1052:, where the amine group is converted to an imine by deprotonation, then attacks the free aldehyde to form a carbocation that is quenched by electrons from the methyl-phenol ring. This is done in the EtuA2 T-domain. This reaction is done a second time to yield a dimer of modified tyrosine residues that have been further cyclized via Pictet-Spengler reaction, yielding a bicyclic ring moiety. The EtuO and EtuF3 enzymes continue to post-translationally modify the molecule, adding several functional groups and making a sulfide bridge between the original cysteine residue and the beta-carbon of the first tyrosine to form ET-583, ET-597, ET-596, and ET-594 which have been previously isolated. A third
702:
679:
1030:
42:
960:. However, the pivotal study did show a significant difference between two different trabectedin treatment regimens, and due to the rarity of the disease, the CHMP considered that marketing authorization could be granted under exceptional circumstances. As part of the approval PharmaMar agreed to conduct a further trial to identify whether any specific chromosomal
3691:
774:
1457:
912:
licensed the compound from the
University of Illinois before 1994 and attempted to farm the sea squirt with limited success. Yields from the sea squirt are extremely low as around 1,000 kilograms of animals is needed to isolate 1 gram of trabectedin - and about 5 grams were believed to be
903:
was found to have anticancer activity in 1969. Separation and characterization of the active molecules had to wait many years for the development of sufficiently sensitive techniques, and the structure of one of them, Ecteinascidin 743, was determined by KL Rinehart at the
University of Illinois in
917:
to search for a synthetic method of preparation. His group developed such a method and published it in 1996. This was later followed by a simpler and more tractable method which was patented by
Harvard and subsequently licensed to PharmaMar. The current supply is based on a semisynthetic process
1132:
work that this binding occurs in the minor groove, spans approximately three to five base pairs and is most efficient with CGG sequences. Additional favorable binding sequences are TGG, AGC, or GGC. Once bound, this reversible covalent adduct bends DNA toward the major groove, interferes directly
1047:
starts with a fatty acid loading onto the acyl-ligase domain of the EtuA3 module. A cysteine and glycine are then loaded as canonical NRPS amino acids. A tyrosine residue is modified by the enzymes EtuH, EtuM1, and EtuM2 to add a hydroxyl at the meta position of the phenol, and adding two methyl
816:
InChI=1S/C39H43N3O11S/c1-16-9-20-10-22-37(46)42-23-13-50-38(47)39(21-12-25(48-5)24(44)11-19(21)7-8-40-39)14-54-36(30(42)29(41(22)4)26(20)31(45)32(16)49-6)28-27(23)35-34(51-15-52-35)17(2)33(28)53-18(3)43/h9,11-12,22-23,29-30,36-37,40,44-46H,7-8,10,13-15H2,1-6H3/t22-,23-,29+,30+,36+,37-,39+/m0/s1
952:(CHMP), observed that trabectedin had not been evaluated in an adequately designed and analyzed randomized controlled trial against current best care, and that the clinical efficacy data were mainly based on patients with
1127:
Other than transcriptional interference, the mechanism of action of trabectedin is complex and not completely understood. The compound is known to bind and alkylate DNA at the N2 position of guanine. It is known from
1876:
Son K, Takhaveev V, Mor V, Yu H, Dillier E, Zilio N, et al. (February 2024). "Trabectedin derails transcription-coupled nucleotide excision repair to induce DNA breaks in highly transcribed genes".
978:
approved trabectedin (Yondelis) for the treatment of liposarcoma and leiomyosarcoma that is either unresectable or has metastasized. Patients must have received prior chemotherapy with an anthracycline.
940:
In 2007, the
European Commission gave authorization for the marketing of trabectedin, under the trade name Yondelis, "for the treatment of patients with advanced soft tissue sarcoma, after failure of
1458:"Hostages of the deep - Prospectors are taking to the seas in search of new and promising chemicals. But the better the drugs turn out to be, the greater the threat to the animals that produce them"
999:. In 2011, Johnson & Johnson voluntarily withdrew the submission in the United States following a request by the FDA for an additional phase III study to be done in support of the submission.
300:
904:
1984. Rinehart had collected his sea squirts by scuba diving in the reefs of the West Indies. The biosynthetic pathway responsible for producing the drug has been determined to come from
1505:
Cuevas C, Pérez M, Martín MJ, Chicharro JL, Fernández-Rivas C, Flores M, et al. (August 2000). "Synthesis of ecteinascidin ET-743 and phthalascidin Pt-650 from cyanosafracin B".
870:
It is sold by Pharma Mar S.A. and
Johnson and Johnson. It is approved for use in the European Union, Russia, South Korea and the United States. The European Commission and the U.S.
1652:
1105:
to assist in the formation of the pentacyclic core. This reaction was unprecedented for using such a one pot multicomponent reaction in the synthesis of such a complex molecule.
255:
832:
1630:
1145:
1969:
1685:
1149:
1134:
3731:
1124:. By reversing the genetic program created by this transcription factor, trabectedin promotes differentiation and reverses the oncogenic phenotype in these cells.
949:
1540:
1586:
136:
2669:
788:
867:
The most common adverse reactions include nausea, fatigue, vomiting, constipation, decreased appetite, diarrhea, peripheral edema, dyspnea, and headache.
187:
1569:
3711:
3645:
1962:
1789:
1312:
Lichter W, Wallham LL, Van Der Worf BA, Middle Brook RE, Sigal MM, Weinheimer AJ (August 1972). Worthen LW (ed.). "Food Drugs from the Sea".
1380:
3252:
2404:
2360:
2238:
1660:
1409:"Meta-omic characterization of the marine invertebrate microbial consortium that produces the chemotherapeutic natural product ET-743"
1173:
In
September 2020, the European Medicines Agency recommended that the use of trabectedin in treating ovarian cancer remain unchanged.
3751:
2163:
808:
104:
1638:
1344:
1955:
1250:
1160:
incision at trabectedin lesions, recording TC-NER on a genome-wide scale, which resulted in a TC-NER-profiling assay TRABI-Seq.
2885:
2679:
424:
285:
168:
1707:
1675:
1152:
of trabectedin-DNA adducts forms persistent single-strand breaks (SSBs) as the adducts block the second of the two sequential
894:
carried out a wide-ranging program of screening plant and marine organism material. As part of that program, extract from the
3298:
2300:
2190:
460:)-6',8,14-trihydroxy-7',9-dimethoxy-4,10,23-trimethyl-19-oxo-3',4',6,7,12,13,14,16-octahydrospiroisoquinobenzazocine-20,1'(2'
1068:
by E.J. Corey used this proposed biosynthesis to guide their synthetic strategy. The synthesis uses such reactions as the
3721:
3220:
3203:
3078:
2842:
2220:
1048:
groups at the para-hydroxyl and the meta carbon position. This modified tyrosine reacts with the original substrate via a
3681:
3756:
2952:
2548:
871:
578:
204:
3662:
3154:
1947:
658:
1590:
2334:
1157:
1153:
3520:
3400:
3390:
1927:
1288:
988:
891:
182:
3746:
3572:
3505:
3475:
3093:
2343:
1073:
1049:
527:
3716:
3650:
3557:
3375:
3090:
2576:
2424:
2351:
1220:"Yondelis 1 mg powder for concentrate for solution for infusion - Summary of Product Characteristics (SmPC)"
920:
899:
241:
1729:
D'Incalci M, Galmarini CM (August 2010). "A review of trabectedin (ET-743): a unique mechanism of action".
697:
3726:
3455:
3445:
3178:
3020:
1680:
1011:
366:
948:, or who are unsuited to receive these agents". The European Medicine Agency's evaluating committee, the
924:. PharmaMar entered into an agreement with Johnson & Johnson to market the compound outside Europe.
647:
3736:
2727:
2544:
2514:
2374:
1081:
1077:
518:
918:
developed by PharmaMar starting from safracin B, a chemical obtained by fermentation of the bacterium
3125:
3002:
2523:
2439:
1114:
393:
3410:
3310:
3289:
3010:
2832:
2664:
2395:
2291:
1604:
857:
674:
473:
248:
1922:
2468:
1754:
1356:
1121:
215:
3617:
2498:
2478:
2463:
1388:
3592:
3166:
2000:
1904:
1857:
1805:
1785:
1746:
1522:
1438:
1348:
914:
627:
326:
313:
118:
1283:
796:
Cc1cc2c(c(c1OC)O)345c6c(c7c(c(c6OC(=O)C)C)OCO7)(N4((C2)N3C)O)COC(=O)8(CS5)c9cc(c(cc9CCN8)O)OC
3741:
3597:
3354:
3069:
2703:
2688:
2409:
1894:
1886:
1847:
1839:
1795:
1777:
1738:
1514:
1487:
1478:
Corey EJ, Gin DY, Kania RS (1996). "Enantioselective Total
Synthesis of Ecteinascidin 743".
1428:
1420:
1340:
1156:
incisions. The researchers mapped the 3’-hydroxyl groups of SSBs originating from the first
1137:
complex, promotes degradation of RNA polymerase II, and generates DNA double-strand breaks.
1095:
1069:
1014:
714:
482:
348:
59:
1826:
Grohar PJ, Griffin LB, Yeung C, Chen QR, Pommier Y, Khanna C, et al. (February 2011).
1056:-methylated tyrosine is added and cyclized via Pictet-Spengler to yield the final product.
587:
567:
3695:
3036:
2998:
2789:
2211:
2126:
1065:
1029:
908:
Endoecteinascidia frumentensis, a microbial symbiont of the tunicate. The
Spanish company
376:
356:
1772:
Chukwueke UN, Wen PY (2020). "Medical management of meningiomas". In McDermott MW (ed.).
701:
678:
3656:
3190:
2781:
2275:
2139:
2026:
1996:
1983:
1852:
1827:
1800:
1781:
1433:
1408:
996:
961:
957:
879:
861:
1219:
41:
3705:
3530:
3490:
2860:
2733:
2614:
2557:
2315:
2264:
1098:
1002:
Trabectedin is also in phase II trials for prostate, breast, and paediatric cancers.
941:
690:
160:
1360:
3577:
3541:
3425:
3415:
3369:
3365:
3327:
3235:
3025:
2964:
2960:
2941:
2936:
2915:
2904:
2718:
2712:
2698:
2693:
2624:
2619:
2572:
2458:
2325:
2305:
2234:
2183:
2173:
1987:
1979:
1828:"Ecteinascidin 743 interferes with the activity of EWS-FLI1 in Ewing sarcoma cells"
1758:
1715:
1102:
1088:
507:
268:
263:
146:
1742:
1407:
Rath CM, Janto B, Earl J, Ahmed A, Hu FZ, Hiller L, et al. (November 2011).
1113:
Recently, it has been shown that trabectedin blocks DNA binding of the oncogenic
3622:
3587:
3582:
3567:
3525:
3495:
3435:
3405:
3349:
3322:
3195:
3136:
3108:
3098:
3051:
3015:
2931:
2893:
2875:
2870:
2850:
2827:
2798:
2776:
2756:
2746:
2597:
2582:
2562:
2448:
2379:
2365:
2320:
2253:
2248:
2225:
2200:
2168:
2111:
2074:
2051:
2036:
2031:
2016:
992:
971:
953:
875:
154:
1899:
1890:
3612:
3515:
3510:
3485:
3480:
3470:
3465:
3460:
3430:
3420:
3385:
3380:
3360:
3315:
3303:
3278:
3273:
3263:
3245:
3240:
3230:
3225:
3183:
3171:
3159:
3131:
3118:
3113:
3083:
3046:
3041:
2979:
2974:
2920:
2865:
2817:
2803:
2751:
2738:
2707:
2640:
2629:
2602:
2592:
2587:
2533:
2488:
2483:
2384:
2348:
2280:
2270:
2259:
2243:
2195:
2178:
2154:
2106:
2094:
2046:
1193:
1141:
945:
750:
558:
1776:. Handbook of Clinical Neurology. Vol. 170. Elsevier. pp. 291–302.
3627:
3607:
3562:
3552:
3546:
3450:
3395:
3344:
3268:
3258:
3213:
3200:
3141:
3103:
3031:
2969:
2910:
2899:
2855:
2812:
2771:
2765:
2761:
2723:
2650:
2645:
2635:
2607:
2567:
2528:
2503:
2493:
2453:
2099:
2089:
2084:
2079:
2041:
1092:
1038:
909:
406:
140:
33:
1908:
1861:
1809:
1750:
1526:
1442:
1352:
3536:
3500:
3440:
3208:
3146:
2926:
2822:
2794:
2473:
2310:
1117:
1018:
895:
538:
199:
856:, is an antitumor chemotherapy medication for the treatment of advanced
547:
17:
2429:
2330:
2144:
2005:
1843:
1084:
1017:, eight rings including one 10-membered heterocyclic ring containing a
987:
In 2008, the submission was announced of a registration dossier to the
493:
1653:"FDA Approves Trabectedin (Yondelis) for Advanced Soft-Tissue Sarcoma"
1518:
1491:
1424:
1345:
10.1002/(SICI)1098-1128(200001)20:1<1::AID-MED1>3.0.CO;2-A
2069:
1631:"Trabectedin Superior to Dacarbazine for Leiomyosarcoma, Liposarcoma"
975:
638:
385:
1251:"Yondelis- trabectedin injection, powder, lyophilized, for solution"
607:
1331:
Rinehart KL (January 2000). "Antitumor compounds from tunicates".
1028:
913:
needed for a clinical trial so
Rinehart asked the Harvard chemist
773:
764:
618:
381:
598:
332:
307:
186:
177:
1951:
991:
and the FDA for
Yondelis when administered in combination with
320:
194:
970:
In 2015, (after a phase III study comparing trabectedin with
663:
294:
226:
77:
68:
995:(Doxil, Caelyx) for the treatment of women with relapsed
92:
86:
1381:"Potent cancer drugs made -- Sea squirts provide recipe"
967:
Trabectedin is also approved in South Korea and Russia.
964:
could be used to predict responsiveness to trabectedin.
839:
1188:
1186:
3679:
105:
95:
80:
1245:
1243:
1241:
89:
83:
74:
65:
62:
3337:
3288:
3068:
3061:
2997:
2951:
2884:
2841:
2678:
2663:
2543:
2513:
2438:
2423:
2394:
2290:
2210:
2153:
2136:
2125:
2061:
2014:
1995:
878:status to trabectedin for soft-tissue sarcomas and
762:
749:
713:
708:
689:
657:
637:
617:
597:
577:
557:
537:
526:
517:
492:
472:
415:
405:
392:
375:
365:
355:
347:
284:
279:
254:
240:
214:
167:
153:
135:
127:
117:
71:
53:
48:
1101:. A separate synthetic process also involved the
932:Trabectedin was first trialed in humans in 1996.
1676:"J&J pulls submission for Zeltia's Yondelis"
1150:transcription-coupled nucleotide excision repair
1135:transcription-coupled nucleotide excision repair
1037:The biosynthesis of trabectedin in the tunicate
1033:Proposed scheme for the biosynthesis of the drug
506:
1278:
1276:
1274:
1272:
481:
1605:"S.Korea approves Zeltia cancer drug Yondelis"
1550:. European Medicines Agency. 24 September 2009
1548:Post-Authorization Summary of Positive Opinion
1402:
1400:
1398:
950:Committee for Medicinal Products for Human Use
1963:
1821:
1819:
8:
1120:and reverses the transcriptional program in
203:
32:
340:In general: ℞ (Prescription only)
3065:
2675:
2435:
2150:
2133:
2011:
1970:
1956:
1948:
1133:with activated transcription, poisons the
700:
677:
566:
40:
1898:
1851:
1799:
1432:
1374:
1372:
1370:
586:
3732:Drugs developed by Johnson & Johnson
1480:Journal of the American Chemical Society
1473:
1471:
3686:
1684:. London, England. Online PharmaTimes.
1182:
813:
793:
673:
546:
429:
159:
1198:Therapeutic Goods Administration (TGA)
691:
31:
646:
626:
145:
7:
267:
2239:ribonucleotide reductase inhibitors
1688:from the original on 2 October 2011
1637:. 21 September 2015. Archived from
1021:residue, and seven chiral centers.
606:
497:
2405:Ribonucleotide reductase inhibitor
2361:Ribonucleotide reductase inhibitor
1782:10.1016/B978-0-12-822198-3.00048-3
25:
2164:Dihydrofolate reductase inhibitor
1659:. 26 October 2015. Archived from
1010:Trabectedin is composed of three
3689:
890:During the 1950s and 1960s, the
731:
725:
58:
993:pegylated liposomal doxorubicin
821:Key:PKVRCIRHQMSYJX-AIFWHQITSA-N
2301:Thymidylate synthase inhibitor
2191:Thymidylate synthase inhibitor
1045:Endoecteinascidia frumentensis
743:
737:
719:
1:
2221:Adenosine deaminase inhibitor
2062:Block microtubule disassembly
1743:10.1158/1535-7163.MCT-10-0263
1731:Molecular Cancer Therapeutics
3712:2,5-Dimethoxyphenethylamines
1456:Pain S (14 September 1996).
872:Food and Drug Administration
852:, sold under the brand name
1320:. Marine Tech Soc: 117–127.
464:)-isoquinolin]-5-yl acetate
3773:
1891:10.1038/s41467-024-45664-7
1385:Harvard University Gazette
1333:Medicinal Research Reviews
1140:In 2024, researchers from
709:Chemical and physical data
3640:
3521:Omacetaxine mepesuccinate
3401:Ciltacabtagene autoleucel
3391:Brexucabtagene autoleucel
1928:European Medicines Agency
1289:European Medicines Agency
1148:determined that abortive
989:European Medicines Agency
928:Approvals and indications
892:National Cancer Institute
829:
804:
784:
420:
131:ecteinascidin 743, ET-743
39:
3752:Phenethylamine alkaloids
3573:Talimogene laherparepvec
3506:Nadofaragene firadenovec
3476:Lisocabtagene maraleucel
2425:Topoisomerase inhibitors
2344:DNA polymerase inhibitor
1866:and works cited therein.
1708:"Yondelis (trabectedin)"
1541:"YONDELIS (trabectedin)"
1379:Cromie WJ (4 May 2000).
1074:Pictet-Spengler reaction
1050:Pictet-Spengler reaction
983:Ovarian cancer and other
886:Discovery and production
361:Not applicable (IV only)
3376:Axicabtagene ciloleucel
1980:chemotherapeutic agents
1674:Grogan K (3 May 2011).
921:Pseudomonas fluorescens
900:Ecteinascidia turbinata
3558:Sitimagene ceradenovec
3456:Idecabtagene vicleucel
3021:Methyl aminolevulinate
1593:on September 18, 2008.
1034:
1012:tetrahydroisoquinoline
3032:Porphyrin derivatives
2728:Melphalan flufenamide
2375:Hypomethylating agent
1984:antineoplastic agents
1879:Nature Communications
1078:Curtius rearrangement
1032:
3722:Antineoplastic drugs
3361:Asparagine depleters
3290:Receptor antagonists
3204:+abiraterone acetate
1774:Meningiomas, Part II
1718:on 13 February 2012.
1681:PharmaTimes Magazine
1413:ACS Chemical Biology
1115:transcription factor
3757:Bacterial alkaloids
3411:Denileukin diftitox
3311:Retinoid X receptor
3011:Aminolevulinic acid
2833:Triethylenemelamine
2665:Crosslinking of DNA
2396:Deoxyribonucleotide
2335:+gimeracil/oteracil
1900:20.500.11850/661709
1587:"PharmaMar website"
1293:. 17 September 2018
1257:. 22 September 2020
1226:. 21 September 2020
1164:Society and culture
1109:Mechanism of action
936:Soft tissue sarcoma
858:soft-tissue sarcoma
316:(Prescription only)
303:(Prescription only)
36:
3667:Never to phase III
2469:Etirinotecan pegol
1932:. 27 February 2020
1844:10.1593/neo.101202
1122:myxoid liposarcoma
1039:symbiotic bacteria
1035:
3677:
3676:
3636:
3635:
3593:Tigilanol tiglate
3070:Enzyme inhibitors
2993:
2992:
2989:
2988:
2689:Nitrogen mustards
2659:
2658:
2419:
2418:
2121:
2120:
1791:978-0-12-822198-3
1663:on 17 March 2016.
1570:"CHMP evaluation"
1519:10.1021/ol0062502
1513:(16): 2545–2548.
1492:10.1021/ja962480t
1486:(38): 9202–9203.
1425:10.1021/cb200244t
1419:(11): 1244–1256.
847:
846:
775:Interactive image
659:CompTox Dashboard
336:
324:
311:
298:
230:
197:
180:
27:Chemical compound
16:(Redirected from
3764:
3694:
3693:
3692:
3685:
3598:Tisagenlecleucel
3355:Arsenic trioxide
3066:
2999:Photosensitizers
2790:Alkyl sulfonates
2704:Cyclophosphamide
2676:
2615:Anthracenediones
2436:
2410:Hydroxycarbamide
2151:
2134:
2012:
1972:
1965:
1958:
1949:
1942:
1941:
1939:
1937:
1919:
1913:
1912:
1902:
1873:
1867:
1865:
1855:
1823:
1814:
1813:
1803:
1769:
1763:
1762:
1737:(8): 2157–2163.
1726:
1720:
1719:
1714:. Archived from
1704:
1698:
1697:
1695:
1693:
1671:
1665:
1664:
1649:
1643:
1642:
1641:on 5 March 2016.
1627:
1621:
1620:
1618:
1616:
1601:
1595:
1594:
1589:. Archived from
1583:
1577:
1576:
1574:
1566:
1560:
1559:
1557:
1555:
1545:
1537:
1531:
1530:
1502:
1496:
1495:
1475:
1466:
1465:
1453:
1447:
1446:
1436:
1404:
1393:
1392:
1387:. Archived from
1376:
1365:
1364:
1328:
1322:
1321:
1309:
1303:
1302:
1300:
1298:
1280:
1267:
1266:
1264:
1262:
1247:
1236:
1235:
1233:
1231:
1216:
1210:
1209:
1207:
1205:
1190:
1096:enantioselective
1070:Mannich reaction
843:
842:
835:
777:
757:
745:
739:
733:
727:
721:
704:
693:
682:
681:
667:
665:
650:
630:
610:
590:
570:
550:
530:
510:
500:
499:
485:
401:180 hours (mean)
397:
334:
331:
322:
319:
309:
306:
296:
293:
271:
228:
225:
207:
196:
193:
190:
179:
176:
163:
149:
109:
102:
101:
98:
97:
94:
91:
88:
85:
82:
79:
76:
73:
70:
67:
64:
44:
37:
35:
21:
3772:
3771:
3767:
3766:
3765:
3763:
3762:
3761:
3747:Total synthesis
3702:
3701:
3700:
3690:
3688:
3680:
3678:
3673:
3672:
3657:Clinical trials
3632:
3338:Other/ungrouped
3333:
3284:
3057:
3037:Porfimer sodium
2985:
2947:
2880:
2837:
2667:
2655:
2539:
2509:
2427:
2415:
2390:
2286:
2206:
2142:
2140:antimetabolites
2138:
2137:DNA precursors/
2129:
2127:DNA replication
2117:
2057:
2027:Vinca alkaloids
2003:
1991:
1976:
1946:
1945:
1935:
1933:
1921:
1920:
1916:
1875:
1874:
1870:
1825:
1824:
1817:
1792:
1771:
1770:
1766:
1728:
1727:
1723:
1706:
1705:
1701:
1691:
1689:
1673:
1672:
1668:
1651:
1650:
1646:
1629:
1628:
1624:
1614:
1612:
1603:
1602:
1598:
1585:
1584:
1580:
1572:
1568:
1567:
1563:
1553:
1551:
1543:
1539:
1538:
1534:
1507:Organic Letters
1504:
1503:
1499:
1477:
1476:
1469:
1455:
1454:
1450:
1406:
1405:
1396:
1391:on 3 June 2006.
1378:
1377:
1368:
1330:
1329:
1325:
1311:
1310:
1306:
1296:
1294:
1284:"Yondelis EPAR"
1282:
1281:
1270:
1260:
1258:
1249:
1248:
1239:
1229:
1227:
1218:
1217:
1213:
1203:
1201:
1192:
1191:
1184:
1179:
1171:
1166:
1111:
1066:total synthesis
1062:
1060:Total synthesis
1027:
1008:
985:
938:
930:
888:
838:
836:
833:(what is this?)
830:
825:
822:
817:
812:
811:
800:
797:
792:
791:
780:
755:
742:
736:
730:
724:
685:
661:
653:
633:
613:
593:
573:
553:
533:
513:
496:
488:
468:
465:
428:
427:
395:
367:Protein binding
357:Bioavailability
349:Pharmacokinetic
343:
275:
243:
236:
217:
210:
107:
103:
61:
57:
28:
23:
22:
15:
12:
11:
5:
3770:
3768:
3760:
3759:
3754:
3749:
3744:
3739:
3734:
3729:
3724:
3719:
3717:Acetate esters
3714:
3704:
3703:
3699:
3698:
3675:
3674:
3671:
3670:
3669:
3668:
3665:
3654:
3648:
3642:
3641:
3638:
3637:
3634:
3633:
3631:
3630:
3625:
3620:
3615:
3610:
3605:
3600:
3595:
3590:
3585:
3580:
3575:
3570:
3565:
3560:
3555:
3550:
3544:
3533:
3528:
3523:
3518:
3513:
3508:
3503:
3498:
3493:
3488:
3483:
3478:
3473:
3468:
3463:
3458:
3453:
3448:
3443:
3438:
3433:
3428:
3423:
3418:
3413:
3408:
3403:
3398:
3393:
3388:
3383:
3378:
3373:
3357:
3352:
3347:
3341:
3339:
3335:
3334:
3332:
3331:
3319:
3307:
3294:
3292:
3286:
3285:
3283:
3282:
3276:
3271:
3266:
3261:
3249:
3243:
3238:
3233:
3228:
3217:
3211:
3206:
3198:
3191:PARP inhibitor
3187:
3175:
3163:
3151:
3150:
3149:
3144:
3139:
3134:
3122:
3116:
3111:
3106:
3101:
3087:
3074:
3072:
3063:
3059:
3058:
3056:
3055:
3049:
3044:
3039:
3028:
3023:
3018:
3013:
3007:
3005:
2995:
2994:
2991:
2990:
2987:
2986:
2984:
2983:
2977:
2972:
2967:
2957:
2955:
2949:
2948:
2946:
2945:
2939:
2934:
2923:
2918:
2913:
2908:
2896:
2890:
2888:
2882:
2881:
2879:
2878:
2873:
2868:
2863:
2858:
2853:
2847:
2845:
2843:Platinum-based
2839:
2838:
2836:
2835:
2830:
2825:
2820:
2808:
2807:
2801:
2785:
2784:
2779:
2774:
2769:
2759:
2754:
2742:
2741:
2736:
2731:
2721:
2716:
2710:
2701:
2696:
2684:
2682:
2673:
2661:
2660:
2657:
2656:
2654:
2653:
2648:
2643:
2638:
2633:
2627:
2622:
2611:
2605:
2600:
2595:
2590:
2585:
2580:
2570:
2565:
2558:Anthracyclines
2553:
2551:
2541:
2540:
2538:
2537:
2531:
2519:
2517:
2511:
2510:
2508:
2507:
2501:
2496:
2491:
2486:
2481:
2476:
2471:
2466:
2461:
2456:
2444:
2442:
2433:
2421:
2420:
2417:
2416:
2414:
2413:
2400:
2398:
2392:
2391:
2389:
2388:
2382:
2370:
2369:
2356:
2355:
2339:
2338:
2328:
2323:
2318:
2313:
2308:
2296:
2294:
2288:
2287:
2285:
2284:
2278:
2276:Mercaptopurine
2267:
2262:
2257:
2251:
2246:
2230:
2229:
2216:
2214:
2208:
2207:
2205:
2204:
2198:
2187:
2181:
2176:
2171:
2159:
2157:
2148:
2131:
2123:
2122:
2119:
2118:
2116:
2115:
2103:
2097:
2092:
2087:
2082:
2077:
2065:
2063:
2059:
2058:
2056:
2055:
2049:
2044:
2039:
2034:
2022:
2020:
2009:
1993:
1992:
1978:Intracellular
1977:
1975:
1974:
1967:
1960:
1952:
1944:
1943:
1914:
1868:
1838:(2): 145–153.
1815:
1790:
1764:
1721:
1699:
1666:
1657:Cancer Network
1644:
1635:Cancer Network
1622:
1596:
1578:
1561:
1532:
1497:
1467:
1448:
1394:
1366:
1323:
1304:
1268:
1237:
1211:
1181:
1180:
1178:
1175:
1170:
1167:
1165:
1162:
1110:
1107:
1061:
1058:
1026:
1023:
1007:
1004:
997:ovarian cancer
984:
981:
962:translocations
958:leiomyosarcoma
942:anthracyclines
937:
934:
929:
926:
887:
884:
880:ovarian cancer
874:(FDA) granted
862:ovarian cancer
845:
844:
827:
826:
824:
823:
820:
818:
815:
807:
806:
805:
802:
801:
799:
798:
795:
787:
786:
785:
782:
781:
779:
778:
770:
768:
760:
759:
753:
747:
746:
740:
734:
728:
722:
717:
711:
710:
706:
705:
695:
687:
686:
684:
683:
670:
668:
655:
654:
652:
651:
643:
641:
635:
634:
632:
631:
623:
621:
615:
614:
612:
611:
603:
601:
595:
594:
592:
591:
583:
581:
575:
574:
572:
571:
563:
561:
555:
554:
552:
551:
543:
541:
535:
534:
532:
531:
523:
521:
515:
514:
512:
511:
503:
501:
490:
489:
487:
486:
478:
476:
470:
469:
467:
466:
431:
423:
422:
421:
418:
417:
413:
412:
409:
403:
402:
399:
390:
389:
379:
373:
372:
369:
363:
362:
359:
353:
352:
345:
344:
342:
341:
338:
329:
317:
304:
290:
288:
282:
281:
277:
276:
274:
273:
260:
258:
252:
251:
246:
244:administration
238:
237:
235:
234:
232:
222:
220:
212:
211:
209:
208:
191:
173:
171:
165:
164:
157:
151:
150:
143:
133:
132:
129:
125:
124:
121:
115:
114:
55:
51:
50:
46:
45:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3769:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3727:Benzodioxoles
3725:
3723:
3720:
3718:
3715:
3713:
3710:
3709:
3707:
3697:
3687:
3683:
3666:
3664:
3661:
3660:
3658:
3655:
3652:
3649:
3647:
3644:
3643:
3639:
3629:
3626:
3624:
3621:
3619:
3616:
3614:
3611:
3609:
3606:
3604:
3601:
3599:
3596:
3594:
3591:
3589:
3586:
3584:
3581:
3579:
3576:
3574:
3571:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3548:
3545:
3543:
3539:
3538:
3534:
3532:
3531:Tabelecleucel
3529:
3527:
3524:
3522:
3519:
3517:
3514:
3512:
3509:
3507:
3504:
3502:
3499:
3497:
3494:
3492:
3491:Lurbinectedin
3489:
3487:
3484:
3482:
3479:
3477:
3474:
3472:
3469:
3467:
3464:
3462:
3459:
3457:
3454:
3452:
3449:
3447:
3444:
3442:
3439:
3437:
3434:
3432:
3429:
3427:
3424:
3422:
3419:
3417:
3414:
3412:
3409:
3407:
3404:
3402:
3399:
3397:
3394:
3392:
3389:
3387:
3384:
3382:
3379:
3377:
3374:
3371:
3367:
3363:
3362:
3358:
3356:
3353:
3351:
3348:
3346:
3343:
3342:
3340:
3336:
3329:
3325:
3324:
3320:
3317:
3313:
3312:
3308:
3305:
3301:
3300:
3296:
3295:
3293:
3291:
3287:
3280:
3277:
3275:
3272:
3270:
3267:
3265:
3262:
3260:
3256:
3254:
3250:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3223:
3222:
3218:
3215:
3212:
3210:
3207:
3205:
3202:
3199:
3197:
3193:
3192:
3188:
3185:
3181:
3180:
3176:
3173:
3169:
3168:
3164:
3161:
3157:
3156:
3152:
3148:
3145:
3143:
3140:
3138:
3135:
3133:
3130:
3129:
3128:
3127:
3123:
3120:
3117:
3115:
3112:
3110:
3107:
3105:
3102:
3100:
3096:
3095:
3092:
3088:
3085:
3081:
3080:
3076:
3075:
3073:
3071:
3067:
3064:
3060:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3034:
3033:
3029:
3027:
3024:
3022:
3019:
3017:
3014:
3012:
3009:
3008:
3006:
3004:
3000:
2996:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2962:
2959:
2958:
2956:
2954:
2953:Intercalation
2950:
2943:
2940:
2938:
2935:
2933:
2929:
2928:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2906:
2902:
2901:
2897:
2895:
2892:
2891:
2889:
2887:
2883:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2861:Dicycloplatin
2859:
2857:
2854:
2852:
2849:
2848:
2846:
2844:
2840:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2810:
2809:
2805:
2802:
2800:
2796:
2793:
2791:
2787:
2786:
2783:
2780:
2778:
2775:
2773:
2770:
2767:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2744:
2743:
2740:
2737:
2735:
2734:Prednimustine
2732:
2729:
2725:
2722:
2720:
2717:
2714:
2711:
2709:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2686:
2685:
2683:
2681:
2677:
2674:
2671:
2666:
2662:
2652:
2649:
2647:
2644:
2642:
2639:
2637:
2634:
2631:
2628:
2626:
2623:
2621:
2617:
2616:
2612:
2609:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2578:
2574:
2571:
2569:
2566:
2564:
2560:
2559:
2555:
2554:
2552:
2550:
2549:Intercalation
2546:
2542:
2535:
2532:
2530:
2526:
2525:
2521:
2520:
2518:
2516:
2512:
2505:
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2480:
2477:
2475:
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2455:
2451:
2450:
2446:
2445:
2443:
2441:
2437:
2434:
2431:
2426:
2422:
2411:
2407:
2406:
2402:
2401:
2399:
2397:
2393:
2386:
2383:
2381:
2377:
2376:
2372:
2371:
2367:
2363:
2362:
2358:
2357:
2353:
2352:+daunorubicin
2350:
2346:
2345:
2341:
2340:
2336:
2332:
2329:
2327:
2324:
2322:
2319:
2317:
2316:Doxifluridine
2314:
2312:
2309:
2307:
2303:
2302:
2298:
2297:
2295:
2293:
2289:
2282:
2279:
2277:
2273:
2272:
2268:
2266:
2265:Rabacfosadine
2263:
2261:
2258:
2255:
2252:
2250:
2247:
2245:
2241:
2240:
2236:
2232:
2231:
2227:
2223:
2222:
2218:
2217:
2215:
2213:
2209:
2202:
2199:
2197:
2193:
2192:
2188:
2185:
2182:
2180:
2177:
2175:
2172:
2170:
2166:
2165:
2161:
2160:
2158:
2156:
2152:
2149:
2146:
2141:
2135:
2132:
2128:
2124:
2113:
2109:
2108:
2104:
2101:
2098:
2096:
2093:
2091:
2088:
2086:
2083:
2081:
2078:
2076:
2072:
2071:
2067:
2066:
2064:
2060:
2053:
2050:
2048:
2045:
2043:
2040:
2038:
2035:
2033:
2029:
2028:
2024:
2023:
2021:
2018:
2013:
2010:
2007:
2002:
1998:
1994:
1989:
1985:
1981:
1973:
1968:
1966:
1961:
1959:
1954:
1953:
1950:
1931:
1929:
1924:
1918:
1915:
1910:
1906:
1901:
1896:
1892:
1888:
1884:
1880:
1872:
1869:
1863:
1859:
1854:
1849:
1845:
1841:
1837:
1833:
1829:
1822:
1820:
1816:
1811:
1807:
1802:
1797:
1793:
1787:
1783:
1779:
1775:
1768:
1765:
1760:
1756:
1752:
1748:
1744:
1740:
1736:
1732:
1725:
1722:
1717:
1713:
1709:
1703:
1700:
1687:
1683:
1682:
1677:
1670:
1667:
1662:
1658:
1654:
1648:
1645:
1640:
1636:
1632:
1626:
1623:
1610:
1606:
1600:
1597:
1592:
1588:
1582:
1579:
1571:
1565:
1562:
1549:
1542:
1536:
1533:
1528:
1524:
1520:
1516:
1512:
1508:
1501:
1498:
1493:
1489:
1485:
1481:
1474:
1472:
1468:
1463:
1462:New Scientist
1459:
1452:
1449:
1444:
1440:
1435:
1430:
1426:
1422:
1418:
1414:
1410:
1403:
1401:
1399:
1395:
1390:
1386:
1382:
1375:
1373:
1371:
1367:
1362:
1358:
1354:
1350:
1346:
1342:
1338:
1334:
1327:
1324:
1319:
1315:
1308:
1305:
1292:
1290:
1285:
1279:
1277:
1275:
1273:
1269:
1256:
1252:
1246:
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350:
346:
339:
337: Rx-only
330:
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318:
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305:
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292:
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100:
56:
54:Pronunciation
52:
49:Clinical data
47:
43:
38:
30:
19:
3737:Orphan drugs
3602:
3578:Tazemetostat
3542:Alitretinoin
3535:
3446:Estramustine
3426:Elsamitrucin
3416:Eflornithine
3370:Pegaspargase
3366:Asparaginase
3359:
3328:Testolactone
3321:
3309:
3297:
3251:
3236:Panobinostat
3219:
3189:
3177:
3165:
3153:
3124:
3089:
3077:
3030:
3026:Padeliporfin
2965:Dactinomycin
2961:Streptomyces
2942:Temozolomide
2937:Mitozolomide
2925:
2916:Mitobronitol
2905:Procarbazine
2898:
2886:Nonclassical
2811:
2788:
2782:Streptozocin
2747:Nitrosoureas
2745:
2719:Chlorambucil
2713:Trofosfamide
2699:Chlormethine
2694:Bendamustine
2687:
2625:Mitoxantrone
2620:Losoxantrone
2613:
2573:Daunorubicin
2556:
2522:
2459:Camptothecin
2447:
2403:
2373:
2359:
2342:
2326:Fluorouracil
2306:Capecitabine
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2269:
2233:
2219:
2189:
2184:Pralatrexate
2174:Methotrexate
2162:
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2068:
2025:
1936:30 September
1934:. Retrieved
1926:
1917:
1882:
1878:
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1711:
1702:
1690:. Retrieved
1679:
1669:
1661:the original
1656:
1647:
1639:the original
1634:
1625:
1615:30 September
1613:. Retrieved
1611:. 8 May 2008
1608:
1599:
1591:the original
1581:
1564:
1552:. Retrieved
1547:
1535:
1510:
1506:
1500:
1483:
1479:
1461:
1451:
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1412:
1389:the original
1384:
1336:
1332:
1326:
1317:
1313:
1307:
1297:30 September
1295:. Retrieved
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1261:30 September
1259:. Retrieved
1254:
1230:30 September
1228:. Retrieved
1223:
1214:
1202:. Retrieved
1200:. 3 May 2021
1197:
1172:
1169:Legal status
1139:
1129:
1126:
1112:
1103:Ugi reaction
1063:
1053:
1044:
1041:
1036:
1025:Biosynthesis
1009:
1001:
986:
969:
966:
939:
931:
919:
905:
898:
889:
869:
866:
853:
849:
848:
837:
831:
648:ChEMBL297812
461:
457:
453:
449:
445:
441:
437:
433:
411:Mostly fecal
394:Elimination
286:Legal status
280:Legal status
169:License data
29:
3653:from market
3623:Vorasidenib
3603:Trabectedin
3588:Tiazofurine
3583:Tebentafusp
3568:Tagraxofusp
3526:Plitidepsin
3496:Mitoguazone
3436:Epacadostat
3406:Demecolcine
3350:Aflibercept
3323:Sex steroid
3196:Fuzuloparib
3137:Carfilzomib
3109:Palbociclib
3099:Abemaciclib
3052:Verteporfin
3016:Efaproxiral
2932:Dacarbazine
2894:Altretamine
2876:Satraplatin
2871:Oxaliplatin
2851:Carboplatin
2828:Triaziquone
2799:Mannosulfan
2777:Ranimustine
2757:Fotemustine
2598:Pirarubicin
2583:Doxorubicin
2577:+cytarabine
2563:Aclarubicin
2524:Podophyllum
2449:Camptotheca
2380:Azacitidine
2366:Gemcitabine
2321:Floxuridine
2254:Fludarabine
2249:Clofarabine
2235:Halogenated
2226:Pentostatin
2201:Raltitrexed
2169:Aminopterin
2112:Ixabepilone
2107:Epothilones
2075:Cabazitaxel
2052:Vinorelbine
2037:Vincristine
2032:Vinblastine
2017:microtubule
1885:(1): 1388.
1554:12 November
1339:(1): 1–27.
1314:Proceedings
1204:6 September
1089:diphosphine
972:dacarbazine
954:liposarcoma
915:E. J. Corey
876:orphan drug
850:Trabectedin
758: g·mol
698:100.223.368
628:CHEBI:84050
483:114899-77-3
416:Identifiers
249:Intravenous
205:Trabectedin
155:MedlinePlus
128:Other names
119:Trade names
34:Trabectedin
3706:Categories
3618:Verdinexor
3613:Venetoclax
3516:Oblimersen
3511:Navitoclax
3486:Lucanthone
3481:Lonidamine
3471:Lifileucel
3466:Ivosidenib
3461:Imetelstat
3431:Enasidenib
3421:Elesclomol
3386:Bexarotene
3381:Belzutifan
3316:Bexarotene
3304:Atrasentan
3279:Umbralisib
3274:Idelalisib
3264:Copanlisib
3246:Vorinostat
3241:Romidepsin
3231:Entinostat
3226:Belinostat
3184:Masoprocol
3172:Tiazofurin
3160:Anagrelide
3132:Bortezomib
3119:Seliciclib
3114:Ribociclib
3094:inhibitors
3084:Tipifarnib
3047:Temoporfin
3042:Talaporfin
2980:Plicamycin
2975:Mitomycins
2921:Pipobroman
2900:Hydrazines
2866:Nedaplatin
2818:Carboquone
2813:Aziridines
2804:Treosulfan
2752:Carmustine
2739:Uramustine
2708:Ifosfamide
2680:Alkylating
2641:Bisantrene
2630:Pixantrone
2603:Valrubicin
2593:Idarubicin
2588:Epirubicin
2534:Teniposide
2489:Lurtotecan
2484:Irinotecan
2385:Decitabine
2349:Cytarabine
2292:Pyrimidine
2281:Tioguanine
2271:Thiopurine
2260:Nelarabine
2244:Cladribine
2196:Pemetrexed
2179:Pemetrexed
2155:Folic acid
2095:Paclitaxel
2047:Vinflunine
1923:"Yondelis"
1194:"Yondelis"
1177:References
1142:ETH Zürich
1042:Candidatus
946:ifosfamide
906:Candidatus
896:sea squirt
763:3D model (
751:Molar mass
588:ID0YZQ2TCP
559:ChemSpider
519:IUPHAR/BPS
474:CAS Number
425:IUPAC name
388:-mediated)
377:Metabolism
3663:Phase III
3651:Withdrawn
3628:Vosaroxin
3608:Veliparib
3563:Sotorasib
3553:Selinexor
3547:Tretinoin
3537:Retinoids
3451:Glasdegib
3396:Celecoxib
3345:Adagrasib
3269:Duvelisib
3259:Alpelisib
3214:Rucaparib
3201:Niraparib
3142:Oprozomib
3104:Alvocidib
2970:Bleomycin
2927:Triazenes
2911:Etoglucid
2856:Cisplatin
2772:Nimustine
2766:Semustine
2762:Lomustine
2724:Melphalan
2651:Menogaril
2646:Crisnatol
2636:Amsacrine
2608:Zorubicin
2568:Amrubicin
2529:Etoposide
2504:Topotecan
2499:Silatecan
2494:Rubitecan
2479:Gimatecan
2464:Cositecan
2454:Belotecan
2130:inhibitor
2100:Tesetaxel
2090:Ortataxel
2085:Larotaxel
2080:Docetaxel
2042:Vindesine
1832:Neoplasia
1712:PharmaMar
1093:catalyzed
1006:Structure
910:PharmaMar
407:Excretion
396:half-life
371:94 to 98%
242:Routes of
216:Pregnancy
147:Monograph
141:Drugs.com
3696:Medicine
3501:Mitotane
3441:Eribulin
3209:Olaparib
3147:Ixazomib
2823:Thiotepa
2795:Busulfan
2474:Exatecan
2311:Carmofur
2019:assembly
1982: /
1909:38360910
1862:21403840
1810:32586501
1751:20647340
1686:Archived
1527:10956543
1443:21875091
1361:25117225
1353:10608919
1255:DailyMed
1130:in vitro
1118:FUS-CHOP
1019:cysteine
1015:moieties
854:Yondelis
840:(verify)
539:DrugBank
384:(mostly
256:ATC code
218:category
200:DailyMed
123:Yondelis
18:Yondelis
3742:Phenols
2430:S phase
2331:Tegafur
2145:S phase
2070:Taxanes
2006:M phase
1853:3033593
1801:6169485
1759:6723817
1609:Reuters
1434:3220770
1087:-based
1085:rhodium
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715:Formula
548:DB05109
494:PubChem
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266: (
264:L01CX01
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161:a615059
110:-ti-din
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2015:Block
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1351:
1082:chiral
1080:, and
1076:, the
976:US FDA
789:SMILES
756:761.84
639:ChEMBL
608:D06199
508:108150
386:CYP3A4
327:℞-only
325:
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299:
198:
188:by INN
181:
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3167:IMPDI
3062:Other
1930:(EMA)
1755:S2CID
1692:7 May
1573:(PDF)
1544:(PDF)
1357:S2CID
1291:(EMA)
1224:(emc)
1146:UNIST
809:InChI
765:JSmol
619:ChEBI
568:97236
382:Liver
3253:PIKI
3221:HDAC
2670:CCNS
1938:2020
1905:PMID
1858:PMID
1806:PMID
1786:ISBN
1747:PMID
1694:2011
1617:2020
1556:2019
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1997:SPs
1988:L01
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