764:. The development of AZD-0837 has been discontinued. Due to a limitation identified in long-term stability of the extended-release AZD-0837 drug product, a follow-up study from ASSURE on stroke prevention in patients with non-valvular atrial fibrillation, was prematurely closed in 2010 after 2 years. There was also a numerically higher mortality against warfarin. In a Phase 2 trial for AF the mean serum creatinine concentration increased by about 10% from baseline in patients treated with AZD-0837, which returned to baseline after cessation of therapy.
409:
650:
2560:
40:
2570:
2596:
1128:"Long-term treatment with the oral direct thrombin inhibitor AZD0837, compared to Vitamin-K antagonists, as stroke prevention in patients with non-valvular atrial fibrillation and one or more risk factors for stroke and systemic embolic events. A 5-year follow-up study study"
1192:"Oral direct thrombin inhibitor AZD0837 for the prevention of stroke and systemic embolism in patients with non-valvular atrial fibrillation: a randomized dose-guiding, safety, and tolerability study of four doses of AZD0837 vs. vitamin K antagonists"
596:(liver damage) during trials, and discontinue its distribution in countries where the drug had been approved (Germany, Portugal, Sweden, Finland, Norway, Iceland, Austria, Denmark, France, Switzerland, Argentina and Brazil).
482:
745:
to reject an initial application for approval in 2004. The further development was discontinued in 2006 following reports of hepatotoxicity. Subsequent analysis of Phase 2 clinical study data using
524:
InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1
899:"A randomized, controlled, dose-guiding study of the oral direct thrombin inhibitor ximelagatran compared with standard therapy for the treatment of acute deep vein thrombosis: THRIVE I"
697:
An advantage, according to early reports by its manufacturer, was that it could be taken orally without any monitoring of its anticoagulant properties. This would have set it apart from
1127:
753:
levels observed in Phase 3 clinical studies could have been predicted; if this had been known at the time, it might have affected decisions on future development of the compound.
96:
540:
1079:
Ahrens I, Peter K, Lip GY, Bode C (June 2012). "Development and clinical applications of novel oral anticoagulants. Part II. Drugs under clinical investigation".
760:, was developed by AstraZeneca for similar indications. It is a prodrug of a potent, competitive, reversible inhibitor of free and fibrin-bound thrombin called
2286:
496:
2038:
1276:
1368:
2471:
2636:
2208:
2152:
1135:
825:
694:
such as stroke. The efficacy of ximelagatran for these indications had been well documented, except for non valvular atrial fibrillation.
2616:
2341:
2326:
1523:
742:
516:
1319:
2133:
1541:
1514:
1254:
718:
204:
126:
2441:
1468:
1106:
706:
2514:
1269:
897:
Eriksson H, Wåhlander K, Gustafsson D, Welin LT, Frison L, Schulman S, et al. (THRIVE Investigators) (January 2003).
1752:
328:
2169:
1843:
1563:
710:
585:
388:
737:
Ximelagatran was generally well tolerated in the trial populations, but a small proportion (5–6%) developed elevated
948:"Comparison of ximelagatran with warfarin for the prevention of venous thromboembolism after total knee replacement"
2586:
1036:
Southworth H (July 2014). "Predicting potential liver toxicity from phase 2 data: a case study with ximelagatran".
2201:
1925:
1899:
1891:
605:
2621:
1262:
277:
2509:
2157:
80:
2573:
608:, was the first member of this class that can be taken orally. It acts solely by inhibiting the actions of
2545:
2461:
2456:
2351:
1506:
1430:
683:
377:
2631:
2416:
2281:
2034:
626:
to the active agent melagatran. This conversion takes place in the liver and many other tissues through
268:
946:
Francis CW, Berkowitz SD, Comp PC, Lieberman JR, Ginsberg JS, Paiement G, et al. (October 2003).
2563:
2194:
2096:
1675:
1630:
997:"Secondary prevention of venous thromboembolism with the oral direct thrombin inhibitor ximelagatran"
746:
173:
2641:
1486:
691:
404:
223:
1190:
Lip GY, Rasmussen LH, Olsson SB, Jensen EC, Persson AL, Eriksson U, Wåhlander KF (December 2009).
1777:
1061:
977:
928:
62:
1939:
1342:
1337:
2626:
2301:
2021:
1792:
1782:
1772:
1767:
1762:
1737:
1310:
1297:
1289:
1221:
1172:
1088:
1053:
1018:
969:
920:
879:
804:
757:
726:
592:
announced that it would withdraw pending applications for marketing approval after reports of
88:
52:
761:
317:
1995:
1826:
1787:
1757:
1243:
1211:
1203:
1162:
1045:
1008:
959:
910:
869:
859:
794:
581:
577:
425:
232:
142:
337:
2600:
2431:
2271:
1799:
687:
658:
631:
613:
160:
150:
408:
649:
2241:
2163:
1690:
1376:
1285:
1216:
1191:
874:
847:
593:
1167:
1150:
799:
782:
2610:
2296:
2251:
2231:
2120:
2090:
1680:
1665:
1660:
1621:
1293:
915:
898:
569:
1065:
981:
932:
257:
2540:
2486:
2406:
2316:
2266:
2261:
2110:
2080:
2058:
2053:
2026:
1975:
1804:
1743:
1699:
1576:
1519:
1458:
1453:
1434:
1332:
1301:
750:
738:
654:
109:
104:
2481:
2436:
2426:
2421:
2401:
2396:
2381:
2376:
2361:
2331:
2291:
2246:
2236:
2217:
1980:
1908:
1877:
1809:
1710:
1704:
1694:
1597:
1391:
1381:
635:
589:
1207:
2466:
2451:
2411:
2391:
2371:
2356:
2311:
2306:
2276:
2085:
2002:
1985:
1970:
1949:
1934:
1929:
1872:
1857:
1831:
1821:
1816:
1670:
1639:
1571:
1551:
1529:
1418:
1402:
1398:
1347:
627:
458:
308:
166:
864:
31:
2519:
2446:
2346:
2336:
2321:
2073:
2068:
2048:
2043:
1990:
1944:
1918:
1913:
1862:
1720:
1643:
1607:
1581:
1546:
1534:
1496:
1491:
1481:
1443:
1413:
1408:
1386:
1352:
1327:
995:
Schulman S, Wåhlander K, Lundström T, Clason SB, Eriksson H (October 2003).
722:
186:
1225:
1176:
1092:
1057:
1022:
973:
924:
883:
808:
713:(PTT), respectively. A disadvantage recognised early was the absence of an
39:
17:
2504:
2386:
2366:
2256:
1867:
1852:
1685:
1656:
1647:
1635:
1602:
1448:
1013:
996:
964:
947:
783:"Beyond unfractionated heparin and warfarin: current and future advances"
714:
698:
671:
643:
639:
609:
573:
288:
297:
2138:
2128:
2105:
1903:
1732:
1476:
702:
679:
675:
653:
The conversion of ximelagatran to melagatran. This conversion includes
622:
617:
243:
717:
in case acute bleeding develops, while warfarin can be antagonised by
2524:
2100:
1049:
368:
1134:. AstraZeneca. 21 January 2010. Trial D1250C0004221. Archived from
588:
issues associated with warfarin therapy. In 2006, its manufacturer
357:
1362:
648:
481:
472:
2007:
756:
A chemically different but pharmacologically similar substance,
348:
2190:
1258:
2186:
612:. It is taken orally twice daily, and rapidly absorbed by the
572:
that has been investigated extensively as a replacement for
393:
504:
O=C(NCc1ccc(C(=N\O)\N)cc1)3N(C(=O)(NCC(=O)OCC)C2CCCCC2)CC3
547:
2584:
2533:
2495:
2224:
2119:
2020:
1963:
1890:
1842:
1731:
1719:
1629:
1620:
1590:
1562:
1505:
1467:
1429:
1361:
1318:
1309:
470:
457:
424:
419:
387:
367:
347:
327:
307:
287:
276:
267:
242:
222:
195:
185:
172:
159:
149:
141:
125:
120:
95:
79:
61:
51:
46:
781:Hirsh J, O'Donnell M, Eikelboom JW (July 2007).
256:
828:(Press release). AstraZeneca. February 14, 2006
231:
2202:
1270:
466: g·mol (429 g/mol after conversion)
8:
2287:Budesonide/glycopyrronium bromide/formoterol
30:
2209:
2195:
2187:
1728:
1626:
1315:
1277:
1263:
1255:
407:
316:
1215:
1166:
1012:
963:
914:
873:
863:
848:"Ximelagatran: direct thrombin inhibitor"
798:
336:
826:"AstraZeneca Decides to Withdraw Exanta"
682:in many therapeutic settings, including
2591:
773:
521:
501:
403:
296:
212:ethyl 2-methylcarbamoyl]azetidin-1-yl]-
209:
29:
1149:Eikelboom JW, Weitz JI (April 2010).
903:Journal of Thrombosis and Haemostasis
670:Ximelagatran was expected to replace
376:
7:
2569:
1250:. U.S. National Library of Medicine.
820:
818:
576:that would overcome the problematic
108:
1001:The New England Journal of Medicine
952:The New England Journal of Medicine
852:Vascular Health and Risk Management
356:
247:
705:, which require monitoring of the
25:
2342:Glycopyrronium bromide/formoterol
1168:10.1161/CIRCULATIONAHA.109.853119
800:10.1161/CIRCULATIONAHA.106.685974
686:, prevention of secondary venous
2594:
2568:
2559:
2558:
1892:Direct thrombin (IIa) inhibitors
1320:Glycoprotein IIb/IIIa inhibitors
916:10.1046/j.1538-7836.2003.00034.x
442:
436:
38:
1515:Thromboxane synthase inhibitors
1109:. Astrazenecaclinicaltrials.com
719:prothrombin complex concentrate
529:Key:ZXIBCJHYVWYIKI-PZJWPPBQSA-N
2637:Drugs developed by AstraZeneca
2442:Sodium zirconium cyclosilicate
1132:Clinical Study Report Synopsis
707:international normalized ratio
448:
430:
1:
2515:Cambridge Antibody Technology
1753:Low-molecular-weight heparin
1564:Phosphodiesterase inhibitors
1477:Acetylsalicylic acid/Aspirin
846:Ho SJ, Brighton TA (2006).
741:levels, which prompted the
711:partial thromboplastin time
2658:
2617:Direct thrombin inhibitors
420:Chemical and physical data
2554:
2147:
1725:(with some II inhibition)
749:showed that the elevated
606:direct thrombin inhibitor
537:
512:
492:
214:2-oxo-ethyl]amino]acetate
200:
37:
1208:10.1093/eurheartj/ehp318
865:10.2147/vhrm.2006.2.1.49
2510:Alexion Pharmaceuticals
1248:Drug Information Portal
747:extreme value modelling
2462:Trastuzumab deruxtecan
2457:Tixagevimab/cilgavimab
2352:Isosorbide mononitrate
2035:Plasminogen activators
1507:Thromboxane inhibitors
1431:Prostaglandin analogue
1196:European Heart Journal
1038:Statistics in Medicine
684:deep venous thrombosis
662:
2417:Salbutamol/budesonide
2282:Budesonide/formoterol
2097:serine endopeptidases
1631:Vitamin K antagonists
690:and complications of
652:
134:Withdrawn from market
1844:Direct Xa inhibitors
1676:Ethyl biscoumacetate
1542:Receptor antagonists
1151:"New anticoagulants"
1138:on 10 November 2013.
1014:10.1056/NEJMoa030104
965:10.1056/NEJMoa035162
616:. Ximelagatran is a
1487:Carbasalate calcium
692:atrial fibrillation
34:
2498:acquired companies
2174:Never to phase III
2022:Thrombolytic drugs
1738:glycosaminoglycans
1311:Antiplatelet drugs
1298:antiplatelet drugs
1081:Discovery Medicine
663:
620:, being converted
568:, H 376/95) is an
2582:
2581:
2302:Disufenton sodium
2184:
2183:
2016:
2015:
1886:
1885:
1616:
1615:
1202:(23): 2897–2907.
1161:(13): 1523–1532.
1044:(17): 2914–2923.
1007:(18): 1713–1721.
958:(18): 1703–1712.
727:protamine sulfate
555:
554:
483:Interactive image
389:CompTox Dashboard
16:(Redirected from
2649:
2599:
2598:
2597:
2590:
2572:
2571:
2562:
2561:
2546:Louis Schweitzer
2496:Predecessors and
2211:
2204:
2197:
2188:
1996:Drotrecogin alfa
1976:Antithrombin III
1827:Dermatan sulfate
1800:Oligosaccharides
1729:
1627:
1363:ADP receptor/P2Y
1316:
1279:
1272:
1265:
1256:
1251:
1230:
1229:
1219:
1187:
1181:
1180:
1170:
1146:
1140:
1139:
1124:
1118:
1117:
1115:
1114:
1103:
1097:
1096:
1076:
1070:
1069:
1050:10.1002/sim.6142
1033:
1027:
1026:
1016:
992:
986:
985:
967:
943:
937:
936:
918:
894:
888:
887:
877:
867:
843:
837:
836:
834:
833:
822:
813:
812:
802:
778:
604:Ximelagatran, a
600:Method of action
582:drug interaction
551:
550:
543:
485:
465:
450:
444:
438:
432:
412:
411:
397:
395:
380:
360:
340:
320:
300:
280:
260:
250:
249:
235:
177:
112:
42:
35:
33:
21:
2657:
2656:
2652:
2651:
2650:
2648:
2647:
2646:
2622:Abandoned drugs
2607:
2606:
2605:
2595:
2593:
2585:
2583:
2578:
2550:
2529:
2497:
2491:
2432:Sebelipase alfa
2272:Brompheniramine
2220:
2215:
2185:
2180:
2179:
2164:Clinical trials
2143:
2115:
2025:
2012:
1959:
1882:
1838:
1741:
1736:
1724:
1715:
1691:1,3-Indandiones
1633:
1612:
1586:
1558:
1501:
1463:
1425:
1377:Thienopyridines
1366:
1357:
1305:
1286:Antithrombotics
1283:
1242:
1239:
1234:
1233:
1189:
1188:
1184:
1148:
1147:
1143:
1126:
1125:
1121:
1112:
1110:
1105:
1104:
1100:
1087:(73): 445–450.
1078:
1077:
1073:
1035:
1034:
1030:
994:
993:
989:
945:
944:
940:
896:
895:
891:
845:
844:
840:
831:
829:
824:
823:
816:
780:
779:
775:
770:
735:
725:and heparin by
688:thromboembolism
668:
659:dehydroxylation
634:(replacing the
632:dehydroxylation
614:small intestine
602:
546:
544:
541:(what is this?)
538:
533:
530:
525:
520:
519:
508:
505:
500:
499:
488:
463:
453:
447:
441:
435:
415:
391:
383:
363:
343:
323:
303:
283:
263:
246:
238:
218:
215:
213:
208:
207:
175:
151:Bioavailability
143:Pharmacokinetic
137:
116:
82:
75:
64:
28:
23:
22:
15:
12:
11:
5:
2655:
2653:
2645:
2644:
2639:
2634:
2629:
2624:
2619:
2609:
2608:
2604:
2603:
2580:
2579:
2577:
2576:
2566:
2555:
2552:
2551:
2549:
2548:
2543:
2537:
2535:
2531:
2530:
2528:
2527:
2522:
2517:
2512:
2507:
2501:
2499:
2493:
2492:
2490:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2394:
2389:
2384:
2379:
2374:
2369:
2364:
2359:
2354:
2349:
2344:
2339:
2334:
2329:
2324:
2319:
2314:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2242:Andexanet alfa
2239:
2234:
2228:
2226:
2222:
2221:
2216:
2214:
2213:
2206:
2199:
2191:
2182:
2181:
2178:
2177:
2176:
2175:
2172:
2161:
2155:
2149:
2148:
2145:
2144:
2142:
2141:
2136:
2131:
2125:
2123:
2117:
2116:
2114:
2113:
2108:
2103:
2093:
2088:
2083:
2078:
2077:
2076:
2071:
2063:
2062:
2061:
2056:
2051:
2046:
2031:
2029:
2018:
2017:
2014:
2013:
2011:
2010:
2005:
2000:
1999:
1998:
1988:
1983:
1978:
1973:
1967:
1965:
1961:
1960:
1958:
1957:
1952:
1947:
1942:
1937:
1932:
1923:
1922:
1921:
1916:
1911:
1896:
1894:
1888:
1887:
1884:
1883:
1881:
1880:
1875:
1870:
1865:
1860:
1855:
1849:
1847:
1840:
1839:
1837:
1836:
1835:
1834:
1829:
1824:
1814:
1813:
1812:
1807:
1797:
1796:
1795:
1790:
1785:
1780:
1775:
1770:
1765:
1760:
1749:
1747:
1726:
1717:
1716:
1714:
1713:
1707:
1702:
1697:
1688:
1683:
1678:
1673:
1668:
1663:
1653:
1651:
1624:
1622:Anticoagulants
1618:
1617:
1614:
1613:
1611:
1610:
1605:
1600:
1594:
1592:
1588:
1587:
1585:
1584:
1579:
1574:
1568:
1566:
1560:
1559:
1557:
1556:
1555:
1554:
1549:
1539:
1538:
1537:
1532:
1527:
1511:
1509:
1503:
1502:
1500:
1499:
1494:
1489:
1484:
1479:
1473:
1471:
1469:COX inhibitors
1465:
1464:
1462:
1461:
1456:
1451:
1446:
1440:
1438:
1427:
1426:
1424:
1423:
1422:
1421:
1416:
1411:
1396:
1395:
1394:
1389:
1384:
1373:
1371:
1364:
1359:
1358:
1356:
1355:
1350:
1345:
1340:
1335:
1330:
1324:
1322:
1313:
1307:
1306:
1294:anticoagulants
1284:
1282:
1281:
1274:
1267:
1259:
1253:
1252:
1244:"Ximelagatran"
1238:
1237:External links
1235:
1232:
1231:
1182:
1141:
1119:
1098:
1071:
1028:
987:
938:
889:
838:
814:
793:(5): 552–560.
772:
771:
769:
766:
734:
731:
709:(INR) and the
674:and sometimes
667:
664:
601:
598:
594:hepatotoxicity
553:
552:
535:
534:
532:
531:
528:
526:
523:
515:
514:
513:
510:
509:
507:
506:
503:
495:
494:
493:
490:
489:
487:
486:
478:
476:
468:
467:
461:
455:
454:
451:
445:
439:
433:
428:
422:
421:
417:
416:
414:
413:
400:
398:
385:
384:
382:
381:
373:
371:
365:
364:
362:
361:
353:
351:
345:
344:
342:
341:
333:
331:
325:
324:
322:
321:
313:
311:
305:
304:
302:
301:
293:
291:
285:
284:
282:
281:
273:
271:
265:
264:
262:
261:
253:
251:
240:
239:
237:
236:
228:
226:
220:
219:
217:
216:
211:
203:
202:
201:
198:
197:
193:
192:
189:
183:
182:
179:
170:
169:
163:
157:
156:
153:
147:
146:
139:
138:
136:
135:
131:
129:
123:
122:
118:
117:
115:
114:
101:
99:
93:
92:
85:
83:administration
77:
76:
74:
73:
69:
67:
59:
58:
55:
49:
48:
44:
43:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2654:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2614:
2612:
2602:
2592:
2588:
2575:
2567:
2565:
2557:
2556:
2553:
2547:
2544:
2542:
2539:
2538:
2536:
2532:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2506:
2503:
2502:
2500:
2494:
2488:
2485:
2483:
2480:
2478:
2475:
2473:
2470:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2373:
2370:
2368:
2365:
2363:
2360:
2358:
2355:
2353:
2350:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2303:
2300:
2298:
2297:Dapagliflozin
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2252:Asfotase alfa
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2232:Acalabrutinib
2230:
2229:
2227:
2223:
2219:
2212:
2207:
2205:
2200:
2198:
2193:
2192:
2189:
2173:
2171:
2168:
2167:
2165:
2162:
2159:
2156:
2154:
2151:
2150:
2146:
2140:
2137:
2135:
2132:
2130:
2127:
2126:
2124:
2122:
2121:Non-medicinal
2118:
2112:
2109:
2107:
2104:
2102:
2098:
2094:
2092:
2091:Streptokinase
2089:
2087:
2084:
2082:
2079:
2075:
2072:
2070:
2067:
2066:
2064:
2060:
2057:
2055:
2052:
2050:
2047:
2045:
2042:
2041:
2040:
2036:
2033:
2032:
2030:
2028:
2027:fibrinolytics
2023:
2019:
2009:
2006:
2004:
2001:
1997:
1994:
1993:
1992:
1989:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1968:
1966:
1962:
1956:
1953:
1951:
1948:
1946:
1943:
1941:
1938:
1936:
1933:
1931:
1927:
1924:
1920:
1917:
1915:
1912:
1910:
1907:
1906:
1905:
1901:
1898:
1897:
1895:
1893:
1889:
1879:
1876:
1874:
1871:
1869:
1866:
1864:
1861:
1859:
1856:
1854:
1851:
1850:
1848:
1845:
1841:
1833:
1830:
1828:
1825:
1823:
1820:
1819:
1818:
1815:
1811:
1808:
1806:
1803:
1802:
1801:
1798:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1764:
1761:
1759:
1756:
1755:
1754:
1751:
1750:
1748:
1745:
1739:
1734:
1730:
1727:
1722:
1718:
1712:
1708:
1706:
1703:
1701:
1698:
1696:
1692:
1689:
1687:
1684:
1682:
1681:Phenprocoumon
1679:
1677:
1674:
1672:
1669:
1667:
1666:Coumatetralyl
1664:
1662:
1661:Acenocoumarol
1658:
1655:
1654:
1652:
1649:
1645:
1641:
1637:
1632:
1628:
1625:
1623:
1619:
1609:
1606:
1604:
1601:
1599:
1596:
1595:
1593:
1589:
1583:
1580:
1578:
1575:
1573:
1570:
1569:
1567:
1565:
1561:
1553:
1550:
1548:
1545:
1544:
1543:
1540:
1536:
1533:
1531:
1528:
1525:
1521:
1518:
1517:
1516:
1513:
1512:
1510:
1508:
1504:
1498:
1495:
1493:
1490:
1488:
1485:
1483:
1480:
1478:
1475:
1474:
1472:
1470:
1466:
1460:
1457:
1455:
1452:
1450:
1447:
1445:
1442:
1441:
1439:
1436:
1432:
1428:
1420:
1417:
1415:
1412:
1410:
1407:
1406:
1404:
1400:
1397:
1393:
1390:
1388:
1385:
1383:
1380:
1379:
1378:
1375:
1374:
1372:
1370:
1367:
1360:
1354:
1351:
1349:
1346:
1344:
1341:
1339:
1336:
1334:
1331:
1329:
1326:
1325:
1323:
1321:
1317:
1314:
1312:
1308:
1303:
1299:
1295:
1291:
1290:thrombolytics
1287:
1280:
1275:
1273:
1268:
1266:
1261:
1260:
1257:
1249:
1245:
1241:
1240:
1236:
1227:
1223:
1218:
1213:
1209:
1205:
1201:
1197:
1193:
1186:
1183:
1178:
1174:
1169:
1164:
1160:
1156:
1152:
1145:
1142:
1137:
1133:
1129:
1123:
1120:
1108:
1102:
1099:
1094:
1090:
1086:
1082:
1075:
1072:
1067:
1063:
1059:
1055:
1051:
1047:
1043:
1039:
1032:
1029:
1024:
1020:
1015:
1010:
1006:
1002:
998:
991:
988:
983:
979:
975:
971:
966:
961:
957:
953:
949:
942:
939:
934:
930:
926:
922:
917:
912:
908:
904:
900:
893:
890:
885:
881:
876:
871:
866:
861:
857:
853:
849:
842:
839:
827:
821:
819:
815:
810:
806:
801:
796:
792:
788:
784:
777:
774:
767:
765:
763:
759:
754:
752:
748:
744:
740:
732:
730:
728:
724:
720:
716:
712:
708:
704:
700:
695:
693:
689:
685:
681:
677:
673:
665:
660:
656:
651:
647:
645:
641:
637:
633:
629:
625:
624:
619:
615:
611:
607:
599:
597:
595:
591:
587:
583:
579:
575:
571:
570:anticoagulant
567:
563:
559:
549:
542:
536:
527:
522:
518:
511:
502:
498:
491:
484:
480:
479:
477:
474:
469:
462:
460:
456:
429:
427:
423:
418:
410:
406:
405:DTXSID5049075
402:
401:
399:
390:
386:
379:
375:
374:
372:
370:
366:
359:
355:
354:
352:
350:
346:
339:
335:
334:
332:
330:
326:
319:
315:
314:
312:
310:
306:
299:
295:
294:
292:
290:
286:
279:
275:
274:
272:
270:
266:
259:
255:
254:
252:
245:
241:
234:
230:
229:
227:
225:
221:
210:
206:
199:
194:
190:
188:
184:
180:
178:
171:
168:
164:
162:
158:
154:
152:
148:
144:
140:
133:
132:
130:
128:
124:
119:
111:
106:
103:
102:
100:
98:
94:
90:
86:
84:
78:
72:Uncategorized
71:
70:
68:
66:
60:
56:
54:
50:
47:Clinical data
45:
41:
36:
27:Anticoagulant
19:
2632:Hepatotoxins
2541:Tom McKillop
2487:Zolmitriptan
2477:Ximelagatran
2476:
2407:Rosuvastatin
2317:Esomeprazole
2267:Bicalutamide
2262:Benralizumab
2111:Fibrinolysin
2081:Anistreplase
2059:Desmoteplase
2054:Tenecteplase
1955:Ximelagatran
1954:
1805:Fondaparinux
1744:antithrombin
1700:Diphenadione
1577:Dipyridamole
1520:Dipyridamole
1459:Treprostinil
1454:Prostacyclin
1333:Eptifibatide
1247:
1199:
1195:
1185:
1158:
1154:
1144:
1136:the original
1131:
1122:
1111:. Retrieved
1101:
1084:
1080:
1074:
1041:
1037:
1031:
1004:
1000:
990:
955:
951:
941:
909:(1): 41–47.
906:
902:
892:
858:(1): 49–58.
855:
851:
841:
830:. Retrieved
790:
786:
776:
755:
751:liver enzyme
739:liver enzyme
736:
733:Side effects
696:
669:
655:dealkylation
642:groups with
621:
603:
565:
561:
558:Ximelagatran
557:
556:
545:
539:
378:ChEMBL522038
174:Elimination
127:Legal status
121:Legal status
32:Ximelagatran
2482:Zafirlukast
2437:Selumetinib
2427:Saxagliptin
2422:Savolitinib
2402:Roflumilast
2397:Ravulizumab
2382:Palivizumab
2377:Osimertinib
2362:Motavizumab
2332:Fulvestrant
2292:Candesartan
2247:Anifrolumab
2237:Anastrozole
2218:AstraZeneca
2160:from market
1981:Defibrotide
1909:Bivalirudin
1878:Rivaroxaban
1817:Heparinoids
1810:Idraparinux
1711:Tioclomarol
1705:Phenindione
1695:Clorindione
1598:Cloricromen
1392:Ticlopidine
1382:Clopidogrel
1155:Circulation
787:Circulation
590:AstraZeneca
233:192939-46-1
196:Identifiers
191:Renal (80%)
53:Trade names
2642:Azetidines
2611:Categories
2467:Vandetanib
2452:Ticagrelor
2412:Roxadustat
2392:Quetiapine
2372:Omeprazole
2357:Metoprolol
2312:Eculizumab
2307:Durvalumab
2277:Budesonide
2086:Monteplase
2003:Ramatroban
1986:Nafamostat
1971:Abelacimab
1950:Melagatran
1935:Dabigatran
1930:Argatroban
1873:Otamixaban
1858:Betrixaban
1846:("xabans")
1832:Sulodexide
1822:Danaparoid
1793:Tinzaparin
1783:Parnaparin
1778:Nadroparin
1773:Enoxaparin
1768:Dalteparin
1763:Certoparin
1723:inhibitors
1671:Dicoumarol
1572:Cilostazol
1552:Terutroban
1530:Picotamide
1419:Ticagrelor
1403:nucleoside
1399:Nucleotide
1369:inhibitors
1348:Sibrafiban
1113:2012-10-16
832:2012-07-16
768:References
628:hydrolysis
586:monitoring
471:3D model (
459:Molar mass
338:49HFB70472
309:ChemSpider
269:IUPHAR/BPS
224:CAS Number
205:IUPAC name
167:melagatran
161:Metabolism
18:Melagatran
2520:MedImmune
2472:Vaxzevria
2447:Tamoxifen
2347:Goserelin
2337:Gefitinib
2322:Exenatide
2170:Phase III
2158:Withdrawn
2074:Urokinase
2069:Saruplase
2049:Reteplase
2044:Alteplase
1991:Protein C
1945:Inogatran
1940:Efegatran
1926:Univalent
1919:Lepirudin
1914:Desirudin
1863:Darexaban
1788:Reviparin
1758:Bemiparin
1721:Factor Xa
1657:Coumarins
1634:(inhibit
1608:Vorapaxar
1582:Triflusal
1547:Terbogrel
1535:Terbogrel
1524:+ aspirin
1497:Triflusal
1492:Indobufen
1482:Aloxiprin
1444:Beraprost
1414:Elinogrel
1409:Cangrelor
1387:Prasugrel
1353:Tirofiban
1343:Roxifiban
1338:Orbofiban
1328:Abciximab
1107:"AZD0837"
723:vitamin K
187:Excretion
181:3–5 hours
176:half-life
81:Routes of
63:Pregnancy
2627:Prodrugs
2601:Medicine
2564:Category
2505:Astra AB
2387:Propofol
2367:Olaparib
2257:Atenolol
2225:Products
1900:Bivalent
1868:Edoxaban
1853:Apixaban
1686:Warfarin
1603:Ditazole
1449:Iloprost
1405:analogs
1226:19690349
1177:20368532
1093:22742650
1066:36324117
1058:24623062
1023:14585939
982:26026547
974:14585938
933:20556829
925:12871538
884:17319469
809:17664384
758:AZD-0837
715:antidote
699:warfarin
672:warfarin
644:hydrogen
640:hydroxyl
610:thrombin
574:warfarin
548:(verify)
289:DrugBank
97:ATC code
65:category
2574:Commons
2327:FluMist
2139:Oxalate
2129:Citrate
2106:Brinase
1904:Hirudin
1733:Heparin
1709:Other:
1217:2785945
875:1993972
762:ARH0637
721:and/or
703:heparin
680:heparin
676:aspirin
623:in vivo
618:prodrug
578:dietary
464:473.574
426:Formula
318:7848559
298:DB04898
258:9574101
244:PubChem
113:)
107: (
105:B01AE05
89:tablets
2587:Portal
2534:People
2525:Zeneca
2153:WHO-EM
2101:Ancrod
2095:Other
1742:(bind
1735:group/
1224:
1214:
1175:
1091:
1064:
1056:
1021:
980:
972:
931:
923:
882:
872:
807:
584:, and
566:Exarta
562:Exanta
497:SMILES
369:ChEMBL
358:D01981
87:Oral (
57:Exanta
2039:r-tPA
1964:Other
1591:Other
1062:S2CID
978:S2CID
929:S2CID
636:ethyl
517:InChI
473:JSmol
2134:EDTA
2065:UPA
2008:REG1
1435:PGI2
1296:and
1222:PMID
1173:PMID
1089:PMID
1054:PMID
1019:PMID
970:PMID
921:PMID
880:PMID
805:PMID
701:and
678:and
666:Uses
657:and
638:and
630:and
349:KEGG
329:UNII
278:6381
145:data
1640:VII
1302:B01
1300:) (
1212:PMC
1204:doi
1163:doi
1159:121
1046:doi
1009:doi
1005:349
960:doi
956:349
911:doi
870:PMC
860:doi
795:doi
791:116
743:FDA
646:).
564:or
394:EPA
248:CID
165:to
155:20%
110:WHO
2613::
2166::
2099::
2037::
1928::
1902::
1693::
1659::
1646:,
1644:IX
1642:,
1638:,
1636:II
1365:12
1292:,
1246:.
1220:.
1210:.
1200:30
1198:.
1194:.
1171:.
1157:.
1153:.
1130:.
1085:13
1083:.
1060:.
1052:.
1042:33
1040:.
1017:.
1003:.
999:.
976:.
968:.
954:.
950:.
927:.
919:.
905:.
901:.
878:.
868:.
854:.
850:.
817:^
803:.
789:.
785:.
729:.
580:,
440:35
434:24
2589::
2210:e
2203:t
2196:v
2024:/
1746:)
1740:/
1650:)
1648:X
1526:)
1522:(
1437:)
1433:(
1401:/
1304:)
1288:(
1278:e
1271:t
1264:v
1228:.
1206::
1179:.
1165::
1116:.
1095:.
1068:.
1048::
1025:.
1011::
984:.
962::
935:.
913::
907:1
886:.
862::
856:2
835:.
811:.
797::
661:.
560:(
475:)
452:5
449:O
446:5
443:N
437:H
431:C
396:)
392:(
91:)
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
