4182:
4175:
4172:
4170:
4166:
4165:
4161:
4158:
4155:
4153:
4150:
4148:
4145:
4143:
4139:
4138:
4134:
4133:
4131:
4129:
4125:
4122:
4119:
4114:
4108:
4105:
4101:
4097:
4086:
4082:
4081:
4077:
4074:
4071:
4069:
4066:
4064:
4061:
4059:
4056:
4054:
4051:
4049:
4045:
4044:
4040:
4039:
4037:
4033:
4026:
4023:
4021:
4018:
4016:
4013:
4011:
4008:
4006:
4002:
4001:
3997:
3996:
3994:
3991:
3986:
3983:
3980:
3975:
3971:
3967:
3962:
3958:
3954:
3946:
3941:
3939:
3934:
3932:
3927:
3926:
3923:
3915:
3911:
3907:
3903:
3899:
3898:
3886:
3882:
3878:
3874:
3871:(9): 1293–7.
3870:
3866:
3862:
3855:
3840:
3836:
3830:
3822:
3818:
3813:
3808:
3803:
3798:
3794:
3790:
3786:
3779:
3768:
3761:
3760:
3752:
3744:
3740:
3736:
3732:
3728:
3721:
3713:
3710:(in German).
3709:
3706:tumors].
3701:
3693:
3689:
3685:
3681:
3674:
3666:
3662:
3657:
3652:
3648:
3644:
3640:
3633:
3626:
3620:
3612:
3608:
3604:
3600:
3597:(8): 555–60.
3596:
3592:
3585:
3577:
3573:
3569:
3565:
3558:
3550:
3546:
3542:
3538:
3534:
3530:
3527:(4): 369–83.
3526:
3522:
3515:
3507:
3503:
3500:(4): 337–46.
3499:
3495:
3488:
3480:
3476:
3472:
3468:
3464:
3460:
3453:
3445:
3441:
3437:
3433:
3430:(3): 163–73.
3429:
3425:
3424:Blood Reviews
3418:
3410:
3404:
3400:
3396:
3392:
3388:
3385:(6): 508–10.
3384:
3381:(in French).
3380:
3373:
3365:
3361:
3357:
3353:
3349:
3345:
3341:
3337:
3330:
3322:
3318:
3314:
3310:
3302:
3294:
3290:
3285:
3280:
3276:
3272:
3268:
3261:
3253:
3249:
3245:
3241:
3237:
3233:
3229:
3225:
3218:
3210:
3206:
3202:
3198:
3195:(7705): 912.
3194:
3190:
3183:
3175:
3171:
3167:
3163:
3159:
3155:
3151:
3147:
3140:
3132:
3128:
3124:
3120:
3116:
3112:
3109:(3): 750–71.
3108:
3104:
3097:
3083:on 2021-08-28
3082:
3078:
3074:
3071:(2): 206–10.
3070:
3066:
3062:
3055:
3047:
3043:
3038:
3033:
3029:
3025:
3021:
3014:
3006:
3002:
2998:
2994:
2991:(8): 1120–7.
2990:
2986:
2978:
2970:
2966:
2961:
2956:
2953:(4): 378–81.
2952:
2948:
2944:
2937:
2929:
2925:
2921:
2917:
2913:
2909:
2905:
2901:
2894:
2886:
2882:
2878:
2874:
2870:
2866:
2859:
2851:
2847:
2843:
2839:
2834:
2829:
2826:(3): 346–68.
2825:
2821:
2817:
2810:
2802:
2798:
2794:
2790:
2787:(7): 1034–9.
2786:
2782:
2775:
2767:
2763:
2759:
2755:
2751:
2747:
2740:
2732:
2728:
2724:
2720:
2716:
2712:
2708:
2704:
2700:
2693:
2685:
2681:
2677:
2673:
2669:
2665:
2658:
2650:
2646:
2642:
2638:
2634:
2630:
2626:
2622:
2615:
2613:
2611:
2602:
2598:
2594:
2590:
2586:
2582:
2578:
2574:
2567:
2559:
2555:
2551:
2547:
2543:
2539:
2532:
2524:
2520:
2516:
2512:
2508:
2504:
2497:
2489:
2485:
2481:
2477:
2473:
2469:
2462:
2454:
2450:
2446:
2442:
2438:
2434:
2427:
2419:
2415:
2410:
2405:
2400:
2395:
2391:
2387:
2383:
2376:
2368:
2364:
2360:
2356:
2352:
2348:
2341:
2333:
2329:
2326:(2): 188–94.
2325:
2321:
2314:
2306:
2302:
2297:
2292:
2289:(3): 237–41.
2288:
2284:
2280:
2273:
2265:
2261:
2256:
2251:
2247:
2243:
2239:
2235:
2231:
2224:
2216:
2212:
2207:
2202:
2198:
2194:
2190:
2186:
2182:
2175:
2167:
2163:
2159:
2155:
2150:
2145:
2142:(5): 667–84.
2141:
2137:
2133:
2126:
2118:
2114:
2110:
2106:
2102:
2098:
2094:
2090:
2083:
2075:
2071:
2066:
2061:
2056:
2051:
2047:
2043:
2039:
2032:
2024:
2020:
2015:
2010:
2006:
2002:
1998:
1994:
1990:
1983:
1975:
1971:
1966:
1961:
1957:
1953:
1949:
1945:
1941:
1934:
1926:
1922:
1918:
1914:
1907:
1899:
1893:
1889:
1883:
1867:
1863:
1856:
1854:
1852:
1842:
1837:
1833:
1829:
1823:
1815:
1811:
1806:
1801:
1797:
1793:
1789:
1785:
1781:
1774:
1772:
1755:
1751:
1745:
1743:
1741:
1739:
1737:
1735:
1733:
1731:
1729:
1727:
1710:
1706:
1702:
1696:
1688:
1687:
1682:
1676:
1661:
1657:
1653:
1647:
1643:
1633:
1629:
1625:
1624:
1623:
1614:
1613:in medicine.
1612:
1611:best practice
1602:
1600:
1596:
1595:enzymatically
1592:
1587:
1583:
1579:
1573:
1571:
1567:
1560:
1552:
1550:
1546:
1538:
1535:
1532:
1531:
1530:
1528:
1527:immunotherapy
1524:
1519:
1517:
1512:
1508:
1504:
1501:
1497:
1493:
1489:
1484:
1482:
1478:
1474:
1464:
1462:
1458:
1454:
1450:
1445:
1443:
1439:
1435:
1431:
1427:
1423:
1419:
1413:
1410:
1408:
1404:
1400:
1396:
1392:
1388:
1384:
1380:
1376:
1373:
1363:
1361:
1357:
1353:
1347:
1345:
1344:breast cancer
1341:
1337:
1332:
1330:
1326:
1322:
1318:
1314:
1310:
1306:
1302:
1298:
1294:
1290:
1286:
1276:
1274:
1270:
1266:
1256:
1254:
1250:
1246:
1242:
1238:
1234:
1230:
1226:
1217:
1215:
1211:
1207:
1203:
1199:
1195:
1192:
1188:
1179:
1176:
1172:
1167:
1165:
1161:
1157:
1152:
1150:
1146:
1142:
1138:
1134:
1130:
1126:
1122:
1113:
1111:
1107:
1103:
1099:
1094:
1092:
1088:
1084:
1080:
1070:
1068:
1064:
1060:
1056:
1052:
1048:
1039:
1037:
1033:
1029:
1025:
1024:dexamethasone
1021:
1017:
1007:
1005:
1001:
997:
992:
990:
986:
982:
978:
974:
970:
966:
962:
958:
954:
944:
942:
938:
937:neuroblastoma
934:
930:
926:
917:
908:
906:
902:
892:
890:
885:
883:
879:
875:
871:
867:
863:
859:
855:
851:
847:
842:
840:
836:
832:
828:
824:
820:
819:neuroblastoma
816:
812:
811:breast cancer
808:
804:
800:
796:
792:
788:
784:
783:cytophosphane
780:
776:
766:
759:
750:
745:
744:
741:
734:
725:
724:
721:
714:
710:
708:
707:Melting point
704:
697:
693:
692:
690:
687:
682:
675:
673:
669:
633:
631:
627:
622:
618:
614:
611:
609:
607:ECHA InfoCard
603:
595:
591:
590:DTXSID5020364
587:
586:
584:
575:
571:
564:
560:
559:
557:
555:
551:
544:
540:
539:
537:
535:
531:
524:
520:
519:
517:
515:
511:
504:
500:
499:
497:
495:
491:
484:
480:
479:
477:
475:
471:
464:
460:
459:
457:
455:
451:
444:
440:
439:
437:
430:
426:
419:
415:
414:
412:
410:
406:
398:
394:
390:
385:
384:
381:
374:
369:
366:
363:
361:
357:
353:
351:
344:
341:
338:
336:
332:
328:
326:
322:
318:
316:
312:
308:
304:
297:
295:
285:
282:
272:
270:
261:
258:
248:
247:
245:
243:
239:
234:
226:
221:
218:
217:
215:
213:
209:
206:
202:
199:
197:
191:
185:
176:
175:
173:
171:
165:
161:
157:
155:
151:
147:
143:
141:
137:
133:
129:
127:
123:
117:
52:
50:Pronunciation
48:
45:Clinical data
43:
39:
34:
30:
25:
6694:Hepatotoxins
6658:
6645:
6625:Ketoconazole
6622:Antagonists:
6621:
6595:Troglitazone
6570:Tetracycline
6525:Spiroxatrine
6470:Quingestrone
6465:Progesterone
6450:Pregnenolone
6445:Pregnanolone
6435:Pregnanediol
6430:Prednisolone
6355:Mifepristone
6282:
6257:Griseofulvin
6237:Fenbendazole
6222:Famprofazone
6217:Erythromycin
6212:Epothilone B
6197:Eburnamonine
6106:
6092:Clotrimazole
6082:Clofenvinfos
6017:Antimycotics
5948:
5911:Okadaic acid
5863:Antagonists:
5862:
5851:Troglitazone
5786:Mifepristone
5781:Methoxychlor
5776:Griseofulvin
5771:Ellagic acid
5751:Cypermethrin
5745:
5741:Clotrimazole
5692:
5536:Tazemetostat
5500:Alitretinoin
5493:
5419:Estramustine
5399:Elsamitrucin
5389:Eflornithine
5343:Pegaspargase
5339:Asparaginase
5332:
5301:Testolactone
5294:
5282:
5270:
5224:
5209:Panobinostat
5192:
5162:
5150:
5138:
5126:
5097:
5062:
5050:
5003:
4999:Padeliporfin
4938:Dactinomycin
4934:Streptomyces
4915:Temozolomide
4910:Mitozolomide
4898:
4889:Mitobronitol
4878:Procarbazine
4871:
4859:Nonclassical
4784:
4761:
4755:Streptozocin
4720:Nitrosoureas
4718:
4692:Chlorambucil
4686:Trofosfamide
4676:
4672:Chlormethine
4667:Bendamustine
4660:
4598:Mitoxantrone
4593:Losoxantrone
4586:
4546:Daunorubicin
4529:
4495:
4432:Camptothecin
4420:
4376:
4346:
4332:
4315:
4299:Fluorouracil
4279:Capecitabine
4272:
4242:
4206:
4192:
4162:
4157:Pralatrexate
4147:Methotrexate
4135:
4078:
4041:
3998:
3905:
3868:
3864:
3854:
3843:. Retrieved
3829:
3792:
3788:
3778:
3758:
3751:
3734:
3730:
3720:
3711:
3707:
3700:
3683:
3679:
3673:
3649:(3): 542–7.
3646:
3642:
3632:
3619:
3594:
3590:
3584:
3570:(3): 655–8.
3567:
3563:
3557:
3524:
3520:
3514:
3497:
3493:
3487:
3462:
3458:
3452:
3427:
3423:
3417:
3382:
3378:
3372:
3339:
3335:
3329:
3312:
3308:
3301:
3274:
3270:
3260:
3227:
3223:
3217:
3192:
3188:
3182:
3149:
3145:
3139:
3106:
3102:
3096:
3085:. Retrieved
3081:the original
3068:
3064:
3054:
3027:
3023:
3013:
2988:
2984:
2977:
2950:
2946:
2936:
2903:
2899:
2893:
2871:(1): 79–94.
2868:
2864:
2858:
2823:
2819:
2809:
2784:
2780:
2774:
2749:
2745:
2739:
2706:
2702:
2692:
2667:
2663:
2657:
2624:
2620:
2579:(8): 636–9.
2576:
2572:
2566:
2544:(3): 548–9.
2541:
2537:
2531:
2506:
2502:
2496:
2471:
2467:
2461:
2439:(1): 31–54.
2436:
2432:
2426:
2389:
2386:BMC Medicine
2385:
2375:
2353:(3): 180–4.
2350:
2346:
2340:
2323:
2319:
2313:
2286:
2282:
2272:
2237:
2233:
2223:
2188:
2184:
2174:
2139:
2135:
2125:
2092:
2088:
2082:
2045:
2041:
2031:
1996:
1993:Rheumatology
1992:
1982:
1947:
1943:
1933:
1916:
1906:
1887:
1882:
1870:. Retrieved
1865:
1841:10665/325771
1831:
1822:
1787:
1783:
1758:. Retrieved
1713:. Retrieved
1704:
1695:
1684:
1675:
1664:. Retrieved
1660:the original
1646:
1620:
1608:
1575:
1569:
1565:
1562:
1558:
1542:
1520:
1488:chemotherapy
1485:
1470:
1446:
1422:barbiturates
1414:
1411:
1369:
1366:Pharmacology
1359:
1356:cytogenetics
1348:
1336:radiotherapy
1333:
1307:, including
1285:carcinogenic
1282:
1262:
1223:
1185:
1175:hyponatremia
1168:
1153:
1133:stomach ache
1119:
1116:Side effects
1095:
1076:
1045:
1020:lenalidomide
1013:
993:
967:with severe
950:
933:brain cancer
925:chemotherapy
922:
898:
895:Medical uses
886:
843:
787:chemotherapy
782:
778:
774:
773:
762:
396:
392:
388:
347:Elimination
242:Legal status
236:Legal status
6610:Zafirlukast
6580:Thiothixene
6560:Terconazole
6510:Simvastatin
6385:Nisoldipine
6380:Nilvadipine
6365:Nicardipine
6335:Metacycline
6162:Dimercaprol
6117:Demecolcine
6077:Clindamycin
6072:Ciglitazone
6022:Artemisinin
6002:Ambrisentan
5906:Nigramide J
5841:Telmisartan
5801:Nicardipine
5711:Benfuracarb
5706:Artemisinin
5611:from market
5581:Vorasidenib
5561:Trabectedin
5546:Tiazofurine
5541:Tebentafusp
5526:Tagraxofusp
5489:Plitidepsin
5464:Mitoguazone
5409:Epacadostat
5379:Demecolcine
5323:Aflibercept
5296:Sex steroid
5169:Fuzuloparib
5110:Carfilzomib
5082:Palbociclib
5072:Abemaciclib
5025:Verteporfin
4989:Efaproxiral
4905:Dacarbazine
4867:Altretamine
4849:Satraplatin
4844:Oxaliplatin
4824:Carboplatin
4801:Triaziquone
4772:Mannosulfan
4750:Ranimustine
4730:Fotemustine
4571:Pirarubicin
4556:Doxorubicin
4550:+cytarabine
4536:Aclarubicin
4497:Podophyllum
4422:Camptotheca
4353:Azacitidine
4339:Gemcitabine
4294:Floxuridine
4227:Fludarabine
4222:Clofarabine
4208:Halogenated
4199:Pentostatin
4174:Raltitrexed
4142:Aminopterin
4085:Ixabepilone
4080:Epothilones
4048:Cabazitaxel
4025:Vinorelbine
4010:Vincristine
4005:Vinblastine
3990:microtubule
2670:(1): 9–21.
2240:(2): 90–7.
1715:20 December
1549:vaccination
1514:subsequent
1442:allopurinol
1407:breast milk
1387:equilibrium
1340:CMF-therapy
1297:skin cancer
1273:leuprorelin
1269:infertility
1259:Infertility
1229:lymphopenia
1225:Neutropenia
1156:pneumonitis
1091:neutropenia
1079:teratogenic
1016:thalidomide
858:infertility
679: g·mol
613:100.000.015
371:Identifiers
154:MedlinePlus
126:Trade names
6688:Categories
6590:Tianeptine
6555:Tenylidone
6550:Tacrolimus
6495:Rimexolone
6485:Rifampicin
6425:Plicamycin
6410:Paclitaxel
6395:Omeprazole
6375:Nifedipine
6350:Mevastatin
6345:Metyrapone
6325:Lovastatin
6320:Loratadine
6277:Hyperforin
6267:Haloprogin
6232:Felodipine
6207:Enzacamene
6187:Dronabinol
6152:Diclazuril
6131:prasterone
6087:Chloroxine
6062:Cephradine
6032:Bile acids
5846:Tolnaftate
5811:Permethrin
5796:Nevirapine
5791:Nefazodone
5760:prasterone
5721:Carvedilol
5701:Amiodarone
5672:modulators
5576:Verdinexor
5571:Venetoclax
5479:Oblimersen
5474:Navitoclax
5454:Lucanthone
5449:Lonidamine
5444:Lifileucel
5439:Ivosidenib
5434:Imetelstat
5404:Enasidenib
5394:Elesclomol
5359:Bexarotene
5354:Belzutifan
5289:Bexarotene
5277:Atrasentan
5252:Umbralisib
5247:Idelalisib
5237:Copanlisib
5219:Vorinostat
5214:Romidepsin
5204:Entinostat
5199:Belinostat
5157:Masoprocol
5145:Tiazofurin
5133:Anagrelide
5105:Bortezomib
5092:Seliciclib
5087:Ribociclib
5067:inhibitors
5057:Tipifarnib
5020:Temoporfin
5015:Talaporfin
4953:Plicamycin
4948:Mitomycins
4894:Pipobroman
4873:Hydrazines
4839:Nedaplatin
4791:Carboquone
4786:Aziridines
4777:Treosulfan
4725:Carmustine
4712:Uramustine
4681:Ifosfamide
4653:Alkylating
4614:Bisantrene
4603:Pixantrone
4576:Valrubicin
4566:Idarubicin
4561:Epirubicin
4507:Teniposide
4462:Lurtotecan
4457:Irinotecan
4358:Decitabine
4322:Cytarabine
4265:Pyrimidine
4254:Tioguanine
4244:Thiopurine
4233:Nelarabine
4217:Cladribine
4169:Pemetrexed
4152:Pemetrexed
4128:Folic acid
4068:Paclitaxel
4020:Vinflunine
3845:2015-07-01
3737:(1): 1–7.
3087:2014-05-02
2822:(Review).
2392:(1): 137.
2048:(1): 155.
1917:StatPearls
1760:8 December
1666:2016-01-20
1639:References
1582:ifosfamide
1516:alkylation
1503:epithelium
1500:intestinal
1426:rifampicin
1251:receiving
1194:epithelium
996:amenorrhea
684:3D model (
672:Molar mass
543:CHEBI:4027
503:6UXW23996M
474:ChemSpider
409:CAS Number
380:IUPAC name
354:3–12 hours
335:Metabolism
6515:Sirolimus
6505:Ritonavir
6500:Riodipine
6490:Rifaximin
6475:Reserpine
6460:Proadifen
6405:Oxatomide
6360:Nafcillin
6330:Meclizine
6192:Droxidopa
6172:Docetaxel
6097:Colforsin
6047:Bumecaine
6037:Bithionol
5949:Agonists:
5926:T-0901317
5901:Meclizine
5831:Reserpine
5821:Phenytoin
5806:Octicizer
5766:Efavirenz
5693:Agonists:
5621:Phase III
5609:Withdrawn
5586:Vosaroxin
5566:Veliparib
5521:Sotorasib
5511:Selinexor
5505:Tretinoin
5495:Retinoids
5424:Glasdegib
5369:Celecoxib
5318:Adagrasib
5242:Duvelisib
5232:Alpelisib
5187:Rucaparib
5174:Niraparib
5115:Oprozomib
5077:Alvocidib
4943:Bleomycin
4900:Triazenes
4884:Etoglucid
4829:Cisplatin
4745:Nimustine
4739:Semustine
4735:Lomustine
4697:Melphalan
4624:Menogaril
4619:Crisnatol
4609:Amsacrine
4581:Zorubicin
4541:Amrubicin
4502:Etoposide
4477:Topotecan
4472:Silatecan
4467:Rubitecan
4452:Gimatecan
4437:Cositecan
4427:Belotecan
4103:inhibitor
4073:Tesetaxel
4063:Ortataxel
4058:Larotaxel
4053:Docetaxel
4015:Vindesine
3795:(1): 55.
3030:: 453–9.
1872:12 August
1481:apoptosis
1430:phenytoin
1389:with its
1289:lymphomas
1233:bacterial
1220:Infection
1202:hematuria
1087:lactation
1036:melphalan
975:, severe
929:lymphomas
850:hair loss
360:Excretion
349:half-life
194:Routes of
168:Pregnancy
146:Monograph
140:Drugs.com
6724:Prodrugs
6678:Medicine
6642:See also
6530:SR-12813
6420:Piperine
6400:Orlistat
6370:Nicotine
6242:Fentanyl
6227:Febantel
6202:Ecopipam
6167:Dinaline
6052:Cafestol
6042:Bosentan
5916:PK-11195
5469:Mitotane
5414:Eribulin
5182:Olaparib
5120:Ixazomib
4796:Thiotepa
4768:Busulfan
4447:Exatecan
4284:Carmofur
3992:assembly
3955: /
3885:21530682
3839:Archived
3821:16545113
3767:archived
3714:: 361–7.
3692:73296245
3611:10469891
3541:21611872
3364:22946564
3356:10627651
3293:11918757
3244:20446865
3174:39787288
3166:10803453
3131:25381232
3123:21737530
3046:18024664
2969:18299492
2928:10873321
2920:12083977
2842:25627555
2801:18576286
2684:20039416
2649:18219134
2641:19786984
2601:26125211
2593:12945725
2523:16234530
2418:27623861
2347:Oncology
2305:10482872
2264:27000732
2215:26039204
2158:26684279
2117:85480421
2109:25407896
2074:27619512
2023:28375452
1974:17253481
1925:29083697
1830:(2019).
1814:27733943
1754:Archived
1709:Archived
1617:Research
1566:in vitro
1403:placenta
1391:tautomer
1293:leukemia
1187:Acrolein
1160:fibrosis
1149:lethargy
1145:alopecia
1141:diarrhea
1006:or ACA.
941:leukemia
803:leukemia
795:lymphoma
765:(verify)
563:ChEMBL88
454:DrugBank
212:ATC code
201:By mouth
170:category
6630:Sesamin
6615:Zeranol
6545:Suramin
6315:LOE-908
6007:AMI-193
5921:S-07662
5836:TCPOBOP
5731:Chrysin
4403:S phase
4304:Tegafur
4118:S phase
4043:Taxanes
3979:M phase
3812:1434751
3743:2491747
3665:8697402
3549:3360104
3506:1277209
3479:2996550
3444:1422285
3409:2947795
3399:8745976
3321:1277213
3209:4102054
3077:4393764
3005:7639809
2885:3789582
2766:8814058
2731:8800101
2723:1356175
2558:3977522
2488:8970380
2453:1691069
2409:5022202
2367:6374556
2332:1673721
2255:4806368
2206:4634886
2166:1093277
2065:5020478
2014:5850311
1965:8078225
1805:5058451
1570:in vivo
1555:History
1477:guanine
1418:alcohol
1375:enzymes
1372:oxidase
1360:de novo
1206:dysuria
1191:bladder
823:sarcoma
789:and to
630:Formula
463:DB00531
429:PubChem
418:50-18-0
329:>60%
267::
228:)
222: (
220:L01AA01
183: D
160:a682080
6664:Portal
6137:DHEA-S
5977:AA-861
5604:WHO-EM
5228:(Pi3K)
4185:Purine
3988:Block
3883:
3819:
3809:
3741:
3690:
3663:
3643:Cancer
3609:
3547:
3539:
3504:
3477:
3442:
3406:
3397:
3362:
3354:
3319:
3291:
3252:695545
3250:
3242:
3207:
3189:Lancet
3172:
3164:
3129:
3121:
3075:
3044:
3003:
2967:
2926:
2918:
2883:
2850:870510
2848:
2840:
2799:
2764:
2729:
2721:
2703:Lancet
2682:
2647:
2639:
2599:
2591:
2556:
2521:
2486:
2451:
2416:
2406:
2365:
2330:
2303:
2262:
2252:
2213:
2203:
2164:
2156:
2115:
2107:
2072:
2062:
2021:
2011:
1972:
1962:
1923:
1894:
1812:
1802:
1586:Baxter
1279:Cancer
1237:fungal
1102:cancer
1055:T cell
959:where
911:Cancer
864:, and
852:, and
821:, and
720:SMILES
677:261.08
554:ChEMBL
523:D07760
365:Kidney
294:℞-only
292:
279:
269:℞-only
255:
120:
5736:CITCO
5140:IMPDI
5035:Other
3770:(PDF)
3763:(PDF)
3682:[
3545:S2CID
3403:INIST
3360:S2CID
3248:S2CID
3170:S2CID
3127:S2CID
2924:S2CID
2846:S2CID
2727:S2CID
2645:S2CID
2597:S2CID
2573:Lupus
2162:S2CID
2113:S2CID
1631:rats.
1496:liver
1440:, or
1428:, or
1362:AML.
1210:mesna
1106:lupus
740:InChI
686:JSmol
534:ChEBI
340:Liver
6308:and
6127:DHEA
5891:AITC
5756:DHEA
5226:PIKI
5194:HDAC
4643:CCNS
3881:PMID
3817:PMID
3739:PMID
3688:OCLC
3661:PMID
3607:PMID
3537:PMID
3502:PMID
3475:PMID
3440:PMID
3395:PMID
3352:PMID
3317:PMID
3289:PMID
3240:PMID
3205:PMID
3162:PMID
3119:PMID
3073:PMID
3042:PMID
3028:2007
3001:PMID
2965:PMID
2916:PMID
2881:PMID
2838:PMID
2797:PMID
2762:PMID
2719:PMID
2680:PMID
2637:PMID
2589:PMID
2554:PMID
2519:PMID
2484:PMID
2449:PMID
2414:PMID
2363:PMID
2328:PMID
2301:PMID
2260:PMID
2211:PMID
2154:PMID
2105:PMID
2070:PMID
2019:PMID
1970:PMID
1948:2007
1921:PMID
1892:ISBN
1874:2017
1810:PMID
1762:2016
1717:2016
1626:The
1498:and
1473:ALDH
1342:for
1315:and
1239:and
1022:and
987:and
872:and
514:KEGG
494:UNII
483:2804
443:2907
309:data
136:AHFS
5937:PXR
5681:CAR
5272:ERA
5128:PhI
5099:PrI
5064:CDK
4976:PDT
3974:MIs
3970:SPs
3961:L01
3873:doi
3807:PMC
3797:doi
3651:doi
3599:doi
3572:doi
3529:doi
3467:doi
3432:doi
3387:doi
3344:doi
3279:doi
3232:doi
3197:doi
3154:doi
3111:doi
3069:174
3032:doi
2993:doi
2955:doi
2951:168
2908:doi
2873:doi
2869:106
2828:doi
2789:doi
2754:doi
2711:doi
2707:340
2672:doi
2629:doi
2581:doi
2546:doi
2542:145
2511:doi
2476:doi
2472:154
2441:doi
2404:PMC
2394:doi
2355:doi
2291:doi
2250:PMC
2242:doi
2201:PMC
2193:doi
2144:doi
2140:172
2097:doi
2060:PMC
2050:doi
2009:PMC
2001:doi
1960:PMC
1952:doi
1836:hdl
1800:PMC
1792:doi
1628:EPA
1599:FDA
1509:to
1245:PCP
1227:or
1104:or
1030:of
1018:or
998:or
882:RNA
878:DNA
579:EPA
433:CID
281:POM
225:WHO
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5617::
5152:LI
5052:FI
4518:II
4488:II
4310:))
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