552:
529:
40:
940:
31:
3529:
1379:
815:
In August 2023, the US Food and Drug
Administration approved melphalan (Hepzato) as a liver-directed treatment for adults with uveal melanoma with unresectable hepatic metastases affecting less than 50% of the liver and no extrahepatic disease, or extrahepatic disease limited to the bone, lymph
812:. In the European Union, it is indicated, in combination with other cytotoxic medicinal products, as reduced intensity conditioning treatment prior to allogeneic haematopoietic stem cell transplantation in malignant haematological diseases in adults.
1024:(EMA) adopted a positive opinion, recommending the granting of a marketing authorization for melphalan. The applicant for this medicinal product is Adienne S.r.l. S.U. Melphalan was approved for medical use in the European Union in November 2020.
1396:
796:
for the treatment of multiple myeloma; malignant lymphoma (Hodgkin, non-Hodgkin lymphoma); acute lymphoblastic and myeloblastic leukemia; childhood neuroblastoma; ovarian cancer; and mammary adenocarcinoma.
1463:
Bergel F, Burnop VC, Stock JA (1955). "Cyto-active amino-acids and peptides. Part II. Resolution of para-substituted phenylalanines and synthesis of p-di-(2-chloroethyl)amino-DL-phenylalanine".
1486:
Larionov LF, Khokhlov AS, Shkodinskaja EN, Vasina OS, Troosheikina VI, Novikova MA (1955). "Studies on the anti-tumour activity of p-di-(2-chloroethyl) aminophenylalanine (sarcolysine)".
956:
205:
1070:
3480:
3440:
3407:
3145:
3475:
3455:
3435:
1356:
3569:
1397:"Delcath Systems, Inc. Announces FDA Approval of Hepzato Kit for the Treatment of Adult Patients with Unresectable Hepatic-Dominant Metastatic Uveal Melanoma"
160:
3412:
801:
3450:
3372:
1572:
153:
627:
3417:
1017:
1544:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1196:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
76:
3496:
3205:
2272:
641:
3402:
3289:
2101:
2081:
2066:
3460:
3354:
3349:
3344:
3339:
3334:
3506:
805:
1130:
1099:
2488:
3233:
1565:
777:
1326:
2855:
2007:
1963:
1841:
1550:
3554:
1766:
1310:
686:
661:
127:
3250:
1558:
3282:
2282:
1440:
Bergel F, Stock JA (1954). "Cyto-active amino-acid and peptide derivatives. Part I. Substituted phenylalanines".
762:
669:
InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
302:
190:
108:
3549:
2901:
1903:
1793:
1155:
377:
2823:
2806:
2681:
2445:
1823:
2555:
2151:
1362:
1332:
547:
428:
1524:
2757:
1042:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
508:
2147:
2117:
3559:
3519:
3275:
1937:
2042:
497:
3113:
3003:
2993:
1529:
1274:
1181:
1041:
1021:
3564:
3160:
2696:
1946:
878:
524:
3445:
3238:
2978:
2693:
2179:
2027:
1954:
747:
704:
138:
52:
3324:
3319:
3314:
3058:
3048:
2781:
2623:
992:
1071:"Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017"
477:
3574:
2330:
1977:
1176:
740:
716:
368:
417:
3470:
3364:
2728:
2605:
2126:
437:
268:
758:. Use during pregnancy may result in harm to the fetus. Melphalan belongs to the class of
8:
3013:
2913:
2892:
2613:
2435:
2267:
1998:
1894:
736:
551:
528:
332:
323:
149:
145:
2071:
1580:
976:
867:
781:
712:
1499:
3180:
2769:
1603:
1503:
1306:
996:
862:
100:
1418:
987:). Catalytic hydrogenation produced the corresponding aniline. Heating in acid with
870:(scarring of lung tissue) including fatal outcomes (usually only with prolonged use)
3501:
3387:
3298:
3185:
2957:
2672:
2306:
2291:
2012:
1495:
1468:
1445:
1282:
848:
809:
759:
708:
564:
357:
240:
173:
893:
Irreversible bone marrow failure due to melphalan not being withdrawn early enough
776:
Melphalan was approved for medical use in the United States in 1964. It is on the
3533:
2639:
2601:
2392:
1814:
1729:
1249:
1223:
816:
nodes, subcutaneous tissues, or lung that is amenable to resection or radiation.
258:
248:
86:
919:, and causes linkages between strands of DNA. This chemical alteration inhibits
3244:
2793:
2384:
1878:
1742:
1629:
1599:
1586:
896:
732:
728:
724:
951:
945:
3543:
3088:
2463:
2336:
2217:
2160:
1918:
1867:
1383:
995:
provided the bischloride, and removal of the protecting groups by heating in
964:
924:
920:
720:
540:
218:
3392:
3382:
3377:
3165:
3129:
3028:
3018:
2972:
2968:
2930:
2838:
2628:
2567:
2563:
2544:
2539:
2518:
2507:
2321:
2315:
2301:
2296:
2227:
2222:
2175:
2061:
1928:
1908:
1837:
1786:
1776:
1590:
1582:
1507:
1279:
World Health
Organization model list of essential medicines: 21st list 2019
1156:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/201848s000lbl.pdf
928:
168:
39:
22:
3210:
3190:
3175:
3170:
3155:
3118:
3093:
3038:
3008:
2952:
2925:
2798:
2739:
2711:
2701:
2654:
2618:
2534:
2496:
2478:
2473:
2453:
2430:
2401:
2379:
2359:
2349:
2200:
2185:
2165:
2051:
1982:
1968:
1923:
1856:
1851:
1828:
1803:
1771:
1714:
1677:
1654:
1639:
1634:
1619:
1472:
1449:
972:
833:
751:
94:
1287:
397:
3427:
3200:
3108:
3103:
3083:
3078:
3073:
3068:
3063:
3033:
3023:
2988:
2983:
2963:
2918:
2906:
2881:
2876:
2866:
2848:
2843:
2833:
2828:
2786:
2774:
2762:
2734:
2721:
2716:
2686:
2649:
2644:
2582:
2577:
2523:
2468:
2420:
2406:
2354:
2341:
2310:
2243:
2232:
2205:
2195:
2190:
2136:
2091:
2086:
1987:
1951:
1883:
1873:
1862:
1846:
1798:
1781:
1757:
1709:
1697:
1649:
916:
839:
603:
408:
939:
3215:
3195:
3150:
3140:
3134:
3053:
2998:
2947:
2871:
2861:
2816:
2803:
2744:
2706:
2634:
2572:
2513:
2502:
2458:
2415:
2374:
2368:
2364:
2253:
2248:
2238:
2210:
2170:
2131:
2106:
2096:
2056:
1702:
1692:
1687:
1682:
1644:
1357:"Oncology (Cancer) / Hematologic Malignancies Approval Notifications"
843:
793:
343:
281:
80:
3267:
3306:
3124:
3098:
3043:
2811:
2749:
2529:
2425:
2397:
2076:
1913:
888:
873:
457:
388:
122:
1485:
626:
2032:
1933:
1747:
1608:
1382:
This article incorporates text from this source, which is in the
1131:"Evomela- melphalan injection, powder, lyophilized, for solution"
988:
912:
755:
1519:
1517:
927:, functions necessary for cells to survive. These changes cause
3329:
1672:
828:
488:
286:
3465:
1514:
1305:(76 ed.). Pharmaceutical Press. 2018. pp. 873–874.
980:
617:
468:
513:
30:
883:
448:
1273:
1049:
908:
770:
766:
1327:"Evomela (Captisol-enabled melphalan HCl) for Injection"
1291:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
800:
In the United States, melphalan is used as a high-dose
778:
3517:
806:
hematopoietic progenitor (stem) cell transplantation
1125:
1123:
1121:
1094:
1092:
1034:
376:
1462:
3541:
1399:(Press release). Delcath Systems. 14 August 2023
1149:
1118:
1089:
356:
1230:. American Society of Health-System Pharmacists
1171:
1169:
1167:
1165:
1163:
931:in both dividing and non-dividing tumor cells.
765:. It works by interfering with the creation of
331:
1018:Committee for Medicinal Products for Human Use
3570:World Health Organization essential medicines
3283:
1566:
1160:
126:
1439:
3290:
3276:
1573:
1559:
1218:
1216:
1214:
1212:
1210:
1208:
1206:
1204:
1202:
550:
527:
416:
1465:Journal of the Chemical Society (Resumed)
1442:Journal of the Chemical Society (Resumed)
1286:
436:
1303:British national formulary : BNF 76
1100:"Alkeran- melphalan tablet, film coated"
938:
750:. Other severe side effects may include
1224:"Melphalan Monograph for Professionals"
1199:
746:Common side effects include nausea and
523:
396:
99:
3542:
1267:
1075:Therapeutic Goods Administration (TGA)
1006:
979:, and this was converted to its ethyl
902:
541:
227:
3297:
3271:
1554:
1295:
1281:. Geneva: World Health Organization.
496:
476:
212:
117:
85:
792:In the European Union, melphalan is
172:
70:)-2-amino-3-{4-phenyl}propanoic acid
1842:ribonucleotide reductase inhibitors
456:
347:
13:
2008:Ribonucleotide reductase inhibitor
1964:Ribonucleotide reductase inhibitor
857:Less common side effects include:
851:causing increased risk of bleeding
263:Hydrolysis to inactive metabolites
57:Alkeran, Evomela, Phelinun, others
14:
3586:
1767:Dihydrofolate reductase inhibitor
199:
3527:
1377:
1250:"Melphalan Use During Pregnancy"
907:Melphalan chemically alters the
840:Decreased white blood cell count
587:
581:
575:
38:
29:
1525:"Phelinun: Pending EC decision"
1479:
1456:
1433:
1411:
1389:
1349:
1319:
1011:
819:
787:
674:Key:SGDBTWWWUNNDEQ-LBPRGKRZSA-N
649:c1cc(ccc1C(C(=O)O)N)N(CCCl)CCCl
1904:Thymidylate synthase inhibitor
1794:Thymidylate synthase inhibitor
1242:
1063:
593:
569:
1:
3481:Propylbenzilylcholine mustard
1824:Adenosine deaminase inhibitor
1665:Block microtubule disassembly
1500:10.1016/S0140-6736(55)92736-7
1027:
991:, followed by treatment with
824:Common side effects include:
754:and the development of other
1363:Food and Drug Administration
1333:Food and Drug Administration
934:
699:, sold under the brand name
7:
1421:. National Cancer Institute
10:
3591:
3441:Acetylethylcholine mustard
1016:On 17 September 2020, the
842:causing increased risk of
559:Chemical and physical data
3489:
3426:
3363:
3305:
3228:
3114:Omacetaxine mepesuccinate
3004:Ciltacabtagene autoleucel
2994:Brexucabtagene autoleucel
2940:
2891:
2671:
2664:
2600:
2554:
2487:
2444:
2281:
2266:
2146:
2116:
2041:
2026:
1997:
1893:
1813:
1756:
1739:
1728:
1664:
1617:
1598:
1530:European Medicines Agency
1275:World Health Organization
1182:European Medicines Agency
1022:European Medicines Agency
682:
657:
637:
615:
602:
563:
558:
539:
507:
487:
467:
447:
427:
407:
387:
367:
342:
322:
298:
293:
280:
267:
257:
247:
239:
189:
184:
159:
137:
107:
93:
75:
61:
51:
46:
37:
28:
3555:IARC Group 1 carcinogens
3408:Phenylenediamine mustard
3161:Talimogene laherparepvec
2028:Topoisomerase inhibitors
1947:DNA polymerase inhibitor
1407:– via PR Newswire.
879:Interstitial pneumonitis
849:Decreased platelet count
3446:Benzilylcholine mustard
2979:Axicabtagene ciloleucel
1583:chemotherapeutic agents
971:) was converted to its
836:suppression, including
780:. It is available as a
748:bone marrow suppression
705:chemotherapy medication
3146:Sitimagene ceradenovec
3059:Idecabtagene vicleucel
2624:Methyl aminolevulinate
993:phosphorus oxychloride
960:
3550:Chloroethyl compounds
3476:Hemicholinium mustard
3456:Decamethonium mustard
3436:Acetylcholine mustard
3365:Antineoplastic agents
2635:Porphyrin derivatives
2331:Melphalan flufenamide
1978:Hypomethylating agent
1587:antineoplastic agents
952:U.S. patent 3,032,585
946:U.S. patent 3,032,584
942:
741:injection into a vein
717:myeloblastic leukemia
3471:Ethylcholine mustard
2964:Asparagine depleters
2893:Receptor antagonists
2807:+abiraterone acetate
1473:10.1039/JR9550001223
1450:10.1039/JR9540002409
715:; lymphoblastic and
3014:Denileukin diftitox
2914:Retinoid X receptor
2614:Aminolevulinic acid
2436:Triethylenemelamine
2268:Crosslinking of DNA
1999:Deoxyribonucleotide
1938:+gimeracil/oteracil
1534:. 18 September 2020
1186:. 15 September 2020
1007:Society and culture
903:Mechanism of action
804:treatment prior to
703:among others, is a
208:(Prescription only)
25:
3413:Quinacrine mustard
3255:Never to phase III
2072:Etirinotecan pegol
1337:. 30 November 2016
1137:. 31 December 2021
1106:. 18 November 2019
977:phthalic anhydride
961:
868:Pulmonary fibrosis
863:allergic reactions
782:generic medication
713:malignant lymphoma
21:
3560:Nitrogen mustards
3515:
3514:
3299:Nitrogen mustards
3265:
3264:
3224:
3223:
3181:Tigilanol tiglate
2673:Enzyme inhibitors
2596:
2595:
2592:
2591:
2292:Nitrogen mustards
2262:
2261:
2022:
2021:
1724:
1723:
997:hydrochloric acid
763:alkylating agents
694:
693:
628:Interactive image
509:CompTox Dashboard
313:
253:25–89% (By mouth)
231:
216:
203:
120:
71:
16:Chemical compound
3582:
3532:
3531:
3530:
3523:
3502:Phenoxybenzamine
3388:Cyclophosphamide
3292:
3285:
3278:
3269:
3268:
3186:Tisagenlecleucel
2958:Arsenic trioxide
2669:
2668:
2602:Photosensitizers
2393:Alkyl sulfonates
2307:Cyclophosphamide
2279:
2278:
2218:Anthracenediones
2039:
2038:
2013:Hydroxycarbamide
1754:
1753:
1737:
1736:
1615:
1614:
1575:
1568:
1561:
1552:
1551:
1545:
1543:
1541:
1539:
1521:
1512:
1511:
1494:(6882): 169–71.
1483:
1477:
1476:
1460:
1454:
1453:
1437:
1431:
1430:
1428:
1426:
1415:
1409:
1408:
1406:
1404:
1393:
1387:
1381:
1380:
1376:
1374:
1372:
1367:. 14 August 2023
1353:
1347:
1346:
1344:
1342:
1323:
1317:
1316:
1299:
1293:
1292:
1290:
1271:
1265:
1264:
1262:
1260:
1246:
1240:
1239:
1237:
1235:
1220:
1197:
1195:
1193:
1191:
1173:
1158:
1153:
1147:
1146:
1144:
1142:
1127:
1116:
1115:
1113:
1111:
1096:
1087:
1086:
1084:
1082:
1067:
1061:
1060:
1058:
1056:
1046:nctr-crs.fda.gov
1038:
999:gave melphalan (
975:by heating with
954:
948:
810:multiple myeloma
760:nitrogen mustard
709:multiple myeloma
690:
689:
630:
610:
595:
589:
583:
577:
571:
554:
543:
532:
531:
517:
515:
500:
480:
460:
440:
420:
400:
380:
360:
350:
349:
335:
311:
272:
229:
226:
221:
214:
211:
201:
198:
176:
130:
119:
116:
103:
89:
65:
42:
33:
26:
24:
20:
3590:
3589:
3585:
3584:
3583:
3581:
3580:
3579:
3565:Specialty drugs
3540:
3539:
3538:
3528:
3526:
3518:
3516:
3511:
3485:
3451:Choline mustard
3422:
3373:Aniline mustard
3359:
3301:
3296:
3266:
3261:
3260:
3245:Clinical trials
3220:
2941:Other/ungrouped
2936:
2887:
2660:
2640:Porfimer sodium
2588:
2550:
2483:
2440:
2270:
2258:
2142:
2112:
2030:
2018:
1993:
1889:
1809:
1745:
1743:antimetabolites
1741:
1740:DNA precursors/
1732:
1730:DNA replication
1720:
1660:
1630:Vinca alkaloids
1606:
1594:
1579:
1549:
1548:
1537:
1535:
1523:
1522:
1515:
1484:
1480:
1461:
1457:
1438:
1434:
1424:
1422:
1417:
1416:
1412:
1402:
1400:
1395:
1394:
1390:
1378:
1370:
1368:
1355:
1354:
1350:
1340:
1338:
1325:
1324:
1320:
1313:
1301:
1300:
1296:
1272:
1268:
1258:
1256:
1248:
1247:
1243:
1233:
1231:
1222:
1221:
1200:
1189:
1187:
1177:"Phelinun EPAR"
1175:
1174:
1161:
1154:
1150:
1140:
1138:
1129:
1128:
1119:
1109:
1107:
1098:
1097:
1090:
1080:
1078:
1069:
1068:
1064:
1054:
1052:
1040:
1039:
1035:
1030:
1014:
1009:
950:
944:
937:
905:
822:
808:in people with
790:
685:
683:
678:
675:
670:
665:
664:
653:
650:
645:
644:
633:
608:
598:
592:
586:
580:
574:
535:
511:
503:
483:
463:
443:
423:
403:
383:
363:
346:
338:
318:
315:
306:
305:
289:(IV: 5.8–21.3%)
276:1.5 ± 0.8 hours
270:
249:Bioavailability
241:Pharmacokinetic
235:
219:
180:
140:
133:
17:
12:
11:
5:
3588:
3578:
3577:
3572:
3567:
3562:
3557:
3552:
3537:
3536:
3513:
3512:
3510:
3509:
3504:
3499:
3493:
3491:
3487:
3486:
3484:
3483:
3478:
3473:
3468:
3463:
3458:
3453:
3448:
3443:
3438:
3432:
3430:
3424:
3423:
3421:
3420:
3415:
3410:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3369:
3367:
3361:
3360:
3358:
3357:
3352:
3347:
3342:
3337:
3332:
3327:
3322:
3317:
3311:
3309:
3303:
3302:
3295:
3294:
3287:
3280:
3272:
3263:
3262:
3259:
3258:
3257:
3256:
3253:
3242:
3236:
3230:
3229:
3226:
3225:
3222:
3221:
3219:
3218:
3213:
3208:
3203:
3198:
3193:
3188:
3183:
3178:
3173:
3168:
3163:
3158:
3153:
3148:
3143:
3138:
3132:
3121:
3116:
3111:
3106:
3101:
3096:
3091:
3086:
3081:
3076:
3071:
3066:
3061:
3056:
3051:
3046:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2996:
2991:
2986:
2981:
2976:
2960:
2955:
2950:
2944:
2942:
2938:
2937:
2935:
2934:
2922:
2910:
2897:
2895:
2889:
2888:
2886:
2885:
2879:
2874:
2869:
2864:
2852:
2846:
2841:
2836:
2831:
2820:
2814:
2809:
2801:
2794:PARP inhibitor
2790:
2778:
2766:
2754:
2753:
2752:
2747:
2742:
2737:
2725:
2719:
2714:
2709:
2704:
2690:
2677:
2675:
2666:
2662:
2661:
2659:
2658:
2652:
2647:
2642:
2631:
2626:
2621:
2616:
2610:
2608:
2598:
2597:
2594:
2593:
2590:
2589:
2587:
2586:
2580:
2575:
2570:
2560:
2558:
2552:
2551:
2549:
2548:
2542:
2537:
2526:
2521:
2516:
2511:
2499:
2493:
2491:
2485:
2484:
2482:
2481:
2476:
2471:
2466:
2461:
2456:
2450:
2448:
2446:Platinum-based
2442:
2441:
2439:
2438:
2433:
2428:
2423:
2411:
2410:
2404:
2388:
2387:
2382:
2377:
2372:
2362:
2357:
2345:
2344:
2339:
2334:
2324:
2319:
2313:
2304:
2299:
2287:
2285:
2276:
2264:
2263:
2260:
2259:
2257:
2256:
2251:
2246:
2241:
2236:
2230:
2225:
2214:
2208:
2203:
2198:
2193:
2188:
2183:
2173:
2168:
2161:Anthracyclines
2156:
2154:
2144:
2143:
2141:
2140:
2134:
2122:
2120:
2114:
2113:
2111:
2110:
2104:
2099:
2094:
2089:
2084:
2079:
2074:
2069:
2064:
2059:
2047:
2045:
2036:
2024:
2023:
2020:
2019:
2017:
2016:
2003:
2001:
1995:
1994:
1992:
1991:
1985:
1973:
1972:
1959:
1958:
1942:
1941:
1931:
1926:
1921:
1916:
1911:
1899:
1897:
1891:
1890:
1888:
1887:
1881:
1879:Mercaptopurine
1870:
1865:
1860:
1854:
1849:
1833:
1832:
1819:
1817:
1811:
1810:
1808:
1807:
1801:
1790:
1784:
1779:
1774:
1762:
1760:
1751:
1734:
1726:
1725:
1722:
1721:
1719:
1718:
1706:
1700:
1695:
1690:
1685:
1680:
1668:
1666:
1662:
1661:
1659:
1658:
1652:
1647:
1642:
1637:
1625:
1623:
1612:
1596:
1595:
1581:Intracellular
1578:
1577:
1570:
1563:
1555:
1547:
1546:
1513:
1478:
1455:
1432:
1410:
1388:
1348:
1318:
1311:
1294:
1266:
1241:
1198:
1159:
1148:
1117:
1088:
1077:. 21 June 2022
1062:
1032:
1031:
1029:
1026:
1020:(CHMP) of the
1013:
1010:
1008:
1005:
955:(both 1962 to
936:
933:
904:
901:
900:
899:
897:Cardiac arrest
894:
891:
886:
881:
876:
871:
865:
855:
854:
853:
852:
846:
831:
821:
818:
789:
786:
735:. It is taken
733:uveal melanoma
729:adenocarcinoma
725:ovarian cancer
707:used to treat
692:
691:
680:
679:
677:
676:
673:
671:
668:
660:
659:
658:
655:
654:
652:
651:
648:
640:
639:
638:
635:
634:
632:
631:
623:
621:
613:
612:
606:
600:
599:
596:
590:
584:
578:
572:
567:
561:
560:
556:
555:
545:
537:
536:
534:
533:
520:
518:
505:
504:
502:
501:
493:
491:
485:
484:
482:
481:
473:
471:
465:
464:
462:
461:
453:
451:
445:
444:
442:
441:
433:
431:
425:
424:
422:
421:
413:
411:
405:
404:
402:
401:
393:
391:
385:
384:
382:
381:
373:
371:
365:
364:
362:
361:
353:
351:
340:
339:
337:
336:
328:
326:
320:
319:
317:
316:
314:-phenylalanine
309:
301:
300:
299:
296:
295:
291:
290:
284:
278:
277:
274:
265:
264:
261:
255:
254:
251:
245:
244:
237:
236:
234:
233:
224:
209:
195:
193:
187:
186:
182:
181:
179:
178:
165:
163:
157:
156:
154:intra-arterial
143:
141:administration
135:
134:
132:
131:
113:
111:
105:
104:
97:
91:
90:
83:
73:
72:
63:
59:
58:
55:
49:
48:
44:
43:
35:
34:
15:
9:
6:
4:
3:
2:
3587:
3576:
3573:
3571:
3568:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3547:
3545:
3535:
3525:
3524:
3521:
3508:
3505:
3503:
3500:
3498:
3495:
3494:
3492:
3488:
3482:
3479:
3477:
3474:
3472:
3469:
3467:
3464:
3462:
3459:
3457:
3454:
3452:
3449:
3447:
3444:
3442:
3439:
3437:
3434:
3433:
3431:
3429:
3425:
3419:
3416:
3414:
3411:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3370:
3368:
3366:
3362:
3356:
3353:
3351:
3348:
3346:
3343:
3341:
3338:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3312:
3310:
3308:
3304:
3300:
3293:
3288:
3286:
3281:
3279:
3274:
3273:
3270:
3254:
3252:
3249:
3248:
3246:
3243:
3240:
3237:
3235:
3232:
3231:
3227:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3177:
3174:
3172:
3169:
3167:
3164:
3162:
3159:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3136:
3133:
3131:
3127:
3126:
3122:
3120:
3117:
3115:
3112:
3110:
3107:
3105:
3102:
3100:
3097:
3095:
3092:
3090:
3089:Lurbinectedin
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:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2990:
2987:
2985:
2982:
2980:
2977:
2974:
2970:
2966:
2965:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2945:
2943:
2939:
2932:
2928:
2927:
2923:
2920:
2916:
2915:
2911:
2908:
2904:
2903:
2899:
2898:
2896:
2894:
2890:
2883:
2880:
2878:
2875:
2873:
2870:
2868:
2865:
2863:
2859:
2857:
2853:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2826:
2825:
2821:
2818:
2815:
2813:
2810:
2808:
2805:
2802:
2800:
2796:
2795:
2791:
2788:
2784:
2783:
2779:
2776:
2772:
2771:
2767:
2764:
2760:
2759:
2755:
2751:
2748:
2746:
2743:
2741:
2738:
2736:
2733:
2732:
2731:
2730:
2726:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2699:
2698:
2695:
2691:
2688:
2684:
2683:
2679:
2678:
2676:
2674:
2670:
2667:
2663:
2656:
2653:
2651:
2648:
2646:
2643:
2641:
2637:
2636:
2632:
2630:
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2611:
2609:
2607:
2603:
2599:
2584:
2581:
2579:
2576:
2574:
2571:
2569:
2565:
2562:
2561:
2559:
2557:
2556:Intercalation
2553:
2546:
2543:
2541:
2538:
2536:
2532:
2531:
2527:
2525:
2522:
2520:
2517:
2515:
2512:
2509:
2505:
2504:
2500:
2498:
2495:
2494:
2492:
2490:
2486:
2480:
2477:
2475:
2472:
2470:
2467:
2465:
2464:Dicycloplatin
2462:
2460:
2457:
2455:
2452:
2451:
2449:
2447:
2443:
2437:
2434:
2432:
2429:
2427:
2424:
2422:
2419:
2417:
2413:
2412:
2408:
2405:
2403:
2399:
2396:
2394:
2390:
2389:
2386:
2383:
2381:
2378:
2376:
2373:
2370:
2366:
2363:
2361:
2358:
2356:
2353:
2351:
2347:
2346:
2343:
2340:
2338:
2337:Prednimustine
2335:
2332:
2328:
2325:
2323:
2320:
2317:
2314:
2312:
2308:
2305:
2303:
2300:
2298:
2295:
2293:
2289:
2288:
2286:
2284:
2280:
2277:
2274:
2269:
2265:
2255:
2252:
2250:
2247:
2245:
2242:
2240:
2237:
2234:
2231:
2229:
2226:
2224:
2220:
2219:
2215:
2212:
2209:
2207:
2204:
2202:
2199:
2197:
2194:
2192:
2189:
2187:
2184:
2181:
2177:
2174:
2172:
2169:
2167:
2163:
2162:
2158:
2157:
2155:
2153:
2152:Intercalation
2149:
2145:
2138:
2135:
2133:
2129:
2128:
2124:
2123:
2121:
2119:
2115:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2058:
2054:
2053:
2049:
2048:
2046:
2044:
2040:
2037:
2034:
2029:
2025:
2014:
2010:
2009:
2005:
2004:
2002:
2000:
1996:
1989:
1986:
1984:
1980:
1979:
1975:
1974:
1970:
1966:
1965:
1961:
1960:
1956:
1955:+daunorubicin
1953:
1949:
1948:
1944:
1943:
1939:
1935:
1932:
1930:
1927:
1925:
1922:
1920:
1919:Doxifluridine
1917:
1915:
1912:
1910:
1906:
1905:
1901:
1900:
1898:
1896:
1892:
1885:
1882:
1880:
1876:
1875:
1871:
1869:
1868:Rabacfosadine
1866:
1864:
1861:
1858:
1855:
1853:
1850:
1848:
1844:
1843:
1839:
1835:
1834:
1830:
1826:
1825:
1821:
1820:
1818:
1816:
1812:
1805:
1802:
1800:
1796:
1795:
1791:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1769:
1768:
1764:
1763:
1761:
1759:
1755:
1752:
1749:
1744:
1738:
1735:
1731:
1727:
1716:
1712:
1711:
1707:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1675:
1674:
1670:
1669:
1667:
1663:
1656:
1653:
1651:
1648:
1646:
1643:
1641:
1638:
1636:
1632:
1631:
1627:
1626:
1624:
1621:
1616:
1613:
1610:
1605:
1601:
1597:
1592:
1588:
1584:
1576:
1571:
1569:
1564:
1562:
1557:
1556:
1553:
1533:
1531:
1526:
1520:
1518:
1509:
1505:
1501:
1497:
1493:
1489:
1482:
1474:
1470:
1467:: 1223–1230.
1466:
1459:
1451:
1447:
1443:
1436:
1420:
1414:
1398:
1392:
1385:
1384:public domain
1366:
1364:
1358:
1352:
1336:
1334:
1328:
1322:
1314:
1312:9780857113382
1308:
1304:
1298:
1289:
1284:
1280:
1276:
1270:
1255:
1251:
1245:
1229:
1225:
1219:
1217:
1215:
1213:
1211:
1209:
1207:
1205:
1203:
1185:
1183:
1178:
1172:
1170:
1168:
1166:
1164:
1157:
1152:
1136:
1132:
1126:
1124:
1122:
1105:
1101:
1095:
1093:
1076:
1072:
1066:
1051:
1047:
1043:
1037:
1033:
1025:
1023:
1019:
1004:
1002:
998:
994:
990:
986:
982:
978:
974:
970:
966:
965:phenylalanine
958:
953:
947:
941:
932:
930:
926:
925:RNA synthesis
922:
921:DNA synthesis
918:
914:
910:
898:
895:
892:
890:
887:
885:
882:
880:
877:
875:
872:
869:
866:
864:
860:
859:
858:
850:
847:
845:
841:
838:
837:
835:
832:
830:
827:
826:
825:
817:
813:
811:
807:
803:
798:
795:
785:
783:
779:
774:
772:
768:
764:
761:
757:
753:
749:
744:
742:
738:
734:
730:
726:
722:
721:neuroblastoma
718:
714:
710:
706:
702:
698:
688:
681:
672:
667:
666:
663:
656:
647:
646:
643:
636:
629:
625:
624:
622:
619:
614:
607:
605:
601:
568:
566:
562:
557:
553:
549:
546:
544:
542:ECHA InfoCard
538:
530:
526:
525:DTXSID6020804
522:
521:
519:
510:
506:
499:
495:
494:
492:
490:
486:
479:
475:
474:
472:
470:
466:
459:
455:
454:
452:
450:
446:
439:
435:
434:
432:
430:
426:
419:
415:
414:
412:
410:
406:
399:
395:
394:
392:
390:
386:
379:
375:
374:
372:
370:
366:
359:
355:
354:
352:
345:
341:
334:
330:
329:
327:
325:
321:
308:
307:
304:
297:
292:
288:
285:
283:
279:
275:
273:
266:
262:
260:
256:
252:
250:
246:
242:
238:
232: Rx-only
225:
222:
210:
207:
197:
196:
194:
192:
188:
183:
175:
170:
167:
166:
164:
162:
158:
155:
151:
147:
144:
142:
136:
129:
124:
115:
114:
112:
110:
106:
102:
98:
96:
92:
88:
84:
82:
78:
74:
69:
64:
60:
56:
54:
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
3575:Orphan drugs
3418:Spiromustine
3397:
3393:Mannomustine
3383:Chlorambucil
3378:Bendamustine
3166:Tazemetostat
3130:Alitretinoin
3123:
3049:Estramustine
3029:Elsamitrucin
3019:Eflornithine
2973:Pegaspargase
2969:Asparaginase
2962:
2931:Testolactone
2924:
2912:
2900:
2854:
2839:Panobinostat
2822:
2792:
2780:
2768:
2756:
2727:
2692:
2680:
2633:
2629:Padeliporfin
2568:Dactinomycin
2564:Streptomyces
2545:Temozolomide
2540:Mitozolomide
2528:
2519:Mitobronitol
2508:Procarbazine
2501:
2489:Nonclassical
2414:
2391:
2385:Streptozocin
2350:Nitrosoureas
2348:
2326:
2322:Chlorambucil
2316:Trofosfamide
2302:Chlormethine
2297:Bendamustine
2290:
2228:Mitoxantrone
2223:Losoxantrone
2216:
2176:Daunorubicin
2159:
2125:
2062:Camptothecin
2050:
2006:
1976:
1962:
1945:
1929:Fluorouracil
1909:Capecitabine
1902:
1872:
1836:
1822:
1792:
1787:Pralatrexate
1777:Methotrexate
1765:
1708:
1671:
1628:
1538:21 September
1536:. Retrieved
1528:
1491:
1487:
1481:
1464:
1458:
1441:
1435:
1423:. Retrieved
1413:
1401:. Retrieved
1391:
1369:. Retrieved
1360:
1351:
1339:. Retrieved
1330:
1321:
1302:
1297:
1288:10665/325771
1278:
1269:
1257:. Retrieved
1253:
1244:
1232:. Retrieved
1227:
1188:. Retrieved
1180:
1151:
1139:. Retrieved
1134:
1108:. Retrieved
1103:
1079:. Retrieved
1074:
1065:
1053:. Retrieved
1045:
1036:
1015:
1012:Legal status
1000:
984:
968:
962:
929:cytotoxicity
906:
856:
823:
820:Side effects
814:
802:conditioning
799:
791:
788:Medical uses
775:
745:
719:; childhood
700:
696:
695:
684:
269:Elimination
191:Legal status
185:Legal status
109:License data
67:
18:
3428:Neurotoxins
3241:from market
3211:Vorasidenib
3191:Trabectedin
3176:Tiazofurine
3171:Tebentafusp
3156:Tagraxofusp
3119:Plitidepsin
3094:Mitoguazone
3039:Epacadostat
3009:Demecolcine
2953:Aflibercept
2926:Sex steroid
2799:Fuzuloparib
2740:Carfilzomib
2712:Palbociclib
2702:Abemaciclib
2655:Verteporfin
2619:Efaproxiral
2535:Dacarbazine
2497:Altretamine
2479:Satraplatin
2474:Oxaliplatin
2454:Carboplatin
2431:Triaziquone
2402:Mannosulfan
2380:Ranimustine
2360:Fotemustine
2201:Pirarubicin
2186:Doxorubicin
2180:+cytarabine
2166:Aclarubicin
2127:Podophyllum
2052:Camptotheca
1983:Azacitidine
1969:Gemcitabine
1924:Floxuridine
1857:Fludarabine
1852:Clofarabine
1838:Halogenated
1829:Pentostatin
1804:Raltitrexed
1772:Aminopterin
1715:Ixabepilone
1710:Epothilones
1678:Cabazitaxel
1655:Vinorelbine
1640:Vincristine
1635:Vinblastine
1620:microtubule
1419:"Melphalan"
1403:7 September
1371:7 September
1341:7 September
973:phthalimide
943:Syntheses:
911:nucleotide
834:Bone marrow
752:anaphylaxis
611: g·mol
548:100.005.207
478:CHEBI:28876
294:Identifiers
150:intravenous
95:MedlinePlus
62:Other names
53:Trade names
3544:Categories
3497:Dibenamine
3206:Verdinexor
3201:Venetoclax
3109:Oblimersen
3104:Navitoclax
3084:Lucanthone
3079:Lonidamine
3074:Lifileucel
3069:Ivosidenib
3064:Imetelstat
3034:Enasidenib
3024:Elesclomol
2989:Bexarotene
2984:Belzutifan
2919:Bexarotene
2907:Atrasentan
2882:Umbralisib
2877:Idelalisib
2867:Copanlisib
2849:Vorinostat
2844:Romidepsin
2834:Entinostat
2829:Belinostat
2787:Masoprocol
2775:Tiazofurin
2763:Anagrelide
2735:Bortezomib
2722:Seliciclib
2717:Ribociclib
2697:inhibitors
2687:Tipifarnib
2650:Temoporfin
2645:Talaporfin
2583:Plicamycin
2578:Mitomycins
2524:Pipobroman
2503:Hydrazines
2469:Nedaplatin
2421:Carboquone
2416:Aziridines
2407:Treosulfan
2355:Carmustine
2342:Uramustine
2311:Ifosfamide
2283:Alkylating
2244:Bisantrene
2233:Pixantrone
2206:Valrubicin
2196:Idarubicin
2191:Epirubicin
2137:Teniposide
2092:Lurtotecan
2087:Irinotecan
1988:Decitabine
1952:Cytarabine
1895:Pyrimidine
1884:Tioguanine
1874:Thiopurine
1863:Nelarabine
1847:Cladribine
1799:Pemetrexed
1782:Pemetrexed
1758:Folic acid
1698:Paclitaxel
1650:Vinflunine
1055:22 October
1028:References
963:4-Nitro-L-
917:alkylation
727:; mammary
616:3D model (
604:Molar mass
438:Q41OR9510P
409:ChemSpider
369:IUPHAR/BPS
324:CAS Number
303:IUPAC name
259:Metabolism
3403:Mustamine
3398:Melphalan
3307:Vesicants
3251:Phase III
3239:Withdrawn
3216:Vosaroxin
3196:Veliparib
3151:Sotorasib
3141:Selinexor
3135:Tretinoin
3125:Retinoids
3054:Glasdegib
2999:Celecoxib
2948:Adagrasib
2872:Duvelisib
2862:Alpelisib
2817:Rucaparib
2804:Niraparib
2745:Oprozomib
2707:Alvocidib
2573:Bleomycin
2530:Triazenes
2514:Etoglucid
2459:Cisplatin
2375:Nimustine
2369:Semustine
2365:Lomustine
2327:Melphalan
2254:Menogaril
2249:Crisnatol
2239:Amsacrine
2211:Zorubicin
2171:Amrubicin
2132:Etoposide
2107:Topotecan
2102:Silatecan
2097:Rubitecan
2082:Gimatecan
2067:Cositecan
2057:Belotecan
1733:inhibitor
1703:Tesetaxel
1693:Ortataxel
1688:Larotaxel
1683:Docetaxel
1645:Vindesine
1259:9 October
1254:Drugs.com
1234:9 October
1228:Drugs.com
935:Synthesis
874:Hair loss
844:infection
794:indicated
697:Melphalan
498:ChEMBL852
282:Excretion
271:half-life
139:Routes of
128:Melphalan
87:Monograph
81:Drugs.com
23:Melphalan
3534:Medicine
3099:Mitotane
3044:Eribulin
2812:Olaparib
2750:Ixazomib
2426:Thiotepa
2398:Busulfan
2077:Exatecan
1914:Carmofur
1622:assembly
1585: /
1508:13243678
1444:: 2409.
1425:4 August
1277:(2019).
1190:23 April
1141:23 April
1135:DailyMed
1110:23 April
1104:DailyMed
1081:30 March
915:through
737:by mouth
687:(verify)
389:DrugBank
333:148-82-3
161:ATC code
146:By mouth
123:DailyMed
2033:S phase
1934:Tegafur
1748:S phase
1673:Taxanes
1609:M phase
989:oxirane
913:guanine
889:Itching
861:Severe
756:cancers
701:Alkeran
565:Formula
398:DB01042
344:PubChem
223:Rx-only
220:WARNING
177:)
171: (
169:L01AA03
125::
101:a682220
3520:Portal
3355:TL-995
3350:TL-695
3345:TL-513
3340:TL-512
3335:TL-481
3330:TL-301
3234:WHO-EM
2858:(Pi3K)
1815:Purine
1618:Block
1506:
1488:Lancet
1309:
829:Nausea
739:or by
731:; and
642:SMILES
609:305.20
489:ChEMBL
458:D00369
418:405297
358:460612
287:Kidney
217:
204:
121:
3507:SY-28
3490:Other
3466:DSP-4
2770:IMPDI
2665:Other
1532:(EMA)
1365:(FDA)
1361:U.S.
1335:(FDA)
1331:U.S.
1184:(EMA)
981:ester
662:InChI
618:JSmol
469:ChEBI
3461:DMEA
2856:PIKI
2824:HDAC
2273:CCNS
1540:2020
1504:PMID
1427:2014
1405:2023
1373:2023
1343:2023
1307:ISBN
1261:2019
1236:2019
1192:2022
1143:2022
1112:2022
1083:2024
1057:2023
957:NRDC
923:and
884:Rash
769:and
449:KEGG
429:UNII
378:7620
243:data
77:AHFS
3325:HN3
3320:HN2
3315:HN1
2902:ERA
2758:PhI
2729:PrI
2694:CDK
2606:PDT
1604:MIs
1600:SPs
1591:L01
1496:doi
1492:266
1469:doi
1446:doi
1283:hdl
1050:FDA
1003:).
909:DNA
771:RNA
767:DNA
514:EPA
348:CID
310:4--
174:WHO
3546::
3247::
2782:LI
2682:FI
2148:II
2118:II
1940:))
1527:.
1516:^
1502:.
1490:.
1359:.
1329:.
1252:.
1226:.
1201:^
1179:.
1162:^
1133:.
1120:^
1102:.
1091:^
1073:.
1048:.
1044:.
959:).
949:;
784:.
773:.
743:.
723:;
711:;
582:Cl
579:18
573:13
228:EU
213:US
206:S4
200:AU
152:,
148:,
118:US
66:(2
3522::
3291:e
3284:t
3277:v
3137:)
3128:(
2975:)
2971:/
2967:(
2933:)
2929:(
2921:)
2917:(
2909:)
2905:(
2884:)
2860:(
2851:)
2827:(
2819:)
2797:(
2789:)
2785:(
2777:)
2773:(
2765:)
2761:(
2724:)
2700:(
2689:)
2685:(
2657:)
2638:(
2604:/
2585:)
2566:(
2547:)
2533:(
2510:)
2506:(
2418::
2409:)
2400:(
2395::
2371:)
2367:(
2352::
2333:)
2329:(
2318:)
2309:(
2294::
2275:)
2271:(
2235:)
2221:(
2213:)
2182:)
2178:(
2164:(
2150:+
2139:)
2130:(
2109:)
2055:(
2043:I
2035:)
2031:(
2015:)
2011:(
1990:)
1981:(
1971:)
1967:(
1957:)
1950:(
1936:(
1907:(
1886:)
1877:(
1859:)
1845:(
1840:/
1831:)
1827:(
1806:)
1797:(
1789:)
1770:(
1750:)
1746:(
1717:)
1713:(
1705:)
1676:(
1657:)
1633:(
1611:)
1607:(
1602:/
1593:)
1589:(
1574:e
1567:t
1560:v
1542:.
1510:.
1498::
1475:.
1471::
1452:.
1448::
1429:.
1386:.
1375:.
1345:.
1315:.
1285::
1263:.
1238:.
1194:.
1145:.
1114:.
1085:.
1059:.
1001:3
985:2
983:(
969:1
967:(
620:)
597:2
594:O
591:2
588:N
585:2
576:H
570:C
516:)
512:(
312:L
230::
215::
202::
79:/
68:S
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
