551:
InChI=1S/C230H320N63O125P19S19/c1-98-55-274(217(308)254-178(98)231)142-45-112(400-419(322,438)361-70-124-113(46-143(381-124)275-56-99(2)179(232)255-218(275)309)401-423(326,442)367-76-130-119(52-149(387-130)288-92-248-152-183(236)242-89-245-186(152)288)407-427(330,446)369-78-132-121(54-151(389-132)290-94-252-156-190(290)260-215(240)263-202(156)306)408-425(328,444)365-72-125-114(47-144(382-125)276-57-100(3)180(233)256-219(276)310)406-428(331,447)372-81-134-160(171(354-38-28-344-18)206(393-134)283-64-107(10)196(300)269-226(283)317)412-432(335,451)375-84-137-163(173(356-40-30-346-20)208(395-137)285-66-109(12)198(302)271-228(285)319)415-435(338,454)377-86-139-165(175(358-42-32-348-22)210(397-139)287-68-111(14)200(304)273-230(287)321)416-436(339,455)379-87-140-166(176(359-43-33-349-23)212(398-140)292-96-250-154-185(238)244-91-247-188(154)292)417-430(333,449)371-80-133-158(295)168(351-35-25-341-15)204(391-133)282-63-106(9)195(299)268-225(282)316)123(380-142)71-362-421(324,440)403-117-50-147(279-61-104(7)193(297)266-223(279)314)386-128(117)75-366-426(329,445)409-120-53-150(289-93-251-155-189(289)259-214(239)262-201(155)305)388-131(120)77-368-424(327,443)405-118-51-148(280-62-105(8)194(298)267-224(280)315)385-127(118)74-364-422(325,441)404-116-49-146(278-60-103(6)192(296)265-222(278)313)384-126(116)73-363-420(323,439)402-115-48-145(277-58-101(4)181(234)257-220(277)311)383-129(115)79-370-429(332,448)411-162-136(394-207(172(162)355-39-29-345-19)284-65-108(11)197(301)270-227(284)318)83-374-434(337,453)414-164-138(396-209(174(164)357-41-31-347-21)286-67-110(13)199(303)272-229(286)320)85-376-433(336,452)413-161-135(392-205(170(161)353-37-27-343-17)281-59-102(5)182(235)258-221(281)312)82-378-437(340,456)418-167-141(399-213(177(167)360-44-34-350-24)293-97-253-157-191(293)261-216(241)264-203(157)307)88-373-431(334,450)410-159-122(69-294)390-211(169(159)352-36-26-342-16)291-95-249-153-184(237)243-90-246-187(153)291/h55-68,89-97,112-151,158-177,204-213,294-295H,25-54,69-88H2,1-24H3,(H,322,438)(H,323,439)(H,324,440)(H,325,441)(H,326,442)(H,327,443)(H,328,444)(H,329,445)(H,330,446)(H,331,447)(H,332,448)(H,333,449)(H,334,450)(H,335,451)(H,336,452)(H,337,453)(H,338,454)(H,339,455)(H,340,456)(H2,231,254,308)(H2,232,255,309)(H2,233,256,310)(H2,234,257,311)(H2,235,258,312)(H2,236,242,245)(H2,237,243,246)(H2,238,244,247)(H,265,296,313)(H,266,297,314)(H,267,298,315)(H,268,299,316)(H,269,300,317)(H,270,301,318)(H,271,302,319)(H,272,303,320)(H,273,304,321)(H3,239,259,262,305)(H3,240,260,263,306)(H3,241,261,264,307)/t112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122+,123+,124+,125+,126+,127+,128+,129+,130+,131+,132+,133+,134+,135+,136+,137+,138+,139+,140+,141+,142+,143+,144+,145+,146+,147+,148+,149+,150+,151+,158+,159+,160+,161+,162+,163+,164+,165+,166+,167+,168+,169+,170+,171+,172+,173+,174+,175+,176+,177+,204+,205+,206+,207+,208+,209+,210+,211+,212+,213+,419?,420?,421?,422?,423?,424?,425?,426?,427?,428?,429?,430?,431?,432?,433?,434?,435?,436?,437?/m0/s1
531:
Cc1cn(c(=O)c1=O)2C((O2)COP(=O)(O3C(O3COP(=O)(O4C(O4COP(=O)(O5(O(5OCCOC)n6cc(c(=O)c6=O)C)COP(=O)(O7(O(7OCCOC)n8cc(c(=O)c8=O)C)COP(=O)(O9(O(9OCCOC)n1cc(c(nc1=O)N)C)COP(=O)(O1(O(1OCCOC)n1cnc2c1nc(c2=O)N)COP(=O)(O1(O(1OCCOC)n1cnc2c1ncnc2N)CO)S)S)S)S)S)n1cc(c(nc1=O)N)C)S)n1cc(c(=O)c1=O)C)S)OP(=O)(OC1(C(O1)n1cnc2c1nc(c2=O)N)OP(=O)(OC1(C(O1)n1cc(c(=O)c1=O)C)OP(=O)(OC1(C(O1)n1cc(c(nc1=O)N)C)OP(=O)(OC1(C(O1)n1cc(c(nc1=O)N)C)OP(=O)(OC1(C(O1)n1cnc2c1ncnc2N)OP(=O)(OC1(C(O1)n1cnc2c1nc(c2=O)N)OP(=O)(OC1(C(O1)n1cc(c(nc1=O)N)C)OP(=O)(OC1(((O1)n1cc(c(=O)c1=O)C)OCCOC)OP(=O)(OC1(((O1)n1cc(c(=O)c1=O)C)OCCOC)OP(=O)(OC1(((O1)n1cc(c(=O)c1=O)C)OCCOC)OP(=O)(OC1(((O1)n1cnc2c1ncnc2N)OCCOC)OP(=O)(OC1(((O1)n1cc(c(=O)c1=O)C)OCCOC)O)S)S)S)S)S)S)S)S)S)S)S)S
29:
785:
1924:
614:
Familial chylomicronaemia syndrome (FCS) (also known as type I hyperlipoproteinaemia) is an inherited disease where people have abnormally high levels of some types of fat called triglycerides in their blood. The excess fat accumulates in organs such as the spleen and liver, which become abnormally
605:
Volanesorsen, is an 'antisense oligonucleotide,' a very short piece of synthetic RNA (a type of genetic material). It has been designed to block the production of a protein that slows down the breakdown of fats called apolipoprotein C-III. By blocking the production of this protein, the medicine
663:
Volanesorsen was effective in reducing triglycerides in the blood in a study of 67 participants with familial chylomicronemia syndrome (FCS). After three months, participants given volanesorsen had an average 77% reduction in the level of triglycerides compared with an average 18% increase in
618:
Volanesorsen is indicated as an adjunct to diet in adults with genetically confirmed familial chylomicronemia syndrome (FCS) and at high risk for pancreatitis, in whom response to diet and triglyceride lowering therapy has been inadequate.
615:
enlarged. Fat accumulation can also cause repeated bouts of pancreatitis (inflammation of the pancreas) and xanthomas (formation of yellow fatty deposits just under the skin, generally around joints)
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participants given placebo (a dummy treatment). All participants in the study were on a low-fat diet in addition to receiving volanesorsen or placebo.
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reduces the level of triglycerides in the blood and, as a result, fat accumulation in the body, which is expected to reduce the risk of pancreatitis.
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The most common side effects include reduced platelet levels and reactions at the site of the injection such as pain, swelling, itching, or bruising.
1157:
657:(EMA) in February 2014, for phosphorothioate oligonucleotide targeted to apolipoprotein C-III for treatment of familial chylomicronaemia syndrome.
1110:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1013:
Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
1051:"Antisense-Mediated Lowering of Plasma Apolipoprotein C-III by Volanesorsen Improves Dyslipidemia and Insulin Sensitivity in Type 2 Diabetes"
523:
851:
World Health
Organization (2016). "International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 75".
1824:
931:"Antisense oligonucleotide inhibition of apolipoprotein C-III reduces plasma triglycerides in rodents, nonhuman primates, and humans"
1409:
882:"Very-Low-Density Lipoprotein-Associated Apolipoproteins Predict Cardiovascular Events and Are Lowered by Inhibition of APOC-III"
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1024:
819:"Waylivra (volanesorsen) 285 mg solution for injection in pre-filled syringe - Summary of Product Characteristics (SmPC)"
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Digenio A, Dunbar RL, Alexander VJ, Hompesch M, Morrow L, Lee RG, et al. (August 2016).
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Pechlaner R, Tsimikas S, Yin X, Willeit P, Baig F, Santer P, et al. (February 2017).
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Graham MJ, Lee RG, Bell TA, Fu W, Mullick AE, Alexander VJ, et al. (May 2013).
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Volanesorsen was approved for medical use in the
European Union in May 2019.
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It is in Phase III clinical trials for the treatment of
1025:"Ionis' volanesorsen hits efficacy endpoint in phase 3"
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1936:
988:
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301:
1151:
886:Journal of the American College of Cardiology
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133:In general: ℞ (Prescription only)
1158:
1144:
672:The complete sequence of volanesorsen is:
374:
228:-thiothymidylyl-(3'→5')-2'-deoxy-5-methyl-
1825:Magnesium pyridoxal 5-phosphate glutamate
1066:
946:
905:
864:
642:The drug was discovered and developed by
394:
232:-thiocytidylyl-(3'→5')-2'-deoxy-5-methyl-
873:
783:
244:-thioguanylyl-(3'→5')-2'-deoxy-5-methyl-
208:-thiouridylyl-(3'→5')-2'-deoxy-5-methyl-
354:
1937:
1022:
125:
112:
1139:
922:
846:
844:
842:
840:
441:
1131:. U.S. National Library of Medicine.
85:
421:
414:
325:
13:
837:
487:
220:- thiothymidylyl-(3'→5')-2'-deoxy-
14:
1971:
1189:Cholesterol absorption inhibitors
1117:
799:International nonproprietary name
633:familial chylomicronemia syndrome
284:-(2-methoxyethyl)-5-methyluridine
1922:
581:-methoxyethyl (2'-MOE) chimeric
475:
469:
236:-thiocytidylyl-(3'→5')-2'-deoxy-
27:
649:Volanesorsen was designated an
609:
577:. It is a second-generation 2'-
556:Key:IJUQCWMZCMFFJP-GQSLRNSLSA-N
240:-thioadenylyl-(3'→5')-2'-deoxy-
1083:
1042:
1023:Taylor NP (20 December 2016).
1016:
811:
637:familial partial lipodystrophy
493:
481:
463:
1:
948:10.1161/CIRCRESAHA.111.300367
804:
667:
569:, sold under the brand name
204:-(2- methoxyethyl)-5-methyl-
7:
1955:Therapeutic gene modulation
268:-(2-methoxyethyl)-5-methyl-
260:-(2-methoxyethyl)-5-methyl-
252:-(2-methoxyethyl)-5-methyl-
196:-(2-methoxyethyl)-5-methyl-
188:-(2-methoxyethyl)-5-methyl-
54:ISIS 304801, ISIS-APOCIIIRx
10:
1976:
898:10.1016/j.jacc.2016.11.065
622:
575:triglyceride-reducing drug
453:Chemical and physical data
248:-thiocytidylyl-(3'→5')-2'-
192:-thiocytidylyl-(3'→5')-2'-
1873:
1840:Omega−3-acid ethyl esters
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1096:European Medicines Agency
999:European Medicines Agency
655:European Medicines Agency
539:
519:
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405:
385:
365:
345:
320:
292:
280:-thioadenylyl-(3'→5')-2'-
272:-thiouridylyl-(3'→5')-2'-
264:-thiouridylyl-(3'→5')-2'-
256:-thiouridylyl-(3'→5')-2'-
200:-thiouridylyl-(3'→5')-2'-
184:-thioguanylyl-(3'→5')-2'-
176:-thioadenylyl-(3'→5')-2'-
145:
140:
102:
97:
72:
58:
50:
40:
35:
26:
1739:Bempedoic acid/ezetimibe
1360:Niacin and derivatives (
792:
216:-thiothymidylyl-(3'→5')-
1764:Fenofibrate/simvastatin
1759:Fenofibrate/pravastatin
1734:Amlodipine/atorvastatin
1129:Drug Information Portal
588:(ASO) that targets the
212:-thiocytidylyl-(3'→5')-
1749:Ezetimibe/rosuvastatin
1744:Ezetimibe/atorvastatin
1221:Bile acid sequestrants
789:
224:-thioguanylyl-(3'→5')-
1754:Ezetimibe/simvastatin
1167:Lipid-lowering agents
1029:www.fiercebiotech.com
787:
644:Ionis Pharmaceuticals
583:antisense therapeutic
1950:Hypolipidemic agents
1795:Alipogene tiparvovec
1521:Aluminium clofibrate
1380:Aluminium nicotinate
935:Circulation Research
853:WHO Drug Information
797:Volanesorsen is the
1531:Choline fenofibrate
1100:. 17 September 2018
1003:. 24 September 2018
121:(Prescription only)
23:
1900:Never to phase III
1779:Niacin/simvastatin
1769:Niacin/laropiprant
790:
788:Chemical structure
629:hypertriglycidemia
276:-(2-methoxyethyl)-
180:-(2-methoxyethyl)-
172:-(2-Methoxyethyl)-
19:
1910:
1909:
1774:Niacin/lovastatin
1722:
1721:
1610:
1609:
1488:
1487:
1443:ATP citrate lyase
1400:Nicotinyl alcohol
1298:HMG-CoA reductase
1279:
1278:
1068:10.2337/dc16-0126
766:-(2-methoxyethyl)
564:
563:
129:
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16:Chemical compound
1967:
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1659:PCSK9 inhibitors
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825:. 28 August 2019
815:
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594:apolipoprotein C
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1890:Clinical trials
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1616:CETP inhibitors
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1475:Dextrothyroxine
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1021:
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1004:
994:"Waylivra EPAR"
992:
991:
964:
941:(11): 1479–90.
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586:oligonucleotide
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1456:Bempedoic acid
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1133:
1125:"Volanesorsen"
1119:
1118:External links
1116:
1113:
1112:
1091:"EU/3/14/1249"
1082:
1061:(8): 1408–15.
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892:(7): 789–800.
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402:
400:
399:
391:
389:
383:
382:
380:
379:
371:
369:
363:
362:
360:
359:
351:
349:
343:
342:
340:
339:
331:
329:
318:
317:
315:
314:
298:
296:
290:
289:
287:
286:
156:
148:
147:
146:
143:
142:
138:
137:
135:
134:
131:
122:
108:
106:
100:
99:
95:
94:
92:
91:
78:
76:
70:
69:
64:
62:administration
56:
55:
52:
48:
47:
44:
38:
37:
33:
32:
15:
9:
6:
4:
3:
2:
1972:
1961:
1958:
1956:
1953:
1951:
1948:
1946:
1945:Antisense RNA
1943:
1942:
1940:
1930:
1920:
1919:
1916:
1899:
1897:
1894:
1893:
1891:
1888:
1885:
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1880:
1877:
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1866:
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1826:
1823:
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1803:
1801:
1798:
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1765:
1762:
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1737:
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1732:
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1725:
1715:
1712:
1711:
1709:
1706:
1702:
1698:
1694:
1688:
1685:
1683:
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1678:
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1673:
1670:
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1664:
1660:
1656:
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1632:
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1627:
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1613:
1603:
1600:
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1587:
1584:
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1579:
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1569:
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1564:
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1559:
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1537:
1534:
1532:
1529:
1527:
1524:
1522:
1519:
1518:
1516:
1514:
1510:
1507:
1504:
1503:PPAR agonists
1500:
1497:
1495:
1494:Blood vessels
1491:
1481:
1478:
1476:
1473:
1472:
1470:
1467:
1466:Thyromimetics
1463:
1457:
1454:
1453:
1451:
1448:
1444:
1440:
1434:
1431:
1429:
1426:
1424:
1421:
1420:
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1411:
1407:
1401:
1398:
1396:
1393:
1391:
1388:
1386:
1383:
1381:
1378:
1376:
1373:
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1367:
1363:
1358:
1352:
1349:
1347:
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1342:
1339:
1337:
1334:
1332:
1329:
1327:
1324:
1322:
1319:
1317:
1314:
1312:
1309:
1308:
1306:
1303:
1299:
1295:
1291:
1288:
1286:
1282:
1272:
1268:
1264:
1263:Soluble fiber
1261:
1259:
1256:
1254:
1253:Colestyramine
1251:
1249:
1246:
1244:
1241:
1239:
1236:
1235:
1233:
1230:
1226:
1222:
1218:
1212:
1209:
1207:
1204:
1202:
1199:
1198:
1196:
1194:
1190:
1186:
1183:
1181:
1177:
1172:
1168:
1161:
1156:
1154:
1149:
1147:
1142:
1141:
1138:
1130:
1126:
1122:
1121:
1099:
1097:
1092:
1086:
1078:
1074:
1069:
1064:
1060:
1056:
1055:Diabetes Care
1052:
1045:
1030:
1026:
1019:
1002:
1000:
995:
989:
987:
985:
983:
981:
979:
977:
975:
973:
971:
969:
967:
958:
954:
949:
944:
940:
936:
932:
925:
917:
913:
908:
903:
899:
895:
891:
887:
883:
876:
867:
862:
858:
854:
847:
845:
843:
841:
824:
820:
814:
810:
802:
800:
786:
776:
770:
769:
765:
758:
757:
752:
748:
744:
740:
736:
732:
728:
724:
720:
716:
712:
708:
704:
700:
696:
692:
688:
684:
680:
675:
674:
673:
665:
661:
658:
656:
652:
647:
645:
640:
638:
634:
630:
620:
616:
607:
603:
600:
598:
591:
590:messenger RNA
587:
584:
580:
576:
572:
568:
554:
549:
548:
545:
538:
529:
528:
525:
518:
507:
505:
501:
462:
460:
456:
451:
444:
443:ChEMBL3544994
440:
439:
437:
435:
431:
424:
420:
417:
413:
412:
410:
408:
404:
397:
393:
392:
390:
388:
384:
377:
373:
372:
370:
368:
364:
357:
353:
352:
350:
348:
344:
337:
333:
332:
330:
323:
319:
312:
308:
304:
300:
299:
297:
295:
291:
283:
279:
275:
271:
267:
263:
259:
255:
251:
247:
243:
239:
235:
231:
227:
223:
219:
215:
211:
207:
203:
199:
195:
191:
187:
183:
179:
175:
171:
167:
163:
159:
155:
154:
151:
144:
139:
132:
130: Rx-only
123:
120:
110:
109:
107:
105:
101:
96:
88:
83:
80:
79:
77:
75:
71:
68:
65:
63:
57:
53:
49:
45:
43:
39:
36:Clinical data
34:
30:
25:
1960:Orphan drugs
1865:Volanesorsen
1864:
1727:Combinations
1699:inhibitors (
1541:Clinofibrate
1536:Ciprofibrate
1445:inhibitors (
1412:inhibitors (
1395:Nicofuranose
1346:Rosuvastatin
1336:Pitavastatin
1316:Cerivastatin
1311:Atorvastatin
1128:
1102:. Retrieved
1094:
1085:
1058:
1054:
1044:
1032:. Retrieved
1028:
1018:
1005:. Retrieved
997:
938:
934:
924:
889:
885:
875:
866:10665/331046
859:(1): 165–6.
856:
852:
827:. Retrieved
822:
813:
796:
763:
671:
662:
659:
648:
641:
626:
617:
613:
610:Medical uses
604:
601:
599:(apo-CIII).
578:
570:
567:Volanesorsen
566:
565:
307:1573402-50-2
281:
277:
273:
269:
265:
261:
257:
253:
249:
245:
241:
237:
233:
229:
225:
221:
217:
213:
209:
205:
201:
197:
193:
189:
185:
181:
177:
173:
169:
165:
161:
157:
104:Legal status
98:Legal status
67:Subcutaneous
21:Volanesorsen
1886:from market
1845:Policosanol
1820:Lapaquistat
1800:Azacosterol
1677:Bococizumab
1649:Torcetrapib
1644:Obicetrapib
1639:Evacetrapib
1634:Dalcetrapib
1629:Anacetrapib
1581:Ronifibrate
1576:Pemafibrate
1566:Gemfibrozil
1561:Fenofibrate
1526:Bezafibrate
1433:Mitratapide
1423:Dirlotapide
1351:Simvastatin
1341:Pravastatin
1321:Fluvastatin
1271:glucomannan
1238:Colesevelam
1034:22 December
651:orphan drug
515: g·mol
303:915430-78-3
141:Identifiers
51:Other names
42:Trade names
1939:Categories
1860:Triparanol
1835:Mipomersen
1815:Darapladib
1810:Benfluorex
1805:Azalanstat
1714:Evinacumab
1687:Inclisiran
1682:Evolocumab
1672:Alirocumab
1586:Simfibrate
1556:Etofibrate
1551:Clofibride
1546:Clofibrate
1480:Resmetirom
1428:Lomitapide
1390:Niceritrol
1331:Mevastatin
1326:Lovastatin
1248:Colestipol
1243:Colestilan
1206:Hyzetimibe
805:References
780:= 2'-deoxy
774:= 5-methyl
504:Molar mass
396:2O4BE0K238
367:ChemSpider
294:CAS Number
150:IUPAC name
1896:Phase III
1884:Withdrawn
1571:Nafenopin
1258:Colextran
1211:SCH-48461
1201:Ezetimibe
668:Chemistry
336:122409770
60:Routes of
1929:Medicine
1855:Tiadenol
1850:Probucol
1830:Meglutol
1602:GW501516
1513:Fibrates
1375:Acipimox
1267:psyllium
1265:such as
1180:GI tract
1077:27271183
957:23542898
916:28209220
571:Waylivra
376:34982934
347:DrugBank
74:ATC code
46:Waylivra
1697:ANGPTL3
1294:Statins
907:5314136
801:(INN).
653:by the
623:History
573:, is a
459:Formula
356:DB15067
322:PubChem
90:)
84: (
82:C10AX18
1915:Portal
1879:WHO-EM
1595:Others
1468:(VLDL)
1385:Niacin
1225:resins
1193:NPC1L1
1104:19 May
1075:
1007:19 May
955:
914:
904:
829:19 May
677:3'—A*—
524:SMILES
434:ChEMBL
423:D11650
416:D11648
311:sodium
117:
1788:Other
1505:(LDL)
1285:Liver
1098:(EMA)
1001:(EMA)
823:(emc)
793:Names
762:= 2'-
544:InChI
313:salt)
1414:VLDL
1410:MTTP
1364:and
1269:and
1106:2020
1073:PMID
1036:2016
1009:2020
953:PMID
912:PMID
831:2020
753:*—5'
635:and
592:for
407:KEGG
387:UNII
168:-2'-
166:ambo
1705:HDL
1701:LDL
1663:LDL
1620:HDL
1447:LDL
1366:LDL
1362:HDL
1302:LDL
1229:LDL
1171:C10
1063:doi
943:doi
939:112
902:PMC
894:doi
861:hdl
731:dmC
719:dmC
715:dmC
695:dmC
513:.05
511:165
485:125
473:320
467:230
326:CID
158:all
119:POM
87:WHO
1941::
1892::
1300:,
1191:,
1127:.
1093:.
1071:.
1059:39
1057:.
1053:.
1027:.
996:.
965:^
951:.
937:.
933:.
910:.
900:.
890:69
888:.
884:.
857:30
855:.
839:^
821:.
749:*—
745:*—
741:*—
737:*—
727:dG
723:dA
711:dT
707:dG
703:dT
699:dT
693:*—
689:*—
685:*—
683:mC
681:*—
646:.
639:.
631:,
497:19
491:19
479:63
126:EU
113:UK
1917::
1707:)
1703:/
1665:)
1661:(
1622:)
1618:(
1449:)
1416:)
1368:)
1304:)
1296:(
1231:)
1227:(
1223:/
1173:)
1169:(
1159:e
1152:t
1145:v
1108:.
1079:.
1065::
1038:.
1011:.
959:.
945::
918:.
896::
869:.
863::
833:.
778:d
772:m
764:O
760:*
751:T
747:A
743:T
739:T
735:T
733:—
729:—
725:—
721:—
717:—
713:—
709:—
705:—
701:—
697:—
691:T
687:T
679:G
596:3
579:O
509:7
494:S
488:P
482:O
476:N
470:H
464:C
309:(
282:O
278:P
274:O
270:P
266:O
262:P
258:O
254:P
250:O
246:P
242:P
238:P
234:P
230:P
226:P
222:P
218:P
214:P
210:P
206:P
202:O
198:P
194:O
190:P
186:O
182:P
178:O
174:P
170:O
164:-
162:P
160:-
128::
115::
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