473:
450:
857:
38:
29:
3167:
879:
Nitrogen mustards arose from the derivatization of sulphur mustard gas after military personnel exposed to it during World War I were observed to have decreased white blood cell counts. Since the sulphur mustard gas was too toxic to be used in humans, Gilman hypothesized that by reducing the
1299:
Parker LJ, Ciccone S, Italiano LC, Primavera A, Oakley AJ, Morton CJ, et al. (June 2008). "The anti-cancer drug chlorambucil as a substrate for the human polymorphic enzyme glutathione transferase P1-1: kinetic properties and crystallographic characterisation of allelic variants".
887:
In the 1950s, aromatic mustards like chlorambucil were introduced as less toxic alkylating agents than the aliphatic nitrogen mustards, proving to be less electrophilic and react with DNA more slowly. Additionally, these agent can be administered orally, a significant advantage.
880:
electrophilicity of the agent, which made it highly chemically reactive towards electron-rich groups, then less toxic drugs could be obtained. To this end, he made analogues that were less electrophilic by exchanging the sulphur with a nitrogen, leading to the nitrogen mustards.
883:
With an acceptable therapeutic index in humans, nitrogen mustards were first introduced in the clinic in 1946. Aliphatic mustards were developed first, such as mechlorethamine hydrochloride (mustine hydrochloride), which is still used in the clinic today.
831:
Attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected
815:
Chlorambucil produces its anti-cancer effects by interfering with DNA replication and damaging the DNA in a cell. The DNA damage induces cell cycle arrest and cellular apoptosis via the accumulation of cytosolic
871:
Chlorambucil is a white to pale beige crystalline or granular powder with a slight odor. When heated to decomposition it emits very toxic fumes of hydrogen chloride and nitrogen oxides
827:
Chlorambucil alkylates and cross-links DNA during all phases of the cell cycle, inducing DNA damage via three different methods of covalent adduct generation with double-helical DNA:
1278:
1390:
Anslow WP, Karnofsky DA (May 1948). "The intravenous, subcutaneous and cutaneous toxicity of bis (beta-chloroethyl) sulfide (mustard gas) and of various derivatives".
850:
A recent study has shown
Chlorambucil to be detoxified by human glutathione transferase Pi (GST P1-1), an enzyme that is often found over-expressed in cancer tissues.
3033:
853:
This is important since
Chlorambucil, as an electrophile, is made less reactive by conjugation with glutathione, thereby making the drug less toxic to the cell.
695:
Chlorambucil's current use is mainly in chronic lymphocytic leukemia, as it is well tolerated by most patients, though chlorambucil has been largely replaced by
3212:
106:
863:
Shown above, Chlorambucil reacts with glutathione as catalyzed by hGSTA 1-1 leading to the formation of the monoglutathionyl derivative of
Chlorambucil.
1460:
945:
60:
3093:
2160:
750:) is the most commonly occurring side effect of chlorambucil. Withdrawn from the drug, this side effect is typically reversible. Like many
559:
1111:"Leukeran (Chlorambucil) Drug Information: Description, User Reviews, Drug Side Effects, Interactions – Prescribing Information at RxList"
1989:
1969:
1954:
1420:
1270:
988:
545:
2376:
1179:
3121:
1453:
680:
1354:
2743:
1147:
604:
1895:
1851:
1729:
1438:
3187:
1654:
1118:
579:
3138:
1446:
1204:
835:
DNA damage via the formation of cross-links which prevents DNA from being separated for synthesis or transcription.
704:
2170:
665:
227:
136:
3207:
2789:
1791:
1681:
298:
2711:
2694:
2569:
2333:
1711:
2443:
2039:
626:
468:
349:
2645:
909:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
842:
The precise mechanisms by which chlorambucil acts to kill tumor cells are not yet completely understood.
429:
2035:
2005:
3202:
3157:
1825:
821:
1930:
418:
3217:
3001:
2891:
2881:
1038:
1010:
908:
587:
InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)
3197:
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1834:
937:
445:
3126:
2866:
2581:
2067:
1915:
1842:
712:
645:
622:
92:
50:
2946:
2936:
2669:
2511:
1066:
Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, et al. (December 2000).
780:
720:
398:
2218:
1865:
1185:
from the original on 2015-12-22 – via emOnc.org - A Free
Hematology/Oncology Reference.
289:
1427:
1220:"Reprogramming the mechanism of action of chlorambucil by coupling to a G-quadruplex ligand"
1068:"Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia"
2616:
2493:
2014:
1347:"Chemical Approaches to the Discovery and Development of Cancer: Serendipity and Chemistry"
700:
634:
358:
196:
338:
8:
2901:
2801:
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638:
253:
244:
99:
472:
449:
1959:
1468:
1244:
1219:
724:
699:
as first-line treatment in younger patients. It can be used for treating some types of
657:
3192:
3068:
2657:
1491:
1399:
1327:
1249:
1089:
716:
708:
679:
Chlorambucil was approved for medical use in the United States in 1957. It is on the
84:
984:
856:
70:
3073:
2845:
2560:
2194:
2179:
1900:
1317:
1309:
1239:
1231:
1168:
1079:
1046:
1018:
751:
747:
735:
684:
630:
485:
166:
119:
754:, chlorambucil has been associated with the development of other forms of cancer.
3171:
2527:
2489:
2280:
1702:
1617:
278:
184:
174:
1084:
1067:
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793:
1313:
1139:
37:
3181:
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2351:
2224:
2105:
2048:
1806:
1755:
1043:
World Health
Organization model list of essential medicines: 22nd list (2021)
461:
151:
20:
648:. Other serious side effects include an increased long term risk of further
3053:
3017:
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1949:
1816:
1796:
1725:
1674:
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1478:
1470:
1403:
1331:
1253:
1093:
1015:
World Health
Organization model list of essential medicines: 21st list 2019
114:
1110:
3098:
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3058:
3043:
3006:
2981:
2926:
2896:
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1811:
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1507:
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78:
1051:
1023:
318:
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329:
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2401:
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2252:
2214:
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2136:
2126:
2098:
2058:
2019:
1994:
1984:
1944:
1590:
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1575:
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1532:
661:
264:
209:
64:
3012:
2986:
2931:
2699:
2637:
2417:
2313:
2285:
1964:
1801:
770:
766:
378:
309:
544:
1920:
1821:
1635:
1496:
1217:
838:
Induction of mispairing of the nucleotides leading to mutations.
1560:
784:
783:: Seizures, tremors, muscular twitching, confusion, agitation,
762:
739:
649:
409:
28:
1377:
1298:
668:
family of medications. It works by blocking the formation of
535:
389:
189:
723:
for various autoimmune and inflammatory conditions, such as
434:
1218:
Di
Antonio M, McLuckie KI, Balasubramanian S (April 2014).
369:
1065:
664:
often results in harm to the baby. Chlorambucil is in the
1392:
The
Journal of Pharmacology and Experimental Therapeutics
1037:
1009:
916:
817:
673:
669:
1027:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
1265:
1263:
681:
3155:
987:. The American Society of Health-System Pharmacists.
891:
Chlorambucil was first synthesized by Everett et al.
1374:
1260:
901:
637:. For CLL it is a preferred treatment. It is given
297:
845:
3179:
277:
1389:
252:
1375:Gilman AG, Rall TW, Nies AS, Taylor P (1990).
1344:
757:Less commonly occurring side effects include:
3213:World Health Organization essential medicines
1454:
855:
158:In general: ℞ (Prescription only)
1461:
1447:
979:
977:
975:
973:
971:
969:
967:
965:
963:
471:
448:
337:
36:
27:
1321:
1243:
1083:
1050:
1022:
357:
1224:Journal of the American Chemical Society
719:. Moreover, it also has been used as an
960:
444:
317:
83:
3180:
1031:
1003:
810:
462:
1442:
1277:. U.S. National Library of Medicine.
1045:. Geneva: World Health Organization.
1017:. Geneva: World Health Organization.
991:from the original on 21 December 2016
948:from the original on 21 December 2016
417:
397:
145:
69:
1434:. U.S. National Library of Medicine.
1105:
1103:
118:
1730:ribonucleotide reductase inhibitors
1140:"chlorambucil – CancerConnect News"
1072:The New England Journal of Medicine
377:
268:
13:
1896:Ribonucleotide reductase inhibitor
1852:Ribonucleotide reductase inhibitor
14:
3229:
1655:Dihydrofolate reductase inhibitor
1414:
1169:"Leukeran (chlorambucil) Tablets"
1100:
3165:
1207:from the original on 2017-01-03.
508:
502:
496:
1383:
1368:
1357:from the original on 2014-06-23
1338:
1292:
1281:from the original on 2015-12-22
1211:
1189:
1150:from the original on 2015-12-22
1121:from the original on 2015-12-22
805:
730:
690:
592:Key:JCKYGMPEJWAADB-UHFFFAOYSA-N
1792:Thymidylate synthase inhibitor
1682:Thymidylate synthase inhibitor
1345:Neidle S, Thurston DE (2006).
1161:
1132:
1059:
930:
846:Limitations to bioavailability
683:. It was originally made from
567:ClCCN(CCCl)c1ccc(cc1)CCCC(=O)O
511:
490:
1:
1712:Adenosine deaminase inhibitor
1553:Block microtubule disassembly
1271:"Chlorambucil | C14H19Cl2NO2"
894:
820:and subsequent activation of
705:Waldenström macroglobulinemia
1302:Journal of Molecular Biology
866:
644:Common side effects include
627:chronic lymphocytic leukemia
617:, sold under the brand name
7:
1085:10.1056/NEJM200012143432402
761:Gastrointestinal Distress (
10:
3234:
1055:. WHO/MHP/HPS/EML/2021.02.
874:
822:Bcl-2-associated X protein
480:Chemical and physical data
3116:
3002:Omacetaxine mepesuccinate
2892:Ciltacabtagene autoleucel
2882:Brexucabtagene autoleucel
2828:
2779:
2559:
2552:
2488:
2442:
2375:
2332:
2169:
2154:
2034:
2004:
1929:
1914:
1885:
1781:
1701:
1644:
1627:
1616:
1552:
1505:
1486:
1314:10.1016/j.jmb.2008.04.066
1039:World Health Organization
1011:World Health Organization
942:National Cancer Institute
824:, an apoptosis promoter.
600:
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135:
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91:
77:
59:
49:
44:
35:
26:
3188:IARC Group 1 carcinogens
3049:Talimogene laherparepvec
1916:Topoisomerase inhibitors
1835:DNA polymerase inhibitor
1423:(manufacturer's website)
2867:Axicabtagene ciloleucel
1471:chemotherapeutic agents
1432:Drug Information Portal
736:Bone marrow suppression
713:trophoblastic neoplasms
646:bone marrow suppression
623:chemotherapy medication
3034:Sitimagene ceradenovec
2947:Idecabtagene vicleucel
2512:Methyl aminolevulinate
860:
781:Central Nervous System
721:immunosuppressive drug
235:4-benzenebutanoic acid
3208:Chloroethyl compounds
2523:Porphyrin derivatives
2219:Melphalan flufenamide
1866:Hypomethylating agent
1475:antineoplastic agents
1379:. New York: Pergamon.
944:. 17 September 2014.
859:
787:, and hallucinations.
2852:Asparagine depleters
2781:Receptor antagonists
2695:+abiraterone acetate
701:non-Hodgkin lymphoma
635:non-Hodgkin lymphoma
2902:Denileukin diftitox
2802:Retinoid X receptor
2502:Aminolevulinic acid
2324:Triethylenemelamine
2156:Crosslinking of DNA
1887:Deoxyribonucleotide
1826:+gimeracil/oteracil
811:Mechanism of action
621:among others, is a
23:
3143:Never to phase III
1960:Etirinotecan pegol
1144:CancerConnect News
861:
725:nephrotic syndrome
658:allergic reactions
19:
3203:Nitrogen mustards
3153:
3152:
3112:
3111:
3069:Tigilanol tiglate
2561:Enzyme inhibitors
2484:
2483:
2480:
2479:
2180:Nitrogen mustards
2150:
2149:
1910:
1909:
1612:
1611:
1236:10.1021/ja5014344
1230:(16): 5860–5863.
1078:(24): 1750–1757.
752:alkylating agents
717:ovarian carcinoma
709:polycythemia vera
612:
611:
546:Interactive image
430:CompTox Dashboard
149:
16:Chemical compound
3225:
3218:Carboxylic acids
3170:
3169:
3168:
3161:
3074:Tisagenlecleucel
2846:Arsenic trioxide
2557:
2556:
2490:Photosensitizers
2281:Alkyl sulfonates
2195:Cyclophosphamide
2167:
2166:
2106:Anthracenediones
1927:
1926:
1901:Hydroxycarbamide
1642:
1641:
1625:
1624:
1503:
1502:
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996:
981:
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957:
955:
953:
934:
928:
927:
925:
923:
913:nctr-crs.fda.gov
905:
748:thrombocytopenia
685:nitrogen mustard
666:alkylating agent
631:Hodgkin lymphoma
608:
607:
548:
528:
513:
510:
504:
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154:
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144:
122:
87:
73:
55:Leukeran, others
40:
31:
24:
22:
18:
3233:
3232:
3228:
3227:
3226:
3224:
3223:
3222:
3198:Organochlorides
3178:
3177:
3176:
3166:
3164:
3156:
3154:
3149:
3148:
3133:Clinical trials
3108:
2829:Other/ungrouped
2824:
2775:
2548:
2528:Porfimer sodium
2476:
2438:
2371:
2328:
2158:
2146:
2030:
2000:
1918:
1906:
1881:
1777:
1697:
1633:
1631:antimetabolites
1629:
1628:DNA precursors/
1620:
1618:DNA replication
1608:
1548:
1518:Vinca alkaloids
1494:
1482:
1467:
1426:
1417:
1412:
1411:
1388:
1384:
1373:
1369:
1360:
1358:
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1293:
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1282:
1269:
1268:
1261:
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1212:
1195:
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1190:
1182:
1176:GlaxoSmithKline
1171:
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198:
175:Bioavailability
167:Pharmacokinetic
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94:
17:
12:
11:
5:
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2757:
2752:
2740:
2734:
2729:
2724:
2719:
2708:
2702:
2697:
2689:
2682:PARP inhibitor
2678:
2666:
2654:
2642:
2641:
2640:
2635:
2630:
2625:
2613:
2607:
2602:
2597:
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2578:
2565:
2563:
2554:
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2540:
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2440:
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2414:
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2379:
2373:
2372:
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2369:
2364:
2359:
2354:
2349:
2344:
2338:
2336:
2334:Platinum-based
2330:
2329:
2327:
2326:
2321:
2316:
2311:
2299:
2298:
2292:
2276:
2275:
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2207:
2201:
2192:
2187:
2175:
2173:
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2152:
2151:
2148:
2147:
2145:
2144:
2139:
2134:
2129:
2124:
2118:
2113:
2102:
2096:
2091:
2086:
2081:
2076:
2071:
2061:
2056:
2049:Anthracyclines
2044:
2042:
2032:
2031:
2029:
2028:
2022:
2010:
2008:
2002:
2001:
1999:
1998:
1992:
1987:
1982:
1977:
1972:
1967:
1962:
1957:
1952:
1947:
1935:
1933:
1924:
1912:
1911:
1908:
1907:
1905:
1904:
1891:
1889:
1883:
1882:
1880:
1879:
1873:
1861:
1860:
1847:
1846:
1830:
1829:
1819:
1814:
1809:
1804:
1799:
1787:
1785:
1779:
1778:
1776:
1775:
1769:
1767:Mercaptopurine
1758:
1753:
1748:
1742:
1737:
1721:
1720:
1707:
1705:
1699:
1698:
1696:
1695:
1689:
1678:
1672:
1667:
1662:
1650:
1648:
1639:
1622:
1614:
1613:
1610:
1609:
1607:
1606:
1594:
1588:
1583:
1578:
1573:
1568:
1556:
1554:
1550:
1549:
1547:
1546:
1540:
1535:
1530:
1525:
1513:
1511:
1500:
1484:
1483:
1469:Intracellular
1466:
1465:
1458:
1451:
1443:
1437:
1436:
1428:"Chlorambucil"
1424:
1416:
1415:External links
1413:
1410:
1409:
1382:
1367:
1337:
1308:(1): 131–144.
1291:
1259:
1210:
1197:"Chlorambucil"
1188:
1160:
1131:
1099:
1058:
1030:
1002:
985:"Chlorambucil"
959:
938:"Chlorambucil"
929:
899:
898:
896:
893:
876:
873:
868:
865:
847:
844:
840:
839:
836:
833:
812:
809:
807:
804:
803:
802:
799:
796:
794:Hepatotoxicity
791:
790:Skin reactions
788:
778:
732:
729:
692:
689:
625:used to treat
610:
609:
598:
597:
595:
594:
591:
589:
586:
578:
577:
576:
573:
572:
570:
569:
566:
558:
557:
556:
553:
552:
550:
549:
541:
539:
531:
530:
524:
518:
517:
514:
505:
499:
493:
488:
482:
481:
477:
476:
466:
458:
457:
455:
454:
441:
439:
426:
425:
423:
422:
414:
412:
406:
405:
403:
402:
394:
392:
386:
385:
383:
382:
374:
372:
366:
365:
363:
362:
354:
352:
346:
345:
343:
342:
334:
332:
326:
325:
323:
322:
314:
312:
306:
305:
303:
302:
294:
292:
286:
285:
283:
282:
274:
272:
261:
260:
258:
257:
249:
247:
241:
240:
238:
237:
234:
226:
225:
224:
221:
220:
216:
215:
212:
206:
205:
202:
193:
192:
187:
181:
180:
177:
171:
170:
163:
162:
160:
159:
156:
141:
139:
133:
132:
128:
127:
125:
124:
111:
109:
103:
102:
97:
95:administration
89:
88:
81:
75:
74:
67:
57:
56:
53:
47:
46:
42:
41:
33:
32:
15:
9:
6:
4:
3:
2:
3230:
3219:
3216:
3214:
3211:
3209:
3206:
3204:
3201:
3199:
3196:
3194:
3191:
3189:
3186:
3185:
3183:
3173:
3163:
3162:
3159:
3142:
3140:
3137:
3136:
3134:
3131:
3128:
3125:
3123:
3120:
3119:
3115:
3105:
3102:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3024:
3021:
3019:
3015:
3014:
3010:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2977:Lurbinectedin
2975:
2973:
2970:
2968:
2965:
2963:
2960:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2913:
2910:
2908:
2905:
2903:
2900:
2898:
2895:
2893:
2890:
2888:
2885:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2862:
2858:
2854:
2853:
2849:
2847:
2844:
2842:
2839:
2837:
2834:
2833:
2831:
2827:
2820:
2816:
2815:
2811:
2808:
2804:
2803:
2799:
2796:
2792:
2791:
2787:
2786:
2784:
2782:
2778:
2771:
2768:
2766:
2763:
2761:
2758:
2756:
2753:
2751:
2747:
2745:
2741:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2714:
2713:
2709:
2706:
2703:
2701:
2698:
2696:
2693:
2690:
2688:
2684:
2683:
2679:
2676:
2672:
2671:
2667:
2664:
2660:
2659:
2655:
2652:
2648:
2647:
2643:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2620:
2619:
2618:
2614:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2587:
2586:
2583:
2579:
2576:
2572:
2571:
2567:
2566:
2564:
2562:
2558:
2555:
2551:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2525:
2524:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2499:
2497:
2495:
2491:
2487:
2472:
2469:
2467:
2464:
2462:
2459:
2457:
2453:
2450:
2449:
2447:
2445:
2444:Intercalation
2441:
2434:
2431:
2429:
2426:
2424:
2420:
2419:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2397:
2393:
2392:
2388:
2386:
2383:
2382:
2380:
2378:
2374:
2368:
2365:
2363:
2360:
2358:
2355:
2353:
2352:Dicycloplatin
2350:
2348:
2345:
2343:
2340:
2339:
2337:
2335:
2331:
2325:
2322:
2320:
2317:
2315:
2312:
2310:
2307:
2305:
2301:
2300:
2296:
2293:
2291:
2287:
2284:
2282:
2278:
2277:
2274:
2271:
2269:
2266:
2264:
2261:
2258:
2254:
2251:
2249:
2246:
2244:
2241:
2239:
2235:
2234:
2231:
2228:
2226:
2225:Prednimustine
2223:
2220:
2216:
2213:
2211:
2208:
2205:
2202:
2200:
2196:
2193:
2191:
2188:
2186:
2183:
2181:
2177:
2176:
2174:
2172:
2168:
2165:
2162:
2157:
2153:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2122:
2119:
2117:
2114:
2112:
2108:
2107:
2103:
2100:
2097:
2095:
2092:
2090:
2087:
2085:
2082:
2080:
2077:
2075:
2072:
2069:
2065:
2062:
2060:
2057:
2055:
2051:
2050:
2046:
2045:
2043:
2041:
2040:Intercalation
2037:
2033:
2026:
2023:
2021:
2017:
2016:
2012:
2011:
2009:
2007:
2003:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1966:
1963:
1961:
1958:
1956:
1953:
1951:
1948:
1946:
1942:
1941:
1937:
1936:
1934:
1932:
1928:
1925:
1922:
1917:
1913:
1902:
1898:
1897:
1893:
1892:
1890:
1888:
1884:
1877:
1874:
1872:
1868:
1867:
1863:
1862:
1858:
1854:
1853:
1849:
1848:
1844:
1843:+daunorubicin
1841:
1837:
1836:
1832:
1831:
1827:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1807:Doxifluridine
1805:
1803:
1800:
1798:
1794:
1793:
1789:
1788:
1786:
1784:
1780:
1773:
1770:
1768:
1764:
1763:
1759:
1757:
1756:Rabacfosadine
1754:
1752:
1749:
1746:
1743:
1741:
1738:
1736:
1732:
1731:
1727:
1723:
1722:
1718:
1714:
1713:
1709:
1708:
1706:
1704:
1700:
1693:
1690:
1688:
1684:
1683:
1679:
1676:
1673:
1671:
1668:
1666:
1663:
1661:
1657:
1656:
1652:
1651:
1649:
1647:
1643:
1640:
1637:
1632:
1626:
1623:
1619:
1615:
1604:
1600:
1599:
1595:
1592:
1589:
1587:
1584:
1582:
1579:
1577:
1574:
1572:
1569:
1567:
1563:
1562:
1558:
1557:
1555:
1551:
1544:
1541:
1539:
1536:
1534:
1531:
1529:
1526:
1524:
1520:
1519:
1515:
1514:
1512:
1509:
1504:
1501:
1498:
1493:
1489:
1485:
1480:
1476:
1472:
1464:
1459:
1457:
1452:
1450:
1445:
1444:
1441:
1433:
1429:
1425:
1422:
1419:
1418:
1405:
1401:
1397:
1393:
1386:
1378:
1371:
1356:
1352:
1348:
1341:
1333:
1329:
1324:
1319:
1315:
1311:
1307:
1303:
1295:
1280:
1276:
1272:
1266:
1264:
1255:
1251:
1246:
1241:
1237:
1233:
1229:
1225:
1221:
1214:
1206:
1202:
1198:
1192:
1181:
1177:
1170:
1164:
1149:
1145:
1141:
1135:
1120:
1116:
1112:
1106:
1104:
1095:
1091:
1086:
1081:
1077:
1073:
1069:
1062:
1053:
1048:
1044:
1040:
1034:
1025:
1020:
1016:
1012:
1006:
990:
986:
980:
978:
976:
974:
972:
970:
968:
966:
964:
947:
943:
939:
933:
918:
914:
910:
904:
900:
892:
889:
885:
881:
872:
864:
858:
854:
851:
843:
837:
834:
830:
829:
828:
825:
823:
819:
800:
797:
795:
792:
789:
786:
782:
779:
776:
772:
768:
764:
760:
759:
758:
755:
753:
749:
745:
741:
737:
728:
726:
722:
718:
714:
710:
706:
702:
698:
688:
686:
682:
677:
675:
671:
667:
663:
660:. Use during
659:
655:
651:
647:
642:
640:
636:
632:
628:
624:
620:
616:
606:
599:
590:
585:
584:
581:
574:
565:
564:
561:
554:
547:
543:
542:
540:
537:
532:
525:
523:
519:
489:
487:
483:
478:
474:
470:
467:
465:
463:ECHA InfoCard
459:
451:
447:
446:DTXSID7020263
443:
442:
440:
431:
427:
420:
416:
415:
413:
411:
407:
400:
396:
395:
393:
391:
387:
380:
376:
375:
373:
371:
367:
360:
356:
355:
353:
351:
347:
340:
336:
335:
333:
331:
327:
320:
316:
315:
313:
311:
307:
300:
296:
295:
293:
291:
287:
280:
276:
275:
273:
266:
262:
255:
251:
250:
248:
246:
242:
233:
232:
229:
222:
217:
213:
211:
207:
203:
201:
194:
191:
188:
186:
182:
178:
176:
172:
168:
164:
157:
155:
143:
142:
140:
138:
134:
129:
121:
116:
113:
112:
110:
108:
104:
101:
98:
96:
90:
86:
82:
80:
76:
72:
68:
66:
62:
58:
54:
52:
48:
45:Clinical data
43:
39:
34:
30:
25:
3054:Tazemetostat
3018:Alitretinoin
3011:
2937:Estramustine
2917:Elsamitrucin
2907:Eflornithine
2861:Pegaspargase
2857:Asparaginase
2850:
2819:Testolactone
2812:
2800:
2788:
2742:
2727:Panobinostat
2710:
2680:
2668:
2656:
2644:
2615:
2580:
2568:
2521:
2517:Padeliporfin
2456:Dactinomycin
2452:Streptomyces
2433:Temozolomide
2428:Mitozolomide
2416:
2407:Mitobronitol
2396:Procarbazine
2389:
2377:Nonclassical
2302:
2279:
2273:Streptozocin
2238:Nitrosoureas
2236:
2210:Chlorambucil
2209:
2204:Trofosfamide
2190:Chlormethine
2185:Bendamustine
2178:
2116:Mitoxantrone
2111:Losoxantrone
2104:
2064:Daunorubicin
2047:
2013:
1950:Camptothecin
1938:
1894:
1864:
1850:
1833:
1817:Fluorouracil
1797:Capecitabine
1790:
1760:
1724:
1710:
1680:
1675:Pralatrexate
1665:Methotrexate
1653:
1596:
1559:
1516:
1431:
1395:
1391:
1385:
1376:
1370:
1359:. Retrieved
1350:
1340:
1305:
1301:
1294:
1283:. Retrieved
1274:
1227:
1223:
1213:
1200:
1191:
1175:
1163:
1152:. Retrieved
1143:
1134:
1123:. Retrieved
1114:
1075:
1071:
1061:
1052:10665/345533
1042:
1033:
1024:10665/325771
1014:
1005:
993:. Retrieved
950:. Retrieved
941:
932:
920:. Retrieved
912:
903:
890:
886:
882:
878:
870:
862:
852:
849:
841:
826:
814:
806:Pharmacology
756:
734:
731:Side effects
694:
691:Medical uses
678:
643:
618:
615:Chlorambucil
614:
613:
602:
197:Elimination
137:Legal status
131:Legal status
21:Chlorambucil
3129:from market
3099:Vorasidenib
3079:Trabectedin
3064:Tiazofurine
3059:Tebentafusp
3044:Tagraxofusp
3007:Plitidepsin
2982:Mitoguazone
2927:Epacadostat
2897:Demecolcine
2841:Aflibercept
2814:Sex steroid
2687:Fuzuloparib
2628:Carfilzomib
2600:Palbociclib
2590:Abemaciclib
2543:Verteporfin
2507:Efaproxiral
2423:Dacarbazine
2385:Altretamine
2367:Satraplatin
2362:Oxaliplatin
2342:Carboplatin
2319:Triaziquone
2290:Mannosulfan
2268:Ranimustine
2248:Fotemustine
2089:Pirarubicin
2074:Doxorubicin
2068:+cytarabine
2054:Aclarubicin
2015:Podophyllum
1940:Camptotheca
1871:Azacitidine
1857:Gemcitabine
1812:Floxuridine
1745:Fludarabine
1740:Clofarabine
1726:Halogenated
1717:Pentostatin
1692:Raltitrexed
1660:Aminopterin
1603:Ixabepilone
1598:Epothilones
1566:Cabazitaxel
1543:Vinorelbine
1528:Vincristine
1523:Vinblastine
1508:microtubule
1323:2108/101037
952:19 December
798:Infertility
775:ulcerations
773:, and oral
744:neutropenia
697:fludarabine
654:infertility
529: g·mol
469:100.005.603
399:CHEBI:28830
219:Identifiers
79:MedlinePlus
51:Trade names
3182:Categories
3094:Verdinexor
3089:Venetoclax
2997:Oblimersen
2992:Navitoclax
2972:Lucanthone
2967:Lonidamine
2962:Lifileucel
2957:Ivosidenib
2952:Imetelstat
2922:Enasidenib
2912:Elesclomol
2877:Bexarotene
2872:Belzutifan
2807:Bexarotene
2795:Atrasentan
2770:Umbralisib
2765:Idelalisib
2755:Copanlisib
2737:Vorinostat
2732:Romidepsin
2722:Entinostat
2717:Belinostat
2675:Masoprocol
2663:Tiazofurin
2651:Anagrelide
2623:Bortezomib
2610:Seliciclib
2605:Ribociclib
2585:inhibitors
2575:Tipifarnib
2538:Temoporfin
2533:Talaporfin
2471:Plicamycin
2466:Mitomycins
2412:Pipobroman
2391:Hydrazines
2357:Nedaplatin
2309:Carboquone
2304:Aziridines
2295:Treosulfan
2243:Carmustine
2230:Uramustine
2199:Ifosfamide
2171:Alkylating
2132:Bisantrene
2121:Pixantrone
2094:Valrubicin
2084:Idarubicin
2079:Epirubicin
2025:Teniposide
1980:Lurtotecan
1975:Irinotecan
1876:Decitabine
1840:Cytarabine
1783:Pyrimidine
1772:Tioguanine
1762:Thiopurine
1751:Nelarabine
1735:Cladribine
1687:Pemetrexed
1670:Pemetrexed
1646:Folic acid
1586:Paclitaxel
1538:Vinflunine
1398:(1): 1–9.
1361:2016-11-24
1285:2015-12-21
1154:2015-12-21
1125:2015-12-21
995:8 December
895:References
534:3D model (
522:Molar mass
359:18D0SL7309
330:ChemSpider
290:IUPHAR/BPS
245:CAS Number
228:IUPAC name
185:Metabolism
3139:Phase III
3127:Withdrawn
3104:Vosaroxin
3084:Veliparib
3039:Sotorasib
3029:Selinexor
3023:Tretinoin
3013:Retinoids
2942:Glasdegib
2887:Celecoxib
2836:Adagrasib
2760:Duvelisib
2750:Alpelisib
2705:Rucaparib
2692:Niraparib
2633:Oprozomib
2595:Alvocidib
2461:Bleomycin
2418:Triazenes
2402:Etoglucid
2347:Cisplatin
2263:Nimustine
2257:Semustine
2253:Lomustine
2215:Melphalan
2142:Menogaril
2137:Crisnatol
2127:Amsacrine
2099:Zorubicin
2059:Amrubicin
2020:Etoposide
1995:Topotecan
1990:Silatecan
1985:Rubitecan
1970:Gimatecan
1955:Cositecan
1945:Belotecan
1621:inhibitor
1591:Tesetaxel
1581:Ortataxel
1576:Larotaxel
1571:Docetaxel
1533:Vindesine
1201:Drug Bank
867:Chemistry
801:Hair Loss
662:pregnancy
419:ChEMBL515
210:Excretion
204:1.5 hours
199:half-life
93:Routes of
71:Monograph
65:Drugs.com
3193:Anilines
3172:Medicine
2987:Mitotane
2932:Eribulin
2700:Olaparib
2638:Ixazomib
2314:Thiotepa
2286:Busulfan
1965:Exatecan
1802:Carmofur
1510:assembly
1473: /
1421:Leukeran
1404:18865181
1355:Archived
1332:18511072
1279:Archived
1254:24697838
1205:Archived
1180:Archived
1148:Archived
1119:Archived
1094:11114313
1041:(2021).
1013:(2019).
989:Archived
946:Archived
771:diarrhea
767:vomiting
639:by mouth
619:Leukeran
605:(verify)
310:DrugBank
254:305-03-3
107:ATC code
100:By mouth
1921:S phase
1822:Tegafur
1636:S phase
1561:Taxanes
1497:M phase
1351:Medcape
1275:PubChem
1245:4132976
875:History
629:(CLL),
486:Formula
319:DB00291
265:PubChem
153:WARNING
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117: (
115:L01AA02
85:a682899
3158:Portal
3122:WHO-EM
2746:(Pi3K)
1703:Purine
1506:Block
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1115:RxList
1092:
922:22 Oct
785:ataxia
763:nausea
740:anemia
715:, and
656:, and
650:cancer
633:, and
560:SMILES
527:304.21
410:ChEMBL
379:D00266
150:
2658:IMPDI
2553:Other
1183:(PDF)
1172:(PDF)
580:InChI
536:JSmol
390:ChEBI
190:Liver
2744:PIKI
2712:HDAC
2161:CCNS
1400:PMID
1328:PMID
1250:PMID
1090:PMID
997:2016
954:2016
924:2023
832:DNA.
672:and
370:KEGG
350:UNII
339:2607
299:7143
279:2708
169:data
61:AHFS
2790:ERA
2646:PhI
2617:PrI
2582:CDK
2494:PDT
1492:MIs
1488:SPs
1479:L01
1318:hdl
1310:doi
1306:380
1240:PMC
1232:doi
1228:136
1080:doi
1076:343
1047:hdl
1019:hdl
917:FDA
818:p53
674:RNA
670:DNA
435:EPA
269:CID
214:N/A
120:WHO
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