1012:, which sets the stereochemistry at C20. The desired configuration around C16 and C14 can then be fixed during the ensuing steps. In this pathway, vinblastine is constructed by a series of cyclization and coupling reactions which create the required stereochemistry. The overall yield may be as great as 22%, which makes this synthetic approach more attractive than extraction from natural sources, whose overall yield is about 10%. Stereochemistry is controlled through a mixture of chiral agents (Sharpless catalysts), and reaction conditions (temperature, and selected enantiopure starting materials). Due to difficulty of stereochemical restraints in total synthetic processes, other
592:
569:
47:
950:
1008:. Extraction is costly and yields of vinblastine and its precursors are low, although procedures for rapid isolation with improved yields avoiding auto-oxidation have been developed. Enantioselective synthesis has been of considerable interest in recent years, as the natural mixture of isomers is not an economical source for the required C16'S, C14'R stereochemistry of biologically active vinblastine. Initially, the approach depends upon an enantioselective
38:
3854:
661:
703:
InChI=1S/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37+,38-,39-,42+,43-,44-,45+,46+/m1/s1
966:
their organizing centers. Dose-response studies further indicate that enhanced microtubule detachment from spindle poles correlate best with cytotoxicity. But research into the mechanism is still ongoing as recent studies also show vinblastine inducing apoptosis that is phase-independent in certain leukemias.
1048:
plant. Vinblastine's utility as a chemotherapeutic agent was first suggested by its effect on the body when an extract of the plant was injected in rabbits to study the plant's supposed anti-diabetic effect. (A tea made from the plant was a folk-remedy for diabetes.) The rabbits died from a bacterial
965:
have been reported to act by two mechanisms. At very low concentrations they suppress microtubule dynamics and at higher concentrations they reduce microtubule polymer mass. Recent findings indicate that they also produce microtubule fragments by stimulating microtubule minus-end detachment from
1628:
Gobbi PG, Broglia C, Merli F, Dell'Olio M, Stelitano C, Iannitto E, et al. (December 2003). "Vinblastine, bleomycin, and methotrexate chemotherapy plus irradiation for patients with early-stage, favorable
Hodgkin lymphoma: the experience of the Gruppo Italiano Studio Linfomi".
865:
Adverse effects of vinblastine include hair loss, loss of white blood cells and blood platelets, gastrointestinal problems, high blood pressure, excessive sweating, depression, muscle cramps, vertigo and headaches. As a
940:
in VBM chemotherapy for Stage IA or IIA Hodgkin lymphomas. The inclusion of vinblastine allows for lower doses of bleomycin and reduced overall toxicity with larger resting periods between chemotherapy cycles.
1488:"Total synthesis of vinblastine, related natural products, and key analogues and development of inspired methodology suitable for the systematic study of their structure-function properties"
224:
1778:"Vinblastine induces acute, cell cycle phase-independent apoptosis in some leukemias and lymphomas and can induce acute apoptosis in others when Mcl-1 is suppressed"
3720:
3894:
179:
719:
2132:
2014:"A simplified procedure for indole alkaloid extraction from Catharanthus roseus combined with a semi-synthetic production process for vinblastine"
1359:
van Der
Heijden R, Jacobs DI, Snoeijer W, Hallard D, Verpoorte R (March 2004). "The Catharanthus alkaloids: pharmacognosy and biotechnology".
1193:
The selection and use of essential medicines 2023: web annex A: World Health
Organization model list of essential medicines: 23rd list (2023)
77:
1565:
3780:
2832:
1417:
675:
2661:
2641:
2626:
1174:
1143:
1101:
1611:
1308:
929:
injury (forms deep ulcers). Vinblastine paracrystals may be composed of tightly packed unpolymerized tubulin or microtubules.
3048:
3808:
2125:
826:
354:
dimethyl (2β,3β,4β,5α,12β,19α)-15-indol- 9-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3,4-dicarboxylate
1551:
1977:
Yokoshima S, Tokuyama H, Fukuyama T (2009). "Total
Synthesis of (+)-Vinblastine: Control of the Stereochemistry at C18′".
3415:
870:, vinblastine can cause extensive tissue damage and blistering if it escapes from the vein from improper administration.
1946:
Kuehne ME, Matson PA, Bornmann WG (1991). "Enantioselective
Syntheses of Vinblastine, Leurosidine, Vincovaline, and 20'-
2567:
2523:
2401:
726:
128:
2110:
2326:
1559:
1411:
1218:"Treatment of stage I and II Hodgkin's lymphoma with ABVD chemotherapy: results after 7 years of a prospective study"
1168:
1137:
695:
3825:
2118:
1860:
Tsuji A (October 1998). "P-glycoprotein-mediated efflux transport of anticancer drugs at the blood-brain barrier".
932:
Vinblastine is reported to be an effective component of certain chemotherapy regimens, particularly when used with
3879:
2842:
1727:"Inhibition of cell migration and cell division correlates with distinct effects of microtubule inhibiting drugs"
346:
209:
109:
3461:
2463:
2353:
3383:
3366:
3241:
3005:
2383:
1041:
3115:
2711:
587:
448:
1216:
Rueda DomĂnguez A, Márquez A, Gumá J, Llanos M, Herrero J, de Las Nieves MA, et al. (December 2004).
3884:
3317:
2063:
Noble RL, Beer CT, Cutts JH (December 1958). "Role of chance observations in chemotherapy: Vinca rosea".
975:
821:
that has since been developed into a conventional medicine, vinblastine was originally obtained from the
548:
2707:
2677:
1581:"Two ultrastructurally distinct tubulin paracrystals induced in sea-urchin eggs by vinblastine sulphate"
3844:
2497:
760:
683:
89CN(CCc1c(c2ccccc12)(C(=O)OC)(c3cc4c(cc3OC)N(C)5()(O)(C(=O)OC)(OC(C)=O)7(CC)C=CCN6CC4567)C8)C(O)(CC)C9
2602:
517:
3683:
3563:
3553:
1188:
3874:
3735:
3668:
3638:
3256:
2506:
1033:
564:
537:
3889:
3813:
3538:
3253:
2739:
2587:
2514:
914:
850:
748:
165:
59:
1334:
3618:
3608:
3341:
3183:
918:
1539:
1259:"Current Treatment Concepts for Extra-Abdominal Desmoid-Type Fibromatosis: A Narrative Review"
1158:
1127:
497:
2890:
2537:
1395:
1045:
1009:
822:
756:
437:
3288:
3165:
2686:
2072:
1097:
838:
457:
309:
87:
8:
3573:
3473:
3452:
3173:
2995:
2827:
2558:
2454:
1037:
996:
803:
799:
372:
363:
172:
2076:
1285:
1258:
591:
568:
2631:
2140:
2096:
2084:
2040:
2013:
1923:
1896:
1802:
1777:
1753:
1726:
1707:
1664:
1512:
1487:
1459:
1432:
139:
1838:
3755:
3329:
2163:
2088:
2045:
1994:
1928:
1877:
1873:
1842:
1825:
Schinkel AH (April 1999). "P-Glycoprotein, a gatekeeper in the blood-brain barrier".
1807:
1758:
1699:
1656:
1603:
1580:
1555:
1517:
1464:
1407:
1376:
1290:
1239:
1164:
1133:
811:
776:
261:
248:
236:
101:
2100:
1711:
1668:
1548:
The
Epothilones: An Outstanding Family of Anti-Tumor Agents: From Soil to the Clinic
1053:, so it was hypothesized that vinblastine might be effective against cancers of the
786:
Most people experience some side effects. Commonly it causes a change in sensation,
3760:
3517:
3232:
2866:
2851:
2572:
2080:
2035:
2025:
1986:
1959:
1918:
1908:
1869:
1834:
1797:
1789:
1748:
1738:
1691:
1682:
Jordan MA, Wilson L (April 2004). "Microtubules as a target for anticancer drugs".
1646:
1638:
1595:
1507:
1499:
1454:
1444:
1368:
1280:
1270:
1229:
1196:
1054:
846:
604:
397:
274:
192:
1897:"Biosynthesis and regulation of terpenoid indole alkaloids in Catharanthus roseus"
1793:
3858:
3199:
3161:
2952:
2374:
2289:
1129:
The evolution of drug discovery : from traditional medicines to modern drugs
902:
292:
282:
3819:
3353:
2944:
2438:
2302:
2189:
2159:
2146:
983:
879:
764:
2012:
Verma A, Laakso I, Seppänen-Laakso T, Huhtikangas A, Riekkola ML (July 2007).
1449:
3868:
3693:
3653:
3023:
2896:
2777:
2720:
2478:
2427:
1913:
1543:
1483:
1372:
1017:
1013:
1001:
1000:), its only known biological producer, along with several of its precursors,
926:
922:
854:
818:
580:
46:
1743:
1275:
1234:
1217:
29:
3740:
3704:
3588:
3578:
3532:
3528:
3490:
3398:
3188:
3127:
3123:
3104:
3099:
3078:
3067:
2881:
2875:
2861:
2856:
2787:
2782:
2735:
2621:
2488:
2468:
2397:
2346:
2336:
2150:
2142:
2092:
2049:
1998:
1932:
1846:
1811:
1762:
1703:
1660:
1521:
1468:
1380:
1294:
1243:
949:
937:
894:
787:
768:
528:
187:
1990:
1881:
3785:
3765:
3750:
3745:
3730:
3688:
3658:
3598:
3568:
3512:
3485:
3358:
3299:
3271:
3261:
3214:
3178:
3094:
3056:
3038:
3033:
3013:
2990:
2961:
2939:
2919:
2909:
2760:
2745:
2725:
2611:
2542:
2528:
2483:
2416:
2411:
2388:
2363:
2331:
2274:
2237:
2214:
2199:
2179:
1776:
Salerni BL, Bates DJ, Albershardt TC, Lowrey CH, Eastman A (April 2010).
1607:
906:
886:
857:
according to the established protocols of the
Histiocytosis Association.
780:
95:
20:
1963:
1599:
1540:"Preclinical Pharmacology and Structure-Activity Studies of Epothilones"
1201:
417:
3775:
3678:
3673:
3648:
3643:
3633:
3628:
3623:
3593:
3583:
3548:
3543:
3523:
3478:
3466:
3441:
3436:
3426:
3408:
3403:
3393:
3388:
3346:
3334:
3322:
3294:
3281:
3276:
3246:
3209:
3204:
3142:
3137:
3083:
3028:
2980:
2966:
2914:
2901:
2870:
2803:
2792:
2765:
2755:
2750:
2696:
2651:
2646:
2547:
2511:
2443:
2433:
2422:
2406:
2358:
2341:
2317:
2269:
2257:
2209:
1642:
1050:
962:
953:
The complex of tubulin and vinblastine. Vinblastine is shown in yellow.
909:, each of which are necessary for the separation of chromosomes during
898:
751:, typically used with other medications, to treat a number of types of
637:
428:
1651:
1503:
901:
arrest by disrupting microtubule assembly and proper formation of the
3790:
3770:
3725:
3715:
3709:
3613:
3558:
3507:
3431:
3421:
3376:
3363:
3304:
3266:
3194:
3132:
3073:
3062:
3018:
2975:
2934:
2928:
2924:
2886:
2813:
2808:
2798:
2770:
2730:
2691:
2666:
2656:
2616:
2262:
2252:
2247:
2242:
2204:
2030:
2011:
1433:"Modifications on the basic skeletons of vinblastine and vincristine"
1403:
1021:
1005:
933:
807:
795:
791:
383:
327:
322:
81:
1695:
1358:
3699:
3663:
3603:
3371:
3309:
3089:
2985:
2957:
2636:
2473:
1058:
958:
910:
867:
772:
477:
408:
123:
37:
660:
2592:
2493:
2307:
2168:
890:
1215:
1156:
2232:
752:
508:
331:
301:
1627:
1400:
Botanical
Miracles: Chemistry of Plants That Changed the World
1775:
979:
651:
488:
297:
994:
Vinblastine may be isolated from the
Madagascar Periwinkle (
553:
1430:
842:
468:
1257:
Lee YS, Joo MW, Shin SH, Hong S, Chung YG (January 2024).
1976:
1187:
1132:(1. Aufl. ed.). Weinheim: Wiley-VCH. p. 157.
827:
1431:
Keglevich P, Hazai L, Kalaus G, Szántay C (May 2012).
802:. It should not be given to people who have a current
3842:
1100:. The American Society of Health-System Pharmacists.
1945:
1309:"Vinblastine sulfate- vinblastine sulfate injection"
1157:Liljefors T, Krogsgaard-Larsen P, Madsen U (2002).
849:, and along with methotrexate in the treatment of
817:Vinblastine was isolated in 1958. An example of a
1724:
3866:
897:. Vinblastine treatment causes M phase specific
810:will likely harm the baby. Vinblastine works by
396:
1424:
957:Microtubule-disruptive drugs like vinblastine,
371:
2062:
1256:
3895:World Health Organization essential medicines
2126:
1121:
1119:
2056:
1894:
1818:
1725:Yang H, Ganguly A, Cabral F (October 2010).
1681:
1393:
536:
127:
1895:Zhu J, Wang M, Wen W, Yu R (January 2015).
1853:
266:In general: â„ž (Prescription only)
2133:
2119:
2065:Annals of the New York Academy of Sciences
1533:
1531:
1481:
1163:(Third ed.). CRC Press. p. 550.
1116:
1092:
1090:
1088:
1086:
1084:
1082:
1080:
1078:
1076:
1074:
989:
853:(desmoid tumor). It is also used to treat
837:Vinblastine is a component of a number of
590:
567:
436:
45:
36:
2039:
2029:
1922:
1912:
1801:
1752:
1742:
1650:
1511:
1458:
1448:
1284:
1274:
1233:
1200:
456:
1888:
1824:
1578:
948:
1568:from the original on 11 September 2017.
1537:
1528:
1071:
563:
416:
100:
3867:
1181:
1177:from the original on 20 December 2016.
1125:
944:
581:
242:
2114:
1859:
1617:from the original on 13 January 2014.
1552:Springer Science & Business Media
1195:. Geneva: World Health Organization.
1160:Textbook of Drug Design and Discovery
1051:decreased number of white blood cells
893:, thereby inhibiting the assembly of
516:
496:
255:
118:
86:
191:
2402:ribonucleotide reductase inhibitors
1731:The Journal of Biological Chemistry
1420:from the original on 1 August 2017.
1146:from the original on 1 August 2017.
1104:from the original on 2 January 2015
969:
476:
387:
13:
2568:Ribonucleotide reductase inhibitor
2524:Ribonucleotide reductase inhibitor
2085:10.1111/j.1749-6632.1958.tb54906.x
1061:. It was approved by FDA in 1965.
1032:Vinblastine was first isolated by
790:, weakness, loss of appetite, and
14:
3906:
2327:Dihydrofolate reductase inhibitor
218:
150:
3852:
1874:10.1097/00007691-199810000-00024
925:(blister-forming) activity, and
621:
615:
2005:
1970:
1939:
1769:
1718:
1675:
1621:
1572:
1475:
1387:
913:of mitosis. Toxicities include
873:
860:
832:
708:Key:JXLYSJRDGCGARV-XQKSVPLYSA-N
2464:Thymidylate synthase inhibitor
2354:Thymidylate synthase inhibitor
1352:
1327:
1301:
1250:
1209:
1150:
794:. Severe side effects include
627:
609:
231:
1:
2384:Adenosine deaminase inhibitor
2225:Block microtubule disassembly
1839:10.1016/s0169-409x(98)00085-4
1794:10.1158/1535-7163.MCT-10-0028
1782:Molecular Cancer Therapeutics
1492:Accounts of Chemical Research
1064:
1042:University of Western Ontario
743:), sold under the brand name
1952:Journal of Organic Chemistry
1396:"Africa's gift to the world"
1394:Cooper R, Deakin JJ (2016).
1024:, continue to be developed.
982:uptake caused by binding to
974:Vinblastine appears to be a
7:
1579:Starling D (January 1976).
1361:Current Medicinal Chemistry
976:peripherally selective drug
885:and a chemical analogue of
10:
3911:
1205:. WHO/MHP/HPS/EML/2023.02.
1027:
917:(which is dose-limiting),
761:non-small-cell lung cancer
599:Chemical and physical data
18:
3803:
3684:Omacetaxine mepesuccinate
3564:Ciltacabtagene autoleucel
3554:Brexucabtagene autoleucel
3500:
3451:
3231:
3224:
3160:
3114:
3047:
3004:
2841:
2826:
2706:
2676:
2601:
2586:
2557:
2453:
2373:
2316:
2299:
2288:
2224:
2177:
2158:
1450:10.3390/molecules17055893
1189:World Health Organization
1016:methods from precursors,
716:
691:
671:
649:
636:
603:
598:
579:
547:
527:
507:
487:
467:
447:
427:
407:
382:
362:
342:
337:
321:
308:
291:
281:
273:
208:
203:
178:
164:
138:
108:
94:
76:
68:
58:
53:
44:
35:
3736:Talimogene laherparepvec
3669:Nadofaragene firadenovec
3639:Lisocabtagene maraleucel
2588:Topoisomerase inhibitors
2507:DNA polymerase inhibitor
1914:10.4103/0973-7847.156323
1373:10.2174/0929867043455846
19:Not to be confused with
3539:Axicabtagene ciloleucel
2143:chemotherapeutic agents
1744:10.1074/jbc.M110.160820
1588:Journal of Cell Science
1276:10.3390/cancers16020273
990:Isolation and synthesis
915:bone marrow suppression
851:aggressive fibromatosis
749:chemotherapy medication
16:Chemotherapy medication
3880:Microtubule inhibitors
3721:Sitimagene ceradenovec
3619:Idecabtagene vicleucel
3184:Methyl aminolevulinate
1684:Nature Reviews. Cancer
954:
812:blocking cell division
3195:Porphyrin derivatives
2891:Melphalan flufenamide
2538:Hypomethylating agent
2147:antineoplastic agents
1991:10.1002/tcr.200900025
1901:Pharmacognosy Reviews
1235:10.1093/annonc/mdh465
1098:"Vinblastine Sulfate"
1046:Madagascar periwinkle
1010:Sharpless epoxidation
952:
839:chemotherapy regimens
823:Madagascar periwinkle
819:natural herbal remedy
796:low blood cell counts
781:injection into a vein
317:24.8 hours (terminal)
64:Velban, Velbe, others
3524:Asparagine depleters
3453:Receptor antagonists
3367:+abiraterone acetate
1554:. pp. 157–220.
1049:infection, due to a
3574:Denileukin diftitox
3474:Retinoid X receptor
3174:Aminolevulinic acid
2996:Triethylenemelamine
2828:Crosslinking of DNA
2559:Deoxyribonucleotide
2498:+gimeracil/oteracil
2077:1958NYASA..76..882N
1979:The Chemical Record
1964:10.1021/jo00002a008
1737:(42): 32242–32250.
1600:10.1242/jcs.20.1.79
1538:Altmann KH (2009).
1038:Charles Thomas Beer
997:Catharanthus roseus
945:Mechanism of action
804:bacterial infection
800:shortness of breath
747:among others, is a
251:(Prescription only)
227:(Prescription only)
32:
3885:Mitotic inhibitors
3830:Never to phase III
2632:Etirinotecan pegol
1827:Adv Drug Deliv Rev
1643:10.1002/cncr.11807
1406:. pp. 46–51.
1315:. 31 December 2019
1222:Annals of Oncology
955:
757:Hodgkin's lymphoma
72:vincaleukoblastine
28:
3840:
3839:
3799:
3798:
3756:Tigilanol tiglate
3233:Enzyme inhibitors
3156:
3155:
3152:
3151:
2852:Nitrogen mustards
2822:
2821:
2582:
2581:
2284:
2283:
1637:(11): 2393–2401.
1504:10.1021/ar500400w
1228:(12): 1798–1804.
1126:Ravina E (2011).
1055:white blood cells
921:toxicity, potent
878:Vinblastine is a
779:. It is given by
777:testicular cancer
734:
733:
662:Interactive image
549:CompTox Dashboard
259:
246:
234:
222:
154:
121:
3902:
3857:
3856:
3855:
3848:
3761:Tisagenlecleucel
3518:Arsenic trioxide
3229:
3228:
3162:Photosensitizers
2953:Alkyl sulfonates
2867:Cyclophosphamide
2839:
2838:
2778:Anthracenediones
2599:
2598:
2573:Hydroxycarbamide
2314:
2313:
2297:
2296:
2175:
2174:
2135:
2128:
2121:
2112:
2111:
2105:
2104:
2060:
2054:
2053:
2043:
2033:
2031:10.3390/12071307
2024:(7): 1307–1315.
2009:
2003:
2002:
1974:
1968:
1967:
1943:
1937:
1936:
1926:
1916:
1892:
1886:
1885:
1857:
1851:
1850:
1833:(2–3): 179–194.
1822:
1816:
1815:
1805:
1773:
1767:
1766:
1756:
1746:
1722:
1716:
1715:
1679:
1673:
1672:
1654:
1625:
1619:
1618:
1616:
1585:
1576:
1570:
1569:
1535:
1526:
1525:
1515:
1479:
1473:
1472:
1462:
1452:
1443:(5): 5893–5914.
1428:
1422:
1421:
1391:
1385:
1384:
1356:
1350:
1349:
1347:
1345:
1331:
1325:
1324:
1322:
1320:
1305:
1299:
1298:
1288:
1278:
1254:
1248:
1247:
1237:
1213:
1207:
1206:
1204:
1185:
1179:
1178:
1154:
1148:
1147:
1123:
1114:
1113:
1111:
1109:
1094:
970:Pharmacokinetics
919:gastrointestinal
847:Hodgkin lymphoma
825:. It is on the
755:. This includes
730:
729:
722:
664:
644:
629:
623:
617:
611:
594:
583:
572:
571:
557:
555:
540:
520:
500:
480:
460:
440:
420:
400:
390:
389:
375:
313:
257:
254:
244:
241:
233:
230:
220:
217:
195:
152:
149:
131:
120:
117:
104:
90:
49:
40:
33:
31:
27:
3910:
3909:
3905:
3904:
3903:
3901:
3900:
3899:
3875:Vinca alkaloids
3865:
3864:
3863:
3853:
3851:
3843:
3841:
3836:
3835:
3820:Clinical trials
3795:
3501:Other/ungrouped
3496:
3447:
3220:
3200:Porfimer sodium
3148:
3110:
3043:
3000:
2830:
2818:
2702:
2672:
2590:
2578:
2553:
2449:
2369:
2305:
2303:antimetabolites
2301:
2300:DNA precursors/
2292:
2290:DNA replication
2280:
2220:
2190:Vinca alkaloids
2166:
2154:
2139:
2109:
2108:
2061:
2057:
2010:
2006:
1975:
1971:
1950:-Vincovaline".
1944:
1940:
1893:
1889:
1862:Ther Drug Monit
1858:
1854:
1823:
1819:
1774:
1770:
1723:
1719:
1696:10.1038/nrc1317
1680:
1676:
1626:
1622:
1614:
1583:
1577:
1573:
1562:
1536:
1529:
1480:
1476:
1429:
1425:
1414:
1392:
1388:
1357:
1353:
1343:
1341:
1333:
1332:
1328:
1318:
1316:
1307:
1306:
1302:
1255:
1251:
1214:
1210:
1186:
1182:
1171:
1155:
1151:
1140:
1124:
1117:
1107:
1105:
1096:
1095:
1072:
1067:
1030:
992:
978:due to limited
972:
947:
903:mitotic spindle
876:
863:
835:
725:
723:
720:(what is this?)
717:
712:
709:
704:
699:
698:
687:
684:
679:
678:
667:
642:
632:
626:
620:
614:
575:
551:
543:
523:
503:
483:
463:
443:
423:
403:
386:
378:
358:
355:
350:
349:
311:
283:Bioavailability
275:Pharmacokinetic
269:
199:
167:
160:
141:
134:
24:
17:
12:
11:
5:
3908:
3898:
3897:
3892:
3890:Acetate esters
3887:
3882:
3877:
3862:
3861:
3838:
3837:
3834:
3833:
3832:
3831:
3828:
3817:
3811:
3805:
3804:
3801:
3800:
3797:
3796:
3794:
3793:
3788:
3783:
3778:
3773:
3768:
3763:
3758:
3753:
3748:
3743:
3738:
3733:
3728:
3723:
3718:
3713:
3707:
3696:
3691:
3686:
3681:
3676:
3671:
3666:
3661:
3656:
3651:
3646:
3641:
3636:
3631:
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3536:
3520:
3515:
3510:
3504:
3502:
3498:
3497:
3495:
3494:
3482:
3470:
3457:
3455:
3449:
3448:
3446:
3445:
3439:
3434:
3429:
3424:
3412:
3406:
3401:
3396:
3391:
3380:
3374:
3369:
3361:
3354:PARP inhibitor
3350:
3338:
3326:
3314:
3313:
3312:
3307:
3302:
3297:
3285:
3279:
3274:
3269:
3264:
3250:
3237:
3235:
3226:
3222:
3221:
3219:
3218:
3212:
3207:
3202:
3191:
3186:
3181:
3176:
3170:
3168:
3158:
3157:
3154:
3153:
3150:
3149:
3147:
3146:
3140:
3135:
3130:
3120:
3118:
3112:
3111:
3109:
3108:
3102:
3097:
3086:
3081:
3076:
3071:
3059:
3053:
3051:
3045:
3044:
3042:
3041:
3036:
3031:
3026:
3021:
3016:
3010:
3008:
3006:Platinum-based
3002:
3001:
2999:
2998:
2993:
2988:
2983:
2971:
2970:
2964:
2948:
2947:
2942:
2937:
2932:
2922:
2917:
2905:
2904:
2899:
2894:
2884:
2879:
2873:
2864:
2859:
2847:
2845:
2836:
2824:
2823:
2820:
2819:
2817:
2816:
2811:
2806:
2801:
2796:
2790:
2785:
2774:
2768:
2763:
2758:
2753:
2748:
2743:
2733:
2728:
2721:Anthracyclines
2716:
2714:
2704:
2703:
2701:
2700:
2694:
2682:
2680:
2674:
2673:
2671:
2670:
2664:
2659:
2654:
2649:
2644:
2639:
2634:
2629:
2624:
2619:
2607:
2605:
2596:
2584:
2583:
2580:
2579:
2577:
2576:
2563:
2561:
2555:
2554:
2552:
2551:
2545:
2533:
2532:
2519:
2518:
2502:
2501:
2491:
2486:
2481:
2476:
2471:
2459:
2457:
2451:
2450:
2448:
2447:
2441:
2439:Mercaptopurine
2430:
2425:
2420:
2414:
2409:
2393:
2392:
2379:
2377:
2371:
2370:
2368:
2367:
2361:
2350:
2344:
2339:
2334:
2322:
2320:
2311:
2294:
2286:
2285:
2282:
2281:
2279:
2278:
2266:
2260:
2255:
2250:
2245:
2240:
2228:
2226:
2222:
2221:
2219:
2218:
2212:
2207:
2202:
2197:
2185:
2183:
2172:
2156:
2155:
2141:Intracellular
2138:
2137:
2130:
2123:
2115:
2107:
2106:
2071:(3): 882–894.
2055:
2004:
1985:(2): 101–118.
1969:
1958:(2): 513–528.
1938:
1887:
1852:
1817:
1788:(4): 791–802.
1768:
1717:
1690:(4): 253–265.
1674:
1620:
1571:
1560:
1527:
1498:(3): 653–662.
1486:(March 2015).
1474:
1423:
1412:
1386:
1367:(5): 607–628.
1351:
1326:
1300:
1249:
1208:
1180:
1169:
1149:
1138:
1115:
1069:
1068:
1066:
1063:
1029:
1026:
1014:semi-synthetic
991:
988:
984:P-glycoprotein
971:
968:
946:
943:
875:
872:
862:
859:
834:
831:
765:bladder cancer
732:
731:
714:
713:
711:
710:
707:
705:
702:
694:
693:
692:
689:
688:
686:
685:
682:
674:
673:
672:
669:
668:
666:
665:
657:
655:
647:
646:
640:
634:
633:
630:
624:
618:
612:
607:
601:
600:
596:
595:
585:
577:
576:
574:
573:
560:
558:
545:
544:
542:
541:
533:
531:
525:
524:
522:
521:
513:
511:
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:
380:
379:
377:
376:
368:
366:
360:
359:
357:
356:
353:
345:
344:
343:
340:
339:
335:
334:
325:
319:
318:
315:
306:
305:
295:
289:
288:
285:
279:
278:
271:
270:
268:
267:
264:
252:
239:
228:
214:
212:
206:
205:
201:
200:
198:
197:
184:
182:
176:
175:
170:
168:administration
162:
161:
159:
158:
156:
146:
144:
136:
135:
133:
132:
114:
112:
106:
105:
98:
92:
91:
84:
74:
73:
70:
66:
65:
62:
56:
55:
51:
50:
42:
41:
15:
9:
6:
4:
3:
2:
3907:
3896:
3893:
3891:
3888:
3886:
3883:
3881:
3878:
3876:
3873:
3872:
3870:
3860:
3850:
3849:
3846:
3829:
3827:
3824:
3823:
3821:
3818:
3815:
3812:
3810:
3807:
3806:
3802:
3792:
3789:
3787:
3784:
3782:
3779:
3777:
3774:
3772:
3769:
3767:
3764:
3762:
3759:
3757:
3754:
3752:
3749:
3747:
3744:
3742:
3739:
3737:
3734:
3732:
3729:
3727:
3724:
3722:
3719:
3717:
3714:
3711:
3708:
3706:
3702:
3701:
3697:
3695:
3694:Tabelecleucel
3692:
3690:
3687:
3685:
3682:
3680:
3677:
3675:
3672:
3670:
3667:
3665:
3662:
3660:
3657:
3655:
3654:Lurbinectedin
3652:
3650:
3647:
3645:
3642:
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3622:
3620:
3617:
3615:
3612:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3534:
3530:
3526:
3525:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3505:
3503:
3499:
3492:
3488:
3487:
3483:
3480:
3476:
3475:
3471:
3468:
3464:
3463:
3459:
3458:
3456:
3454:
3450:
3443:
3440:
3438:
3435:
3433:
3430:
3428:
3425:
3423:
3419:
3417:
3413:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3386:
3385:
3381:
3378:
3375:
3373:
3370:
3368:
3365:
3362:
3360:
3356:
3355:
3351:
3348:
3344:
3343:
3339:
3336:
3332:
3331:
3327:
3324:
3320:
3319:
3315:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3292:
3291:
3290:
3286:
3283:
3280:
3278:
3275:
3273:
3270:
3268:
3265:
3263:
3259:
3258:
3255:
3251:
3248:
3244:
3243:
3239:
3238:
3236:
3234:
3230:
3227:
3223:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3197:
3196:
3192:
3190:
3187:
3185:
3182:
3180:
3177:
3175:
3172:
3171:
3169:
3167:
3163:
3159:
3144:
3141:
3139:
3136:
3134:
3131:
3129:
3125:
3122:
3121:
3119:
3117:
3116:Intercalation
3113:
3106:
3103:
3101:
3098:
3096:
3092:
3091:
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3069:
3065:
3064:
3060:
3058:
3055:
3054:
3052:
3050:
3046:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3024:Dicycloplatin
3022:
3020:
3017:
3015:
3012:
3011:
3009:
3007:
3003:
2997:
2994:
2992:
2989:
2987:
2984:
2982:
2979:
2977:
2973:
2972:
2968:
2965:
2963:
2959:
2956:
2954:
2950:
2949:
2946:
2943:
2941:
2938:
2936:
2933:
2930:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2907:
2906:
2903:
2900:
2898:
2897:Prednimustine
2895:
2892:
2888:
2885:
2883:
2880:
2877:
2874:
2872:
2868:
2865:
2863:
2860:
2858:
2855:
2853:
2849:
2848:
2846:
2844:
2840:
2837:
2834:
2829:
2825:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2794:
2791:
2789:
2786:
2784:
2780:
2779:
2775:
2772:
2769:
2767:
2764:
2762:
2759:
2757:
2754:
2752:
2749:
2747:
2744:
2741:
2737:
2734:
2732:
2729:
2727:
2723:
2722:
2718:
2717:
2715:
2713:
2712:Intercalation
2709:
2705:
2698:
2695:
2693:
2689:
2688:
2684:
2683:
2681:
2679:
2675:
2668:
2665:
2663:
2660:
2658:
2655:
2653:
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2614:
2613:
2609:
2608:
2606:
2604:
2600:
2597:
2594:
2589:
2585:
2574:
2570:
2569:
2565:
2564:
2562:
2560:
2556:
2549:
2546:
2544:
2540:
2539:
2535:
2534:
2530:
2526:
2525:
2521:
2520:
2516:
2515:+daunorubicin
2513:
2509:
2508:
2504:
2503:
2499:
2495:
2492:
2490:
2487:
2485:
2482:
2480:
2479:Doxifluridine
2477:
2475:
2472:
2470:
2466:
2465:
2461:
2460:
2458:
2456:
2452:
2445:
2442:
2440:
2436:
2435:
2431:
2429:
2428:Rabacfosadine
2426:
2424:
2421:
2418:
2415:
2413:
2410:
2408:
2404:
2403:
2399:
2395:
2394:
2390:
2386:
2385:
2381:
2380:
2378:
2376:
2372:
2365:
2362:
2360:
2356:
2355:
2351:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2329:
2328:
2324:
2323:
2321:
2319:
2315:
2312:
2309:
2304:
2298:
2295:
2291:
2287:
2276:
2272:
2271:
2267:
2264:
2261:
2259:
2256:
2254:
2251:
2249:
2246:
2244:
2241:
2239:
2235:
2234:
2230:
2229:
2227:
2223:
2216:
2213:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2192:
2191:
2187:
2186:
2184:
2181:
2176:
2173:
2170:
2165:
2161:
2157:
2152:
2148:
2144:
2136:
2131:
2129:
2124:
2122:
2117:
2116:
2113:
2102:
2098:
2094:
2090:
2086:
2082:
2078:
2074:
2070:
2066:
2059:
2051:
2047:
2042:
2037:
2032:
2027:
2023:
2019:
2015:
2008:
2000:
1996:
1992:
1988:
1984:
1980:
1973:
1965:
1961:
1957:
1953:
1949:
1942:
1934:
1930:
1925:
1920:
1915:
1910:
1907:(17): 24–28.
1906:
1902:
1898:
1891:
1883:
1879:
1875:
1871:
1868:(5): 588–90.
1867:
1863:
1856:
1848:
1844:
1840:
1836:
1832:
1828:
1821:
1813:
1809:
1804:
1799:
1795:
1791:
1787:
1783:
1779:
1772:
1764:
1760:
1755:
1750:
1745:
1740:
1736:
1732:
1728:
1721:
1713:
1709:
1705:
1701:
1697:
1693:
1689:
1685:
1678:
1670:
1666:
1662:
1658:
1653:
1648:
1644:
1640:
1636:
1632:
1624:
1613:
1609:
1605:
1601:
1597:
1593:
1589:
1582:
1575:
1567:
1563:
1561:9783211782071
1557:
1553:
1549:
1545:
1541:
1534:
1532:
1523:
1519:
1514:
1509:
1505:
1501:
1497:
1493:
1489:
1485:
1478:
1470:
1466:
1461:
1456:
1451:
1446:
1442:
1438:
1434:
1427:
1419:
1415:
1413:9781498704304
1409:
1405:
1401:
1397:
1390:
1382:
1378:
1374:
1370:
1366:
1362:
1355:
1340:
1336:
1335:"Vinblastine"
1330:
1314:
1310:
1304:
1296:
1292:
1287:
1282:
1277:
1272:
1268:
1264:
1260:
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1223:
1219:
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1198:
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1170:9780415282888
1166:
1162:
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1141:
1139:9783527326693
1135:
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1122:
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1062:
1060:
1056:
1052:
1047:
1043:
1039:
1035:
1025:
1023:
1019:
1018:catharanthine
1015:
1011:
1007:
1003:
1002:catharanthine
999:
998:
987:
985:
981:
977:
967:
964:
960:
951:
942:
939:
935:
930:
928:
927:extravasation
924:
920:
916:
912:
908:
904:
900:
896:
892:
888:
884:
882:
871:
869:
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855:histiocytosis
852:
848:
844:
840:
830:
828:
824:
820:
815:
813:
809:
806:. Use during
805:
801:
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793:
789:
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770:
766:
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728:
721:
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701:
700:
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690:
681:
680:
677:
670:
663:
659:
658:
656:
653:
648:
641:
639:
635:
608:
606:
602:
597:
593:
589:
586:
584:
582:ECHA InfoCard
578:
570:
566:
565:DTXSID8021430
562:
561:
559:
550:
546:
539:
535:
534:
532:
530:
526:
519:
515:
514:
512:
510:
506:
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459:
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194:
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177:
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148:
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137:
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125:
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107:
103:
99:
97:
93:
89:
85:
83:
79:
75:
71:
67:
63:
61:
57:
54:Clinical data
52:
48:
43:
39:
34:
26:
22:
3741:Tazemetostat
3705:Alitretinoin
3698:
3609:Estramustine
3589:Elsamitrucin
3579:Eflornithine
3533:Pegaspargase
3529:Asparaginase
3522:
3491:Testolactone
3484:
3472:
3460:
3414:
3399:Panobinostat
3382:
3352:
3340:
3328:
3316:
3287:
3252:
3240:
3193:
3189:Padeliporfin
3128:Dactinomycin
3124:Streptomyces
3105:Temozolomide
3100:Mitozolomide
3088:
3079:Mitobronitol
3068:Procarbazine
3061:
3049:Nonclassical
2974:
2951:
2945:Streptozocin
2910:Nitrosoureas
2908:
2882:Chlorambucil
2876:Trofosfamide
2862:Chlormethine
2857:Bendamustine
2850:
2788:Mitoxantrone
2783:Losoxantrone
2776:
2736:Daunorubicin
2719:
2685:
2622:Camptothecin
2610:
2566:
2536:
2522:
2505:
2489:Fluorouracil
2469:Capecitabine
2462:
2432:
2396:
2382:
2352:
2347:Pralatrexate
2337:Methotrexate
2325:
2268:
2231:
2194:
2188:
2068:
2064:
2058:
2021:
2017:
2007:
1982:
1978:
1972:
1955:
1951:
1947:
1941:
1904:
1900:
1890:
1865:
1861:
1855:
1830:
1826:
1820:
1785:
1781:
1771:
1734:
1730:
1720:
1687:
1683:
1677:
1634:
1630:
1623:
1594:(1): 79–89.
1591:
1587:
1574:
1547:
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1477:
1440:
1436:
1426:
1399:
1389:
1364:
1360:
1354:
1342:. Retrieved
1338:
1329:
1317:. Retrieved
1312:
1303:
1266:
1262:
1252:
1225:
1221:
1211:
1202:10665/371090
1192:
1183:
1159:
1152:
1128:
1106:. Retrieved
1034:Robert Noble
1031:
995:
993:
973:
956:
938:methotrexate
931:
895:microtubules
880:
877:
874:Pharmacology
864:
861:Side effects
841:, including
836:
833:Medical uses
816:
788:constipation
785:
769:brain cancer
744:
740:
736:
735:
724:
718:
529:NIAID ChemDB
310:Elimination
210:Legal status
204:Legal status
110:License data
25:
3816:from market
3786:Vorasidenib
3766:Trabectedin
3751:Tiazofurine
3746:Tebentafusp
3731:Tagraxofusp
3689:Plitidepsin
3659:Mitoguazone
3599:Epacadostat
3569:Demecolcine
3513:Aflibercept
3486:Sex steroid
3359:Fuzuloparib
3300:Carfilzomib
3272:Palbociclib
3262:Abemaciclib
3215:Verteporfin
3179:Efaproxiral
3095:Dacarbazine
3057:Altretamine
3039:Satraplatin
3034:Oxaliplatin
3014:Carboplatin
2991:Triaziquone
2962:Mannosulfan
2940:Ranimustine
2920:Fotemustine
2761:Pirarubicin
2746:Doxorubicin
2740:+cytarabine
2726:Aclarubicin
2687:Podophyllum
2612:Camptotheca
2543:Azacitidine
2529:Gemcitabine
2484:Floxuridine
2417:Fludarabine
2412:Clofarabine
2398:Halogenated
2389:Pentostatin
2364:Raltitrexed
2332:Aminopterin
2275:Ixabepilone
2270:Epothilones
2238:Cabazitaxel
2215:Vinorelbine
2200:Vincristine
2195:Vinblastine
2180:microtubule
1344:12 November
907:kinetochore
889:. It binds
887:vincristine
737:Vinblastine
645: g·mol
588:100.011.577
498:CHEBI:27375
338:Identifiers
173:intravenous
129:Vinblastine
96:MedlinePlus
69:Other names
60:Trade names
30:Vinblastine
21:vincristine
3869:Categories
3781:Verdinexor
3776:Venetoclax
3679:Oblimersen
3674:Navitoclax
3649:Lucanthone
3644:Lonidamine
3634:Lifileucel
3629:Ivosidenib
3624:Imetelstat
3594:Enasidenib
3584:Elesclomol
3549:Bexarotene
3544:Belzutifan
3479:Bexarotene
3467:Atrasentan
3442:Umbralisib
3437:Idelalisib
3427:Copanlisib
3409:Vorinostat
3404:Romidepsin
3394:Entinostat
3389:Belinostat
3347:Masoprocol
3335:Tiazofurin
3323:Anagrelide
3295:Bortezomib
3282:Seliciclib
3277:Ribociclib
3257:inhibitors
3247:Tipifarnib
3210:Temoporfin
3205:Talaporfin
3143:Plicamycin
3138:Mitomycins
3084:Pipobroman
3063:Hydrazines
3029:Nedaplatin
2981:Carboquone
2976:Aziridines
2967:Treosulfan
2915:Carmustine
2902:Uramustine
2871:Ifosfamide
2843:Alkylating
2804:Bisantrene
2793:Pixantrone
2766:Valrubicin
2756:Idarubicin
2751:Epirubicin
2697:Teniposide
2652:Lurtotecan
2647:Irinotecan
2548:Decitabine
2512:Cytarabine
2455:Pyrimidine
2444:Tioguanine
2434:Thiopurine
2423:Nelarabine
2407:Cladribine
2359:Pemetrexed
2342:Pemetrexed
2318:Folic acid
2258:Paclitaxel
2210:Vinflunine
1652:11380/4847
1482:Sears JE,
1269:(2): 273.
1065:References
963:nocodazole
899:cell cycle
650:3D model (
638:Molar mass
458:5V9KLZ54CY
429:ChemSpider
364:CAS Number
347:IUPAC name
304:-mediated)
293:Metabolism
3826:Phase III
3814:Withdrawn
3791:Vosaroxin
3771:Veliparib
3726:Sotorasib
3716:Selinexor
3710:Tretinoin
3700:Retinoids
3614:Glasdegib
3559:Celecoxib
3508:Adagrasib
3432:Duvelisib
3422:Alpelisib
3377:Rucaparib
3364:Niraparib
3305:Oprozomib
3267:Alvocidib
3133:Bleomycin
3090:Triazenes
3074:Etoglucid
3019:Cisplatin
2935:Nimustine
2929:Semustine
2925:Lomustine
2887:Melphalan
2814:Menogaril
2809:Crisnatol
2799:Amsacrine
2771:Zorubicin
2731:Amrubicin
2692:Etoposide
2667:Topotecan
2662:Silatecan
2657:Rubitecan
2642:Gimatecan
2627:Cositecan
2617:Belotecan
2293:inhibitor
2263:Tesetaxel
2253:Ortataxel
2248:Larotaxel
2243:Docetaxel
2205:Vindesine
2018:Molecules
1544:Mulzer JH
1437:Molecules
1404:CRC Press
1339:Chemocare
1108:2 January
1044:from the
1022:vindoline
1006:vindoline
934:bleomycin
808:pregnancy
792:headaches
518:ChEMBL159
328:Bile duct
323:Excretion
312:half-life
166:Routes of
140:Pregnancy
88:Monograph
82:Drugs.com
3859:Medicine
3664:Mitotane
3604:Eribulin
3372:Olaparib
3310:Ixazomib
2986:Thiotepa
2958:Busulfan
2637:Exatecan
2474:Carmofur
2182:assembly
2145: /
2101:34879726
2093:13627916
2050:17909486
1999:20394103
1933:26009689
1847:10837715
1812:20371726
1763:20696757
1712:10228718
1704:15057285
1669:21376280
1661:14635074
1612:Archived
1566:Archived
1522:25586069
1484:Boger DL
1469:22609781
1418:Archived
1381:15032608
1319:15 April
1313:DailyMed
1295:38254764
1286:10813957
1244:15550585
1191:(2023).
1175:Archived
1144:Archived
1102:Archived
1059:lymphoma
1057:such as
959:colcemid
923:vesicant
911:anaphase
905:and the
883:alkaloid
868:vesicant
773:melanoma
727:(verify)
409:DrugBank
373:865-21-4
180:ATC code
142:category
124:DailyMed
2593:S phase
2494:Tegafur
2308:S phase
2233:Taxanes
2169:M phase
2073:Bibcode
2041:6149338
1924:4441158
1882:9780140
1803:2852489
1754:2952225
1546:(ed.).
1513:4363169
1460:6268133
1263:Cancers
1040:at the
1028:History
891:tubulin
643:810.989
605:Formula
418:DB00570
384:PubChem
235::
196:)
190: (
188:L01CA01
155: D
126::
102:a682848
3845:Portal
3809:WHO-EM
3418:(Pi3K)
2375:Purine
2178:Block
2099:
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1997:
1931:
1921:
1880:
1845:
1810:
1800:
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1631:Cancer
1608:942954
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1293:
1283:
1242:
1167:
1136:
961:, and
775:, and
753:cancer
745:Velban
676:SMILES
538:002673
509:ChEMBL
478:D08675
438:211446
398:241903
332:kidney
302:CYP3A4
262:â„ž-only
260:
247:
237:â„ž-only
223:
122:
3330:IMPDI
3225:Other
2097:S2CID
1708:S2CID
1665:S2CID
1615:(PDF)
1584:(PDF)
1542:. In
980:brain
881:vinca
696:InChI
652:JSmol
489:ChEBI
298:Liver
3416:PIKI
3384:HDAC
2833:CCNS
2089:PMID
2046:PMID
1995:PMID
1929:PMID
1878:PMID
1843:PMID
1808:PMID
1759:PMID
1700:PMID
1657:PMID
1604:PMID
1556:ISBN
1518:PMID
1465:PMID
1408:ISBN
1377:PMID
1346:2021
1321:2020
1291:PMID
1240:PMID
1165:ISBN
1134:ISBN
1110:2015
1036:and
1020:and
1004:and
936:and
845:for
843:ABVD
798:and
469:KEGG
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330:and
277:data
78:AHFS
3462:ERA
3318:PhI
3289:PrI
3254:CDK
3166:PDT
2164:MIs
2160:SPs
2151:L01
2081:doi
2036:PMC
2026:doi
1987:doi
1960:doi
1948:epi
1919:PMC
1909:doi
1870:doi
1835:doi
1798:PMC
1790:doi
1749:PMC
1739:doi
1735:285
1692:doi
1647:hdl
1639:doi
1596:doi
1508:PMC
1500:doi
1455:PMC
1445:doi
1369:doi
1281:PMC
1271:doi
1230:doi
1197:hdl
741:VBL
554:EPA
388:CID
287:n/a
249:POM
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