271:
248:
29:
741:
465:, but is less potential against AChE from mammalian origin. This might come from differences in the configuration of active center between schistosome and mammalian AChE enzymes.
41:
401:
749:
357:
343:
714:
Schutt AJ, Dalton RJ, Kovach JS, Moertel CG, O'Connell MJ (June 1983). "Phase II study of hycanthone in patients with advanced colorectal carcinoma".
1516:
781:
1249:
1065:
916:
1472:
663:
377:
646:
Teoh NC, Chitturi S, Farrell GC (2010). "Chapter 86: Liver
Disease Caused by Drugs". In Feldman M, Friedman LS, Brandt LJ (eds.).
1296:
1211:
1531:
385:
InChI=1S/C20H24N2O2S/c1-3-22(4-2)12-11-21-16-10-9-14(13-23)20-18(16)19(24)15-7-5-6-8-17(15)25-20/h5-10,21,23H,3-4,11-13H2,1-2H3
65:
867:
1521:
469:
147:
1489:
1413:
774:
227:
815:
759:
611:
Hillman GR, Senft AW (September 1975). "Anticholinergic properties of the antischistosomal drug hycanthone".
1477:
266:
1526:
767:
1278:
567:
216:
506:
Phase II Chemotherapy with
Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas (Completed)
1421:
1305:
456:
1454:
1142:
679:
Stine JG, Lewis JH (2013). "Hepatotoxicity of
Antibiotics: A Review and Update for the Clinician".
461:
243:
82:
1371:
1005:
543:
1342:
1333:
1338:
723:
696:
659:
628:
196:
1316:
1284:
806:
742:"Phase II Chemotherapy with Hycanthone Mesylate and Flagyl for Advanced Malignant Lymphomas"
688:
651:
620:
283:
156:
1439:
1148:
1088:
876:
855:
829:
519:
422:
136:
91:
270:
247:
1483:
1449:
1407:
1194:
1074:
907:
655:
479:
444:
1510:
1215:
1168:
1102:
1030:
989:
849:
790:
555:
259:
593:
1245:
1199:
1189:
1184:
1122:
1116:
1061:
958:
912:
802:
798:
794:
503:
Phase II Study of
Chemotherapy with Hycanthone for Advanced Colorectal Carcinoma.
116:
1393:
1179:
1174:
1080:
1036:
922:
882:
491:
1434:
1385:
1366:
1274:
1268:
1260:
1255:
1235:
1224:
1108:
1094:
1010:
969:
950:
692:
624:
531:
426:
319:
127:
1399:
1240:
1230:
1055:
984:
936:
901:
824:
437:
and death. This agent also intercalates into DNA and inhibits RNA synthesis
434:
700:
20:
727:
632:
1444:
1379:
1328:
1311:
977:
944:
474:
439:
430:
1427:
1323:
1159:
1021:
840:
650:. Vol. 2 (Ninth ed.). Saunders Elsevier. pp. 1413–1446.
102:
28:
930:
207:
176:
342:
333:
187:
167:
763:
73:
1-(2-Diethylaminoethylamino)-4-(hydroxymethyl)-9-thioxanthenone
478:. A growing body of evidence has shown that hycathone has an
648:
Sleisenger and
Fordtran's Gastrointestinal and Liver Disease
232:
408:
613:
The
American Journal of Tropical Medicine and Hygiene
455:
Hycanthone is shown to be an effective inhibitor of
425:
approved by the FDA in 1975. It is a metabolite of
1354:
1295:
1210:
1157:
1141:
1047:
1019:
1004:
893:
866:
838:
823:
814:
331:
318:
282:
277:
258:
226:
206:
186:
166:
146:
126:
101:
81:
56:
40:
35:
115:
90:
537:Soluble in ethanol, methanol, DMSO, and water
775:
8:
365:CCN(CC)CCNC1=C2C(=C(C=C1)CO)SC3=CC=CC=C3C2=O
19:
1154:
1016:
835:
820:
782:
768:
760:
269:
246:
135:
27:
155:
514:
585:
382:
362:
242:
70:
260:
18:
215:
195:
7:
472:into DNA and inhibit RNA synthesis
175:
106:
656:10.1016/B978-1-4160-6189-2.00086-X
14:
494:, causing hepatocellular injury.
1212:Glutamate-gated chloride channel
300:
294:
490:Hycanthone is a dose-dependent
390:Key:MFZWMTSUNYWVBU-UHFFFAOYSA-N
1517:Drugs not assigned an ATC code
746:U.S. National Cancer Institute
312:
306:
288:
1:
433:nerve function, resulting in
429:. Hycanthone interferes with
549:233, 258, 329, 438 nm
1548:
1250:+esafoxolaner/praziquantel
1066:+esafoxolaner/eprinomectin
917:+esafoxolaner/eprinomectin
451:Anti-schistosomal activity
278:Chemical and physical data
1467:
816:Antiplatyhelmintic agents
693:10.1016/j.cld.2013.07.008
625:10.4269/ajtmh.1975.24.827
398:
373:
353:
61:
26:
716:Cancer Treatment Reports
681:Clinics in Liver Disease
468:Hycanthone is shown to
1532:Diethylamino compounds
598:NCI Cancer Dictionary
1522:Antiparasitic agents
1422:naphthalenesulfonate
1306:tetrahydropyrimidine
1143:Antinematodal agents
752:on 13 February 2015.
457:acetylcholinesterase
443:and shows potential
1455:Tetrachloroethylene
511:Physical properties
462:Schistosoma mansoni
23:
1494:Never to phase III
1372:Diethylcarbamazine
544:Absorption maximum
1504:
1503:
1463:
1462:
1137:
1136:
1133:
1132:
1000:
999:
665:978-1-4160-6189-2
577:
576:
416:
415:
344:Interactive image
228:CompTox Dashboard
16:Chemical compound
1539:
1317:pyrantel pamoate
1285:Milbemycin oxime
1155:
1149:macrofilaricides
1017:
836:
830:schistosomicides
821:
784:
777:
770:
761:
754:
753:
748:. Archived from
738:
732:
731:
711:
705:
704:
676:
670:
669:
643:
637:
636:
608:
602:
601:
590:
561:173-176 °C
515:
412:
411:
404:
346:
326:
314:
308:
302:
296:
290:
273:
262:
251:
250:
236:
234:
219:
199:
179:
159:
139:
119:
109:
108:
94:
31:
24:
22:
1547:
1546:
1542:
1541:
1540:
1538:
1537:
1536:
1507:
1506:
1505:
1500:
1499:
1484:Clinical trials
1459:
1440:Hexylresorcinol
1350:
1291:
1206:
1147:
1145:
1129:
1043:
1008:
996:
889:
877:phosphonic acid
862:
856:Triclabendazole
827:
825:Antitrematodals
810:
788:
758:
757:
740:
739:
735:
713:
712:
708:
678:
677:
673:
666:
645:
644:
640:
610:
609:
605:
592:
591:
587:
582:
513:
500:
498:Clinical trials
488:
453:
423:schistosomicide
407:
405:
402:(what is this?)
399:
394:
391:
386:
381:
380:
369:
366:
361:
360:
349:
324:
311:
305:
299:
293:
254:
230:
222:
202:
182:
162:
142:
122:
105:
97:
77:
74:
69:
68:
52:
17:
12:
11:
5:
1545:
1543:
1535:
1534:
1529:
1524:
1519:
1509:
1508:
1502:
1501:
1498:
1497:
1496:
1495:
1492:
1481:
1475:
1469:
1468:
1465:
1464:
1461:
1460:
1458:
1457:
1452:
1450:Tribendimidine
1447:
1442:
1437:
1432:
1431:
1430:
1418:
1417:
1416:
1408:benzylammonium
1404:
1403:
1402:
1390:
1389:
1388:
1376:
1375:
1374:
1369:
1358:
1356:
1352:
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1347:
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1336:
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1243:
1238:
1233:
1220:
1218:
1208:
1207:
1205:
1204:
1203:
1202:
1197:
1195:Ciclobendazole
1192:
1187:
1182:
1177:
1164:
1162:
1152:
1139:
1138:
1135:
1134:
1131:
1130:
1128:
1127:
1126:
1125:
1113:
1112:
1111:
1099:
1098:
1097:
1085:
1084:
1083:
1075:salicylanilide
1071:
1070:
1069:
1051:
1049:
1045:
1044:
1042:
1041:
1040:
1039:
1026:
1024:
1014:
1002:
1001:
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997:
995:
994:
993:
992:
987:
974:
973:
972:
967:
955:
954:
953:
941:
940:
939:
927:
926:
925:
920:
910:
908:Arpraziquantel
897:
895:
891:
890:
888:
887:
886:
885:
872:
870:
868:AChE inhibitor
864:
863:
861:
860:
859:
858:
845:
843:
833:
818:
812:
811:
791:Antiparasitics
789:
787:
786:
779:
772:
764:
756:
755:
733:
706:
687:(4): 609–642.
671:
664:
638:
603:
584:
583:
581:
578:
575:
574:
571:
563:
562:
559:
551:
550:
547:
539:
538:
535:
527:
526:
523:
520:Physical state
512:
509:
508:
507:
504:
499:
496:
487:
484:
480:antineoplastic
452:
449:
445:antineoplastic
414:
413:
396:
395:
393:
392:
389:
387:
384:
376:
375:
374:
371:
370:
368:
367:
364:
356:
355:
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329:
328:
322:
316:
315:
309:
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264:
256:
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239:
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212:
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192:
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184:
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144:
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132:
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121:
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112:
110:
99:
98:
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87:
85:
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78:
76:
75:
72:
64:
63:
62:
59:
58:
54:
53:
51:
50:
46:
44:
38:
37:
33:
32:
15:
13:
10:
9:
6:
4:
3:
2:
1544:
1533:
1530:
1528:
1527:Thioxanthones
1525:
1523:
1520:
1518:
1515:
1514:
1512:
1493:
1491:
1488:
1487:
1485:
1482:
1479:
1476:
1474:
1471:
1470:
1466:
1456:
1453:
1451:
1448:
1446:
1443:
1441:
1438:
1436:
1433:
1429:
1426:
1425:
1424:
1423:
1419:
1415:
1412:
1411:
1410:
1409:
1405:
1401:
1398:
1397:
1396:
1395:
1391:
1387:
1384:
1383:
1382:
1381:
1377:
1373:
1370:
1368:
1365:
1364:
1363:
1360:
1359:
1357:
1355:Other/unknown
1353:
1344:
1340:
1337:
1335:
1332:
1330:
1327:
1325:
1322:
1318:
1315:
1314:
1313:
1310:
1309:
1308:
1307:
1303:
1302:
1300:
1298:
1294:
1286:
1283:
1280:
1276:
1273:
1272:
1271:
1270:
1266:
1262:
1259:
1257:
1254:
1251:
1247:
1244:
1242:
1239:
1237:
1234:
1232:
1229:
1228:
1227:
1226:
1222:
1221:
1219:
1217:
1216:GABA receptor
1213:
1209:
1201:
1198:
1196:
1193:
1191:
1188:
1186:
1183:
1181:
1178:
1176:
1173:
1172:
1171:
1170:
1169:benzimidazole
1166:
1165:
1163:
1161:
1156:
1153:
1150:
1144:
1140:
1124:
1121:
1120:
1119:
1118:
1114:
1110:
1107:
1106:
1105:
1104:
1103:butyrophenone
1100:
1096:
1093:
1092:
1091:
1090:
1089:aminoacridine
1086:
1082:
1079:
1078:
1077:
1076:
1072:
1067:
1063:
1060:
1059:
1058:
1057:
1053:
1052:
1050:
1048:Other/unknown
1046:
1038:
1035:
1034:
1033:
1032:
1031:benzimidazole
1028:
1027:
1025:
1023:
1018:
1015:
1012:
1007:
1006:Anticestodals
1003:
991:
990:Tartar emetic
988:
986:
983:
982:
981:
979:
975:
971:
968:
966:
963:
962:
961:
960:
956:
952:
949:
948:
947:
946:
942:
938:
935:
934:
933:
932:
928:
924:
921:
918:
914:
911:
909:
906:
905:
904:
903:
899:
898:
896:
894:Other/unknown
892:
884:
881:
880:
879:
878:
874:
873:
871:
869:
865:
857:
854:
853:
852:
851:
850:benzimidazole
847:
846:
844:
842:
837:
834:
831:
826:
822:
819:
817:
813:
808:
804:
800:
796:
795:Anthelmintics
792:
785:
780:
778:
773:
771:
766:
765:
762:
751:
747:
743:
737:
734:
729:
725:
721:
717:
710:
707:
702:
698:
694:
690:
686:
682:
675:
672:
667:
661:
657:
653:
649:
642:
639:
634:
630:
626:
622:
619:(5): 827–34.
618:
614:
607:
604:
599:
595:
589:
586:
579:
572:
570:
569:
565:
564:
560:
558:
557:
556:Melting point
553:
552:
548:
546:
545:
541:
540:
536:
534:
533:
529:
528:
524:
522:
521:
517:
516:
510:
505:
502:
501:
497:
495:
493:
485:
483:
481:
477:
476:
471:
466:
464:
463:
458:
450:
448:
446:
442:
441:
436:
432:
428:
424:
420:
410:
403:
397:
388:
383:
379:
372:
363:
359:
352:
345:
341:
340:
338:
335:
330:
323:
321:
317:
287:
285:
281:
276:
272:
268:
265:
263:
261:ECHA InfoCard
257:
249:
245:
244:DTXSID9023128
241:
240:
238:
229:
225:
218:
214:
213:
211:
209:
205:
198:
194:
193:
191:
189:
185:
178:
174:
173:
171:
169:
165:
158:
154:
153:
151:
149:
145:
138:
134:
133:
131:
129:
125:
118:
114:
113:
111:
104:
100:
93:
89:
88:
86:
84:
80:
71:
67:
60:
55:
48:
47:
45:
43:
39:
36:Clinical data
34:
30:
25:
1420:
1406:
1392:
1378:
1361:
1304:
1267:
1246:Eprinomectin
1223:
1200:Flubendazole
1190:Fenbendazole
1185:Tiabendazole
1167:
1123:Dichlorophen
1117:chlorophenol
1115:
1101:
1087:
1073:
1062:Praziquantel
1054:
1029:
976:
964:
959:thioxanthone
957:
943:
929:
913:Praziquantel
900:
875:
848:
803:endectocides
750:the original
745:
736:
722:(6): 593–4.
719:
715:
709:
684:
680:
674:
647:
641:
616:
612:
606:
597:
594:"hycanthone"
588:
566:
554:
542:
530:
518:
489:
473:
467:
460:
459:(AChE) from
454:
438:
418:
417:
406:
400:
1480:from market
1394:quinolinium
1279:+fluralaner
1269:milbemycins
1225:avermectins
1180:Albendazole
1175:Mebendazole
1081:Niclosamide
1037:Albendazole
1011:taeniacides
923:Oxamniquine
883:Metrifonate
492:hepatotoxin
470:intercalate
327: g·mol
267:100.019.512
217:ChEMBL22077
197:CHEBI:52768
57:Identifiers
1511:Categories
1435:Ascaridole
1386:Levamisole
1367:Piperazine
1362:piperazine
1275:Moxidectin
1261:Selamectin
1256:Ivermectin
1236:Doramectin
1146:(including
1109:Desaspidin
1095:Quinacrine
970:Lucanthone
965:Hycanthone
951:Niridazole
580:References
532:Solubility
482:activity.
447:activity.
427:lucanthone
419:Hycanthone
332:3D model (
320:Molar mass
157:2BXX5EVN2A
128:ChemSpider
83:CAS Number
66:IUPAC name
21:Hycanthone
1490:Phase III
1478:Withdrawn
1414:Bephenium
1400:Pyrvinium
1343:felsantel
1334:Carbantel
1241:Emamectin
1231:Abamectin
1056:quinoline
985:Stibophen
980:compounds
937:Bithionol
902:quinoline
435:paralysis
92:3105-97-3
1445:Santonin
1380:thiazole
1339:Febantel
1329:Morantel
1312:Pyrantel
978:antimony
945:thiazole
793: –
701:24099021
486:Toxicity
475:in vitro
440:in vitro
431:parasite
409:(verify)
42:ATC code
1428:Suramin
1324:Oxantel
1160:tubulin
1022:tubulin
841:tubulin
728:6861166
633:1190369
421:is the
284:Formula
103:PubChem
1473:WHO-EM
1158:Binds
1020:Binds
931:phenol
839:Binds
801:) and
726:
699:
662:
631:
525:Solid
358:SMILES
325:356.48
208:ChEMBL
177:D00541
1341:(aka
573:3.74
378:InChI
334:JSmol
188:ChEBI
1297:NMDA
807:QP54
724:PMID
697:PMID
660:ISBN
629:PMID
568:logP
168:KEGG
148:UNII
137:3508
117:3634
49:none
799:P02
689:doi
652:doi
621:doi
233:EPA
107:CID
1513::
1486::
1214:,
744:.
720:67
718:.
695:.
685:17
683:.
658:.
627:.
617:24
615:.
596:.
298:24
292:20
1345:)
1281:)
1277:(
1252:)
1248:(
1151:)
1068:)
1064:(
1013:)
1009:(
919:)
915:(
832:)
828:(
809:)
805:(
797:(
783:e
776:t
769:v
730:.
703:.
691::
668:.
654::
635:.
623::
600:.
336:)
313:S
310:2
307:O
304:2
301:N
295:H
289:C
235:)
231:(
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