724:
intracerebroventricular (ICV) infusion) has been used to develop an animal model of brain insulin resistance to mimic in rodents the pathophysiology of sporadic AD, which represents the most common form of AD in humans. STZ infusion in the brain induced accumulation of
Amyloid beta (AΞ²) protein, oxidative stress and cognitive impairment. Notably, there is now evidence that STZ infusion within the brain produced up-regulation of amyloid precursor protein (APP), tau hyperphosphorylation and neuroinflammation. Treatment with the cleavage-specific anti-tau 12A12 monoclonal antibody (mAb) can relieve APP upregulation, neuroinflammation and reduce cerebral oxidative stress, mitochondrial impairment, synaptic and histological alterations, as well as induce a nearly complete recovery of cognitive impairment in the STZ-induced SAD mouse model.
387:
29:
723:
More recently, a growing body of studies has provided evidence that derangement of insulin signaling underlying type-2 diabetes significantly increase the risk of cognitive impairment and
Alzheimer's disease (AD) progression. On this ground, the direct administration of STZ in the brain (i.e., by
610:. Since it carries a substantial risk of toxicity and rarely cures the cancer, its use is generally limited to patients whose cancer cannot be removed by surgery. In these patients, streptozotocin can reduce the tumor size and reduce symptoms (especially
460:
720:
filed for FDA approval of streptozotocin as a treatment for pancreatic islet cell cancer in
November 1976, and approval was granted in July 1982. The drug was subsequently marketed as Zanosar.
1119:
Murray-Lyon IM, Eddleston AL, Williams R, Brown M, Hogbin BM, Bennett A, et al. (October 1968). "Treatment of multiple-hormone-producing malignant islet-cell tumour with streptozotocin".
661:
which is likely more important for diabetes induction than the DNA damage itself. Streptozotocin is similar enough to glucose to be transported into the cell by the glucose transport protein
1360:
704:
In the mid-1960s, streptozotocin was found to be selectively toxic to the beta cells of the pancreatic islets, the cells that normally regulate blood glucose levels by producing the
79:
518:
1387:
1258:
Sharma M, Gupta YK (January 2001). "Intracerebroventricular injection of streptozotocin in rats produces both oxidative stress in the brain and cognitive impairment".
665:, but is not recognized by the other glucose transporters. This explains its relative toxicity to beta cells, since these cells have relatively high levels of GLUT2.
952:
Wang Z, Gleichmann H (January 1998). "GLUT2 in pancreatic islets: crucial target molecule in diabetes induced with multiple low doses of streptozotocin in mice".
708:
insulin. This suggested the drug's use as an animal model of diabetes, and as a medical treatment for cancers of the beta cells. In the 1960s and 1970s, the
2087:
474:
3092:
987:
Schnedl WJ, Ferber S, Johnson JH, Newgard CB (November 1994). "STZ transport and cytotoxicity. Specific enhancement in GLUT2-expressing cells".
3048:
1380:
1210:"Staging of cognitive deficits and neuropathological and ultrastructural changes in streptozotocin-induced rat model of Alzheimer's disease"
695:, which can therefore be considered the birthplace of streptozotocin. Upjohn filed for patent protection for the drug in August 1958 and
3102:
2670:
1049:
Mansford KR, Opie L (March 1968). "Comparison of metabolic abnormalities in diabetes mellitus induced by streptozotocin or by alloxan".
3097:
1822:
1778:
1656:
1581:
543:
494:
1085:
1373:
2303:
2097:
650:
180:
109:
2716:
1718:
1608:
2638:
2621:
2496:
2260:
1638:
2370:
1966:
658:
599:
286:
3065:
2572:
1365:
366:
502:
InChI=1S/C8H15N3O7/c1-11(10-17)8(16)9-4-6(14)5(13)3(2-12)18-7(4)15/h3-7,12-15H,2H2,1H3,(H,9,16)/t3-,4-,5-,6-,7+/m1/s1
625:
Due to its high toxicity to beta cells, in scientific research, streptozotocin has also been long used for inducing
1752:
547:
2928:
2818:
2808:
753:
709:
679:
2975:
2511:
1761:
583:
554:) is a naturally occurring alkylating antineoplastic agent that is particularly toxic to the insulin-producing
1022:
Vavra JJ, Deboer C, Dietz A, Hanka LJ, Sokolski WT (1959). "Streptozotocin, a new antibacterial antibiotic".
790:
Brentjens R, Saltz L (June 2001). "Islet cell tumors of the pancreas: the medical oncologist's perspective".
757:
and identified novel function of a non-heme iron enzyme, SznF, which forms the N-N bond in the N-nitrosourea
3053:
2960:
2793:
2508:
1994:
1842:
1769:
65:
2873:
2863:
2596:
2438:
1208:
Knezovic A, Osmanovic-Barilar J, Curlin M, Hof PR, Simic G, Riederer P, Salkovic-Petrisic M (April 2015).
925:
Szkudelski T (2001). "The mechanism of alloxan and streptozotocin action in B cells of the rat pancreas".
355:
3112:
3107:
2145:
1962:
1932:
1792:
567:
622:). A typical dose is 500 mg/m/day by intravenous injection, for 5 days, repeated every 4β6 weeks.
2543:
2420:
1941:
1857:
1306:
838:
607:
159:
2828:
2728:
2707:
2428:
2250:
2082:
1813:
1709:
692:
688:
630:
382:
201:
72:
633:. Streptozotocin has also been used for modeling Alzheimer's disease through memory loss in mice.
1886:
1240:
1190:
3020:
1916:
1896:
1881:
2995:
2584:
1418:
1332:
1275:
1232:
1182:
1136:
1105:
1097:
1066:
1031:
1004:
969:
934:
907:
866:
807:
587:
41:
335:
3000:
2772:
2487:
2121:
2106:
1827:
1322:
1314:
1267:
1224:
1209:
1172:
1128:
1058:
996:
961:
897:
856:
846:
799:
403:
125:
295:
275:
210:
2454:
2416:
2207:
1629:
1544:
740:
143:
133:
1310:
842:
386:
3117:
3059:
2608:
1693:
1557:
1444:
1414:
1401:
1327:
1294:
579:
28:
1271:
1132:
1062:
861:
826:
803:
3086:
2903:
2278:
2151:
2032:
1975:
1733:
1682:
758:
575:
57:
1244:
2980:
2944:
2843:
2833:
2787:
2783:
2745:
2653:
2443:
2382:
2378:
2359:
2354:
2333:
2322:
2136:
2130:
2116:
2111:
2042:
2037:
1990:
1876:
1743:
1723:
1652:
1601:
1591:
1405:
1397:
1194:
1161:"Risk of developing dementia in people with diabetes and mild cognitive impairment"
748:
736:
727:
Streptozotocin is now long off patent and many generic formulations are available.
713:
611:
571:
92:
87:
1159:
Velayudhan L, Poppe M, Archer N, Proitsi P, Brown RG, Lovestone S (January 2010).
235:
3025:
3005:
2990:
2985:
2970:
2933:
2908:
2853:
2823:
2767:
2740:
2613:
2554:
2526:
2516:
2469:
2433:
2349:
2311:
2293:
2288:
2268:
2245:
2216:
2194:
2174:
2164:
2015:
2000:
1980:
1866:
1797:
1783:
1738:
1671:
1666:
1643:
1618:
1586:
1529:
1492:
1469:
1454:
1449:
1434:
1000:
657:, though other mechanisms may also contribute. DNA damage induces activation of
646:
642:
51:
1295:"An N-nitrosating metalloenzyme constructs the pharmacophore of streptozotocin"
831:
Proceedings of the
National Academy of Sciences of the United States of America
20:
3015:
2923:
2918:
2898:
2893:
2888:
2883:
2878:
2848:
2838:
2803:
2798:
2778:
2733:
2721:
2696:
2691:
2681:
2663:
2658:
2648:
2643:
2601:
2589:
2577:
2549:
2536:
2531:
2501:
2464:
2459:
2397:
2392:
2338:
2283:
2235:
2221:
2169:
2156:
2125:
2058:
2047:
2020:
2010:
2005:
1951:
1906:
1901:
1802:
1766:
1698:
1688:
1677:
1661:
1613:
1596:
1572:
1524:
1512:
1464:
1354:
1318:
1228:
1177:
1160:
902:
885:
697:
674:
619:
603:
436:
266:
965:
3030:
3010:
2965:
2955:
2949:
2868:
2813:
2762:
2686:
2676:
2631:
2618:
2559:
2521:
2449:
2387:
2328:
2317:
2273:
2230:
2189:
2183:
2179:
2141:
2068:
2063:
2053:
2025:
1985:
1946:
1921:
1911:
1871:
1517:
1507:
1502:
1497:
1459:
886:"N-acetylcysteine protects memory decline induced by streptozotocin in mice"
626:
555:
1336:
1279:
1236:
1186:
1035:
938:
911:
851:
811:
1140:
1101:
1070:
1008:
973:
884:
Costa M, Bernardi J, Fiuza T, Costa L, BrandΓ£o R, Pereira ME (June 2016).
2939:
2913:
2858:
2626:
2564:
2344:
2240:
2212:
1891:
1728:
870:
563:
559:
246:
1086:"Drugs producing diabetes through damage of the insulin secreting cells"
653:
in the nitrosourea class, it is toxic to cells by causing damage to the
255:
1847:
1748:
1562:
1423:
770:
705:
615:
221:
1487:
717:
691:. The soil sample in which the microbe turned up had been taken from
684:
346:
152:
315:
1293:
Ng TL, Rohac R, Mitchell AJ, Boal AK, Balskus EP (February 2019).
662:
459:
450:
326:
148:
673:
Streptozotocin was originally identified in the late 1950s as an
1165:
The
British Journal of Psychiatry: The Journal of Mental Science
825:
Rossini AA, Like AA, Chick WL, Appel MC, Cahill GF (June 1977).
306:
1369:
654:
371:
677:. The drug was discovered in a strain of the soil microbe
827:"Studies of streptozotocin-induced insulitis and diabetes"
525:
683:
by scientists at the drug company Upjohn (now part of
2755:
2706:
2486:
2479:
2415:
2369:
2302:
2259:
2096:
2081:
1961:
1931:
1856:
1841:
1812:
1708:
1628:
1571:
1554:
1543:
1479:
1432:
1413:
448:
435:
402:
397:
365:
345:
325:
305:
285:
265:
245:
220:
200:
171:
158:
142:
132:
124:
108:
103:
78:
64:
50:
40:
35:
751:responsible for production of Streptozotocin in
234:
1154:
1152:
1150:
209:
1381:
8:
712:investigated streptozotocin's use in cancer
19:
570:and used in medical research to produce an
117:In general: β (Prescription only)
2483:
2093:
1853:
1568:
1551:
1429:
1388:
1374:
1366:
385:
274:
1326:
1176:
901:
860:
850:
735:Recent advancements in understanding the
294:
782:
598:Streptozotocin is approved by the U.S.
499:
479:
381:
254:
185:
56:
18:
792:The Surgical Clinics of North America
354:
334:
7:
91:
1657:ribonucleotide reductase inhibitors
568:cancers of the islets of Langerhans
314:
225:
1823:Ribonucleotide reductase inhibitor
1779:Ribonucleotide reductase inhibitor
14:
1582:Dihydrofolate reductase inhibitor
3093:Alkylating antineoplastic agents
747:In short, the authors found the
420:
414:
27:
890:Chemico-Biological Interactions
507:Key:ZSJLQEPLLKMAKR-GKHCUFPYSA-N
1719:Thymidylate synthase inhibitor
1609:Thymidylate synthase inhibitor
1217:Journal of Neural Transmission
426:
408:
188:2-Deoxy-2-({carbonyl}amino)-Ξ²-
1:
1639:Adenosine deaminase inhibitor
1480:Block microtubule disassembly
1272:10.1016/s0024-3205(00)01005-5
1133:10.1016/S0140-6736(68)91058-1
1063:10.1016/S0140-6736(68)92103-X
804:10.1016/S0039-6109(05)70141-9
761:by oxidative rearrangement.
600:Food and Drug Administration
582:in a large dose, as well as
1001:10.2337/diabetes.43.11.1326
701:was granted in March 1962.
482:CN(C(=O)N1(((O1O)CO)O)O)N=O
3134:
3103:Monosaccharide derivatives
1084:Rerup CC (December 1970).
743:have been made by Balskus
562:in mammals. It is used in
398:Chemical and physical data
3098:IARC Group 2B carcinogens
3043:
2929:Omacetaxine mepesuccinate
2819:Ciltacabtagene autoleucel
2809:Brexucabtagene autoleucel
1319:10.1038/s41586-019-0894-z
1229:10.1007/s00702-015-1394-4
1178:10.1192/bjp.bp.109.067942
903:10.1016/j.cbi.2016.04.026
754:Streptomyces achromogenes
710:National Cancer Institute
680:Streptomyces achromogenes
590:with multiple low doses.
515:
490:
470:
176:
26:
2976:Talimogene laherparepvec
1843:Topoisomerase inhibitors
1762:DNA polymerase inhibitor
966:10.2337/diabetes.47.1.50
649:compound. As with other
2794:Axicabtagene ciloleucel
1398:chemotherapeutic agents
1090:Pharmacological Reviews
2961:Sitimagene ceradenovec
2874:Idecabtagene vicleucel
2439:Methyl aminolevulinate
927:Physiological Research
852:10.1073/pnas.74.6.2485
608:pancreatic islet cells
2450:Porphyrin derivatives
2146:Melphalan flufenamide
1793:Hypomethylating agent
1402:antineoplastic agents
1355:U.S. patent 3,027,300
698:U.S. patent 3,027,300
566:for treating certain
2779:Asparagine depleters
2708:Receptor antagonists
2622:+abiraterone acetate
641:Streptozotocin is a
631:experimental animals
2829:Denileukin diftitox
2729:Retinoid X receptor
2429:Aminolevulinic acid
2251:Triethylenemelamine
2083:Crosslinking of DNA
1814:Deoxyribonucleotide
1753:+gimeracil/oteracil
1311:2019Natur.566...94N
843:1977PNAS...74.2485R
693:Blue Rapids, Kansas
689:Kalamazoo, Michigan
602:(FDA) for treating
138:17β25% (100% if IV)
23:
3070:Never to phase III
1887:Etirinotecan pegol
1024:Antibiotics Annual
3080:
3079:
3039:
3038:
2996:Tigilanol tiglate
2488:Enzyme inhibitors
2411:
2410:
2407:
2406:
2107:Nitrogen mustards
2077:
2076:
1837:
1836:
1539:
1538:
1127:(7574): 895β898.
1057:(7544): 670β671.
995:(11): 1326β1333.
651:alkylating agents
614:due to excessive
533:
532:
461:Interactive image
367:CompTox Dashboard
191:
16:Chemical compound
3125:
3001:Tisagenlecleucel
2773:Arsenic trioxide
2484:
2417:Photosensitizers
2208:Alkyl sulfonates
2122:Cyclophosphamide
2094:
2033:Anthracenediones
1854:
1828:Hydroxycarbamide
1569:
1552:
1430:
1390:
1383:
1376:
1367:
1361:FDA drug details
1357:
1341:
1340:
1330:
1290:
1284:
1283:
1266:(9): 1021β1029.
1255:
1249:
1248:
1214:
1205:
1199:
1198:
1180:
1156:
1145:
1144:
1116:
1110:
1109:
1104:. Archived from
1081:
1075:
1074:
1046:
1040:
1039:
1019:
1013:
1012:
984:
978:
977:
949:
943:
942:
922:
916:
915:
905:
881:
875:
874:
864:
854:
837:(6): 2485β2489.
822:
816:
815:
787:
700:
629:and diabetes on
529:
528:
521:
463:
443:
428:
422:
416:
410:
390:
389:
375:
373:
358:
338:
318:
298:
278:
258:
238:
228:
227:
213:
189:
163:
95:
60:
31:
24:
22:
3133:
3132:
3128:
3127:
3126:
3124:
3123:
3122:
3083:
3082:
3081:
3076:
3075:
3060:Clinical trials
3035:
2756:Other/ungrouped
2751:
2702:
2475:
2455:Porfimer sodium
2403:
2365:
2298:
2255:
2085:
2073:
1957:
1927:
1845:
1833:
1808:
1704:
1624:
1560:
1558:antimetabolites
1556:
1555:DNA precursors/
1547:
1545:DNA replication
1535:
1475:
1445:Vinca alkaloids
1421:
1409:
1394:
1353:
1350:
1345:
1344:
1305:(7742): 94β99.
1292:
1291:
1287:
1257:
1256:
1252:
1212:
1207:
1206:
1202:
1158:
1157:
1148:
1118:
1117:
1113:
1083:
1082:
1078:
1048:
1047:
1043:
1021:
1020:
1016:
986:
985:
981:
951:
950:
946:
924:
923:
919:
883:
882:
878:
824:
823:
819:
789:
788:
784:
779:
767:
741:natural product
733:
696:
671:
639:
596:
588:type 1 diabetes
584:type 2 diabetes
524:
522:
519:(what is this?)
516:
511:
508:
503:
498:
497:
486:
483:
478:
477:
466:
441:
431:
425:
419:
413:
393:
369:
361:
341:
321:
301:
281:
261:
241:
224:
216:
196:
193:
184:
183:
161:
134:Bioavailability
126:Pharmacokinetic
120:
99:
67:
17:
12:
11:
5:
3131:
3129:
3121:
3120:
3115:
3110:
3105:
3100:
3095:
3085:
3084:
3078:
3077:
3074:
3073:
3072:
3071:
3068:
3057:
3051:
3045:
3044:
3041:
3040:
3037:
3036:
3034:
3033:
3028:
3023:
3018:
3013:
3008:
3003:
2998:
2993:
2988:
2983:
2978:
2973:
2968:
2963:
2958:
2953:
2947:
2936:
2931:
2926:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2886:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2821:
2816:
2811:
2806:
2801:
2796:
2791:
2775:
2770:
2765:
2759:
2757:
2753:
2752:
2750:
2749:
2737:
2725:
2712:
2710:
2704:
2703:
2701:
2700:
2694:
2689:
2684:
2679:
2667:
2661:
2656:
2651:
2646:
2635:
2629:
2624:
2616:
2609:PARP inhibitor
2605:
2593:
2581:
2569:
2568:
2567:
2562:
2557:
2552:
2540:
2534:
2529:
2524:
2519:
2505:
2492:
2490:
2481:
2477:
2476:
2474:
2473:
2467:
2462:
2457:
2446:
2441:
2436:
2431:
2425:
2423:
2413:
2412:
2409:
2408:
2405:
2404:
2402:
2401:
2395:
2390:
2385:
2375:
2373:
2367:
2366:
2364:
2363:
2357:
2352:
2341:
2336:
2331:
2326:
2314:
2308:
2306:
2300:
2299:
2297:
2296:
2291:
2286:
2281:
2276:
2271:
2265:
2263:
2261:Platinum-based
2257:
2256:
2254:
2253:
2248:
2243:
2238:
2226:
2225:
2219:
2203:
2202:
2197:
2192:
2187:
2177:
2172:
2160:
2159:
2154:
2149:
2139:
2134:
2128:
2119:
2114:
2102:
2100:
2091:
2079:
2078:
2075:
2074:
2072:
2071:
2066:
2061:
2056:
2051:
2045:
2040:
2029:
2023:
2018:
2013:
2008:
2003:
1998:
1988:
1983:
1976:Anthracyclines
1971:
1969:
1959:
1958:
1956:
1955:
1949:
1937:
1935:
1929:
1928:
1926:
1925:
1919:
1914:
1909:
1904:
1899:
1894:
1889:
1884:
1879:
1874:
1862:
1860:
1851:
1839:
1838:
1835:
1834:
1832:
1831:
1818:
1816:
1810:
1809:
1807:
1806:
1800:
1788:
1787:
1774:
1773:
1757:
1756:
1746:
1741:
1736:
1731:
1726:
1714:
1712:
1706:
1705:
1703:
1702:
1696:
1694:Mercaptopurine
1685:
1680:
1675:
1669:
1664:
1648:
1647:
1634:
1632:
1626:
1625:
1623:
1622:
1616:
1605:
1599:
1594:
1589:
1577:
1575:
1566:
1549:
1541:
1540:
1537:
1536:
1534:
1533:
1521:
1515:
1510:
1505:
1500:
1495:
1483:
1481:
1477:
1476:
1474:
1473:
1467:
1462:
1457:
1452:
1440:
1438:
1427:
1411:
1410:
1396:Intracellular
1395:
1393:
1392:
1385:
1378:
1370:
1364:
1363:
1358:
1349:
1348:External links
1346:
1343:
1342:
1285:
1250:
1223:(4): 577β592.
1200:
1146:
1111:
1108:on 2012-07-12.
1096:(4): 485β518.
1076:
1041:
1014:
979:
944:
933:(6): 537β546.
917:
876:
817:
798:(3): 527β542.
781:
780:
778:
775:
774:
773:
766:
763:
732:
729:
670:
667:
638:
635:
606:cancer of the
595:
592:
536:Streptozotocin
531:
530:
513:
512:
510:
509:
506:
504:
501:
493:
492:
491:
488:
487:
485:
484:
481:
473:
472:
471:
468:
467:
465:
464:
456:
454:
446:
445:
439:
433:
432:
429:
423:
417:
411:
406:
400:
399:
395:
394:
392:
391:
378:
376:
363:
362:
360:
359:
351:
349:
343:
342:
340:
339:
331:
329:
323:
322:
320:
319:
311:
309:
303:
302:
300:
299:
291:
289:
283:
282:
280:
279:
271:
269:
263:
262:
260:
259:
251:
249:
243:
242:
240:
239:
231:
229:
218:
217:
215:
214:
206:
204:
198:
197:
195:
194:
192:-glucopyranose
187:
179:
178:
177:
174:
173:
169:
168:
165:
156:
155:
146:
140:
139:
136:
130:
129:
122:
121:
119:
118:
114:
112:
106:
105:
101:
100:
98:
97:
84:
82:
76:
75:
70:
68:administration
62:
61:
54:
48:
47:
44:
38:
37:
33:
32:
21:Streptozotocin
15:
13:
10:
9:
6:
4:
3:
2:
3130:
3119:
3116:
3114:
3111:
3109:
3106:
3104:
3101:
3099:
3096:
3094:
3091:
3090:
3088:
3069:
3067:
3064:
3063:
3061:
3058:
3055:
3052:
3050:
3047:
3046:
3042:
3032:
3029:
3027:
3024:
3022:
3019:
3017:
3014:
3012:
3009:
3007:
3004:
3002:
2999:
2997:
2994:
2992:
2989:
2987:
2984:
2982:
2979:
2977:
2974:
2972:
2969:
2967:
2964:
2962:
2959:
2957:
2954:
2951:
2948:
2946:
2942:
2941:
2937:
2935:
2932:
2930:
2927:
2925:
2922:
2920:
2917:
2915:
2912:
2910:
2907:
2905:
2904:Lurbinectedin
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2880:
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2789:
2785:
2781:
2780:
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2760:
2758:
2754:
2747:
2743:
2742:
2738:
2735:
2731:
2730:
2726:
2723:
2719:
2718:
2714:
2713:
2711:
2709:
2705:
2698:
2695:
2693:
2690:
2688:
2685:
2683:
2680:
2678:
2674:
2672:
2668:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2641:
2640:
2636:
2633:
2630:
2628:
2625:
2623:
2620:
2617:
2615:
2611:
2610:
2606:
2603:
2599:
2598:
2594:
2591:
2587:
2586:
2582:
2579:
2575:
2574:
2570:
2566:
2563:
2561:
2558:
2556:
2553:
2551:
2548:
2547:
2546:
2545:
2541:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2514:
2513:
2510:
2506:
2503:
2499:
2498:
2494:
2493:
2491:
2489:
2485:
2482:
2478:
2471:
2468:
2466:
2463:
2461:
2458:
2456:
2452:
2451:
2447:
2445:
2442:
2440:
2437:
2435:
2432:
2430:
2427:
2426:
2424:
2422:
2418:
2414:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2380:
2377:
2376:
2374:
2372:
2371:Intercalation
2368:
2361:
2358:
2356:
2353:
2351:
2347:
2346:
2342:
2340:
2337:
2335:
2332:
2330:
2327:
2324:
2320:
2319:
2315:
2313:
2310:
2309:
2307:
2305:
2301:
2295:
2292:
2290:
2287:
2285:
2282:
2280:
2279:Dicycloplatin
2277:
2275:
2272:
2270:
2267:
2266:
2264:
2262:
2258:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2228:
2227:
2223:
2220:
2218:
2214:
2211:
2209:
2205:
2204:
2201:
2198:
2196:
2193:
2191:
2188:
2185:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2162:
2161:
2158:
2155:
2153:
2152:Prednimustine
2150:
2147:
2143:
2140:
2138:
2135:
2132:
2129:
2127:
2123:
2120:
2118:
2115:
2113:
2110:
2108:
2104:
2103:
2101:
2099:
2095:
2092:
2089:
2084:
2080:
2070:
2067:
2065:
2062:
2060:
2057:
2055:
2052:
2049:
2046:
2044:
2041:
2039:
2035:
2034:
2030:
2027:
2024:
2022:
2019:
2017:
2014:
2012:
2009:
2007:
2004:
2002:
1999:
1996:
1992:
1989:
1987:
1984:
1982:
1978:
1977:
1973:
1972:
1970:
1968:
1967:Intercalation
1964:
1960:
1953:
1950:
1948:
1944:
1943:
1939:
1938:
1936:
1934:
1930:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1885:
1883:
1880:
1878:
1875:
1873:
1869:
1868:
1864:
1863:
1861:
1859:
1855:
1852:
1849:
1844:
1840:
1829:
1825:
1824:
1820:
1819:
1817:
1815:
1811:
1804:
1801:
1799:
1795:
1794:
1790:
1789:
1785:
1781:
1780:
1776:
1775:
1771:
1770:+daunorubicin
1768:
1764:
1763:
1759:
1758:
1754:
1750:
1747:
1745:
1742:
1740:
1737:
1735:
1734:Doxifluridine
1732:
1730:
1727:
1725:
1721:
1720:
1716:
1715:
1713:
1711:
1707:
1700:
1697:
1695:
1691:
1690:
1686:
1684:
1683:Rabacfosadine
1681:
1679:
1676:
1673:
1670:
1668:
1665:
1663:
1659:
1658:
1654:
1650:
1649:
1645:
1641:
1640:
1636:
1635:
1633:
1631:
1627:
1620:
1617:
1615:
1611:
1610:
1606:
1603:
1600:
1598:
1595:
1593:
1590:
1588:
1584:
1583:
1579:
1578:
1576:
1574:
1570:
1567:
1564:
1559:
1553:
1550:
1546:
1542:
1531:
1527:
1526:
1522:
1519:
1516:
1514:
1511:
1509:
1506:
1504:
1501:
1499:
1496:
1494:
1490:
1489:
1485:
1484:
1482:
1478:
1471:
1468:
1466:
1463:
1461:
1458:
1456:
1453:
1451:
1447:
1446:
1442:
1441:
1439:
1436:
1431:
1428:
1425:
1420:
1416:
1412:
1407:
1403:
1399:
1391:
1386:
1384:
1379:
1377:
1372:
1371:
1368:
1362:
1359:
1356:
1352:
1351:
1347:
1338:
1334:
1329:
1324:
1320:
1316:
1312:
1308:
1304:
1300:
1296:
1289:
1286:
1281:
1277:
1273:
1269:
1265:
1261:
1260:Life Sciences
1254:
1251:
1246:
1242:
1238:
1234:
1230:
1226:
1222:
1218:
1211:
1204:
1201:
1196:
1192:
1188:
1184:
1179:
1174:
1170:
1166:
1162:
1155:
1153:
1151:
1147:
1142:
1138:
1134:
1130:
1126:
1122:
1115:
1112:
1107:
1103:
1099:
1095:
1091:
1087:
1080:
1077:
1072:
1068:
1064:
1060:
1056:
1052:
1045:
1042:
1037:
1033:
1029:
1025:
1018:
1015:
1010:
1006:
1002:
998:
994:
990:
983:
980:
975:
971:
967:
963:
959:
955:
948:
945:
940:
936:
932:
928:
921:
918:
913:
909:
904:
899:
895:
891:
887:
880:
877:
872:
868:
863:
858:
853:
848:
844:
840:
836:
832:
828:
821:
818:
813:
809:
805:
801:
797:
793:
786:
783:
776:
772:
769:
768:
764:
762:
760:
759:pharmacophore
756:
755:
750:
746:
742:
738:
730:
728:
725:
721:
719:
715:
711:
707:
702:
699:
694:
690:
686:
682:
681:
676:
668:
666:
664:
660:
656:
652:
648:
644:
636:
634:
632:
628:
623:
621:
618:secretion by
617:
613:
609:
605:
601:
593:
591:
589:
585:
581:
577:
576:hyperglycemia
573:
569:
565:
561:
557:
553:
549:
545:
541:
537:
527:
520:
514:
505:
500:
496:
489:
480:
476:
469:
462:
458:
457:
455:
452:
447:
440:
438:
434:
407:
405:
401:
396:
388:
384:
383:DTXSID2021282
380:
379:
377:
368:
364:
357:
353:
352:
350:
348:
344:
337:
333:
332:
330:
328:
324:
317:
313:
312:
310:
308:
304:
297:
293:
292:
290:
288:
284:
277:
273:
272:
270:
268:
264:
257:
253:
252:
250:
248:
244:
237:
233:
232:
230:
223:
219:
212:
208:
207:
205:
203:
199:
186:
182:
175:
170:
167:35β40 minutes
166:
164:
157:
154:
150:
147:
145:
141:
137:
135:
131:
127:
123:
116:
115:
113:
111:
107:
102:
94:
89:
86:
85:
83:
81:
77:
74:
71:
69:
63:
59:
55:
53:
49:
45:
43:
39:
36:Clinical data
34:
30:
25:
3113:Nitrosoureas
3108:Nitrosamines
2981:Tazemetostat
2945:Alitretinoin
2938:
2864:Estramustine
2844:Elsamitrucin
2834:Eflornithine
2788:Pegaspargase
2784:Asparaginase
2777:
2746:Testolactone
2739:
2727:
2715:
2669:
2654:Panobinostat
2637:
2607:
2595:
2583:
2571:
2542:
2507:
2495:
2448:
2444:Padeliporfin
2383:Dactinomycin
2379:Streptomyces
2360:Temozolomide
2355:Mitozolomide
2343:
2334:Mitobronitol
2323:Procarbazine
2316:
2304:Nonclassical
2229:
2206:
2200:Streptozocin
2199:
2165:Nitrosoureas
2163:
2137:Chlorambucil
2131:Trofosfamide
2117:Chlormethine
2112:Bendamustine
2105:
2043:Mitoxantrone
2038:Losoxantrone
2031:
1991:Daunorubicin
1974:
1940:
1877:Camptothecin
1865:
1821:
1791:
1777:
1760:
1744:Fluorouracil
1724:Capecitabine
1717:
1687:
1651:
1637:
1607:
1602:Pralatrexate
1592:Methotrexate
1580:
1523:
1486:
1443:
1302:
1298:
1288:
1263:
1259:
1253:
1220:
1216:
1203:
1171:(1): 36β40.
1168:
1164:
1124:
1120:
1114:
1106:the original
1093:
1089:
1079:
1054:
1050:
1044:
1027:
1023:
1017:
992:
988:
982:
960:(1): 50β56.
957:
953:
947:
930:
926:
920:
893:
889:
879:
834:
830:
820:
795:
791:
785:
752:
749:gene cluster
744:
737:biosynthesis
734:
731:Biosynthesis
726:
722:
714:chemotherapy
703:
678:
672:
640:
624:
612:hypoglycemia
597:
572:animal model
551:
540:streptozocin
539:
535:
534:
523:
517:
356:ChEMBL450214
160:Elimination
110:Legal status
104:Legal status
3056:from market
3026:Vorasidenib
3006:Trabectedin
2991:Tiazofurine
2986:Tebentafusp
2971:Tagraxofusp
2934:Plitidepsin
2909:Mitoguazone
2854:Epacadostat
2824:Demecolcine
2768:Aflibercept
2741:Sex steroid
2614:Fuzuloparib
2555:Carfilzomib
2527:Palbociclib
2517:Abemaciclib
2470:Verteporfin
2434:Efaproxiral
2350:Dacarbazine
2312:Altretamine
2294:Satraplatin
2289:Oxaliplatin
2269:Carboplatin
2246:Triaziquone
2217:Mannosulfan
2195:Ranimustine
2175:Fotemustine
2016:Pirarubicin
2001:Doxorubicin
1995:+cytarabine
1981:Aclarubicin
1942:Podophyllum
1867:Camptotheca
1798:Azacitidine
1784:Gemcitabine
1739:Floxuridine
1672:Fludarabine
1667:Clofarabine
1653:Halogenated
1644:Pentostatin
1619:Raltitrexed
1587:Aminopterin
1530:Ixabepilone
1525:Epothilones
1493:Cabazitaxel
1470:Vinorelbine
1455:Vincristine
1450:Vinblastine
1435:microtubule
1030:: 230β235.
647:nitrosourea
643:glucosamine
620:insulinomas
580:Alzheimer's
444: gΒ·mol
172:Identifiers
73:Intravenous
52:MedlinePlus
42:Trade names
3087:Categories
3021:Verdinexor
3016:Venetoclax
2924:Oblimersen
2919:Navitoclax
2899:Lucanthone
2894:Lonidamine
2889:Lifileucel
2884:Ivosidenib
2879:Imetelstat
2849:Enasidenib
2839:Elesclomol
2804:Bexarotene
2799:Belzutifan
2734:Bexarotene
2722:Atrasentan
2697:Umbralisib
2692:Idelalisib
2682:Copanlisib
2664:Vorinostat
2659:Romidepsin
2649:Entinostat
2644:Belinostat
2602:Masoprocol
2590:Tiazofurin
2578:Anagrelide
2550:Bortezomib
2537:Seliciclib
2532:Ribociclib
2512:inhibitors
2502:Tipifarnib
2465:Temoporfin
2460:Talaporfin
2398:Plicamycin
2393:Mitomycins
2339:Pipobroman
2318:Hydrazines
2284:Nedaplatin
2236:Carboquone
2231:Aziridines
2222:Treosulfan
2170:Carmustine
2157:Uramustine
2126:Ifosfamide
2098:Alkylating
2059:Bisantrene
2048:Pixantrone
2021:Valrubicin
2011:Idarubicin
2006:Epirubicin
1952:Teniposide
1907:Lurtotecan
1902:Irinotecan
1803:Decitabine
1767:Cytarabine
1710:Pyrimidine
1699:Tioguanine
1689:Thiopurine
1678:Nelarabine
1662:Cladribine
1614:Pemetrexed
1597:Pemetrexed
1573:Folic acid
1513:Paclitaxel
1465:Vinflunine
777:References
675:antibiotic
604:metastatic
556:beta cells
449:3D model (
437:Molar mass
336:CHEBI:9288
296:5W494URQ81
267:ChemSpider
211:18883-66-4
202:CAS Number
181:IUPAC name
144:Metabolism
3066:Phase III
3054:Withdrawn
3031:Vosaroxin
3011:Veliparib
2966:Sotorasib
2956:Selinexor
2950:Tretinoin
2940:Retinoids
2869:Glasdegib
2814:Celecoxib
2763:Adagrasib
2687:Duvelisib
2677:Alpelisib
2632:Rucaparib
2619:Niraparib
2560:Oprozomib
2522:Alvocidib
2388:Bleomycin
2345:Triazenes
2329:Etoglucid
2274:Cisplatin
2190:Nimustine
2184:Semustine
2180:Lomustine
2142:Melphalan
2069:Menogaril
2064:Crisnatol
2054:Amsacrine
2026:Zorubicin
1986:Amrubicin
1947:Etoposide
1922:Topotecan
1917:Silatecan
1912:Rubitecan
1897:Gimatecan
1882:Cositecan
1872:Belotecan
1548:inhibitor
1518:Tesetaxel
1508:Ortataxel
1503:Larotaxel
1498:Docetaxel
1460:Vindesine
896:: 10β17.
637:Mechanism
627:insulitis
162:half-life
66:Routes of
2914:Mitotane
2859:Eribulin
2627:Olaparib
2565:Ixazomib
2241:Thiotepa
2213:Busulfan
1892:Exatecan
1729:Carmofur
1437:assembly
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989:Diabetes
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912:27087133
812:11459269
765:See also
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564:medicine
560:pancreas
526:(verify)
247:DrugBank
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1848:S phase
1749:Tegafur
1563:S phase
1488:Taxanes
1424:M phase
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1307:Bibcode
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616:insulin
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495:InChI
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