374:
InChI=1S/C248H355N65O72/c1-16-17-18-19-20-21-22-23-24-25-38-75-193(327)265-118-196(330)304-205(133(15)316)241(378)295-163(104-188(256)322)224(361)283-152(91-127(6)7)216(353)303-175(122-315)232(369)306-204(129(10)11)248(385)313-88-53-74-182(313)239(376)301-172(107-191(259)325)246(383)312-87-50-70-178(312)235(372)291-150(89-125(2)3)209(346)268-120-195(329)274-154(93-135-56-32-27-33-57-135)217(354)296-168(95-137-60-36-29-37-61-137)242(379)308-83-49-72-180(308)237(374)294-167(111-201(339)340)230(367)286-157(98-140-115-261-123-269-140)220(357)277-148(76-78-183(251)317)213(350)282-151(90-126(4)5)215(352)300-173(112-202(341)342)247(384)307-82-47-68-176(307)233(370)273-132(14)208(345)279-153(92-134-54-30-26-31-55-134)210(347)267-119-194(328)271-130(12)206(343)280-160(101-185(253)319)226(363)302-174(121-314)231(368)288-161(102-186(254)320)225(362)299-171(106-190(258)324)245(382)311-86-52-73-181(311)238(375)293-166(110-200(337)338)229(366)285-156(96-138-113-263-144-64-41-39-62-142(138)144)219(356)290-165(109-199(335)336)227(364)284-155(94-136-58-34-28-35-59-136)218(355)298-170(105-189(257)323)244(381)310-85-51-71-179(310)236(373)292-162(103-187(255)321)223(360)275-146(66-43-45-80-249)212(349)289-164(108-198(333)334)228(365)287-158(99-141-116-262-124-270-141)221(358)297-169(97-139-114-264-145-65-42-40-63-143(139)145)243(380)309-84-48-69-177(309)234(371)278-149(77-79-197(331)332)211(348)272-131(13)207(344)281-159(100-184(252)318)222(359)276-147(67-44-46-81-250)214(351)305-203(128(8)9)240(377)266-117-192(260)326/h26-37,39-42,54-65,113-116,123-133,146-182,203-205,263-264,314-316H,16-25,38,43-53,66-112,117-122,249-250H2,1-15H3,(H2,251,317)(H2,252,318)(H2,253,319)(H2,254,320)(H2,255,321)(H2,256,322)(H2,257,323)(H2,258,324)(H2,259,325)(H2,260,326)(H,261,269)(H,262,270)(H,265,327)(H,266,377)(H,267,347)(H,268,346)(H,271,328)(H,272,348)(H,273,370)(H,274,329)(H,275,360)(H,276,359)(H,277,357)(H,278,371)(H,279,345)(H,280,343)(H,281,344)(H,282,350)(H,283,361)(H,284,364)(H,285,366)(H,286,367)(H,287,365)(H,288,368)(H,289,349)(H,290,356)(H,291,372)(H,292,373)(H,293,375)(H,294,374)(H,295,378)(H,296,354)(H,297,358)(H,298,355)(H,299,362)(H,300,352)(H,301,376)(H,302,363)(H,303,353)(H,304,330)(H,305,351)(H,306,369)(H,331,332)(H,333,334)(H,335,336)(H,337,338)(H,339,340)(H,341,342)/t130-,131-,132-,133+,146-,147-,148-,149-,150-,151-,152-,153-,154-,155-,156-,157-,158-,159-,160-,161-,162-,163-,164-,165-,166-,167-,168-,169-,170-,171-,172-,173-,174-,175-,176-,177-,178-,179-,180-,181-,182-,203-,204-,205-/m0/s1
332:
354:
CCCCCCCCCCCCCC(=O)NCC(=O)N(C(=O)N(CC(N)=O)C(=O)N(CC(C)C)C(=O)N(CO)C(=O)N(C(=O)N1CCC1C(=O)N(CC(N)=O)C(=O)N1CCC1C(=O)N(CC(C)C)C(=O)NCC(=O)N(Cc1ccccc1)C(=O)N(Cc1ccccc1)C(=O)N1CCC1C(=O)N(CC(=O)O)C(=O)N(Cc1ccn1)C(=O)N(CCC(N)=O)C(=O)N(CC(C)C)C(=O)N(CC(=O)O)C(=O)N1CCC1C(=O)N(C)C(=O)N(Cc1ccccc1)C(=O)NCC(=O)N(C)C(=O)N(CC(N)=O)C(=O)N(CO)C(=O)N(CC(N)=O)C(=O)N(CC(N)=O)C(=O)N1CCC1C(=O)N(CC(=O)O)C(=O)N(Cc1cc2ccccc12)C(=O)N(CC(=O)O)C(=O)N(Cc1ccccc1)C(=O)N(CC(N)=O)C(=O)N1CCC1C(=O)N(CC(N)=O)C(=O)N(CCCCN)C(=O)N(CC(=O)O)C(=O)N(Cc1ccn1)C(=O)N(Cc1cc2ccccc12)C(=O)N1CCC1C(=O)N(CCC(=O)O)C(=O)N(C)C(=O)N(CC(N)=O)C(=O)N(CCCCN)C(=O)N(C(=O)NCC(N)=O)C(C)C)C(C)C)(C)O
31:
1822:
414:
Bulevirtide works by attaching to and blocking a receptor (target) through which the hepatitis delta and hepatitis B viruses enter liver cells. By blocking the entry of the virus into the cells, it limits the ability of HDV to replicate and its effects in the body, reducing symptoms of the disease.
581:
Pre-clinical data in mice suggests that pharmacological inhibition of NTCP-mediated bile salt uptake may also be effective to lower hepatic bile salt accumulation in cholestatic conditions. This reduces hepatocellular damage. An increased ratio of phospholipid to bile salts seen in bile upon NTCP
1007:
Na+ -taurocholate cotransporting polypeptide inhibition has hepatoprotective effects in cholestasis in mice. Slijepcevic D, Roscam Abbing RLP, Fuchs CD, Haazen LCM, Beuers U, Trauner M, Oude
Elferink RPJ, van de Graaf SFJ. Hepatology. 2018 Sep;68(3):1057-1069. doi:
889:
Volz T, Allweiss L, Ben MBarek M, Warlich M, Lohse AW, Pollok JM, et al. (May 2013). "The entry inhibitor
Myrcludex-B efficiently blocks intrahepatic virus spreading in humanized mice previously infected with hepatitis B virus".
578:
The drug is also effective against hepatitis D because the hepatitis D virus uses the same entry receptor as HBV and is only effective in the presence of a hepatitis B virus infection.
120:
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Bulevirtide is indicated for the treatment of chronic hepatitis delta virus (HDV) infection in plasma (or serum) HDV-RNA positive adult patients with compensated
75:
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Text was copied from this source which is copyright
European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
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1020:"Blocking Sodium-Taurocholate Cotransporting Polypeptide Stimulates Biliary Cholesterol and Phospholipid Secretion in Mice"
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inhibition may further contribute to the protective effect as bile salts are less toxic in presence of phospholipids.
411:
The most common side effects include raised levels of bile salts in the blood and reactions at the site of injection.
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via their sodium/bile acid cotransporter (NTCP) and subsequently entering the cells. Myrcludex B is a synthetic N-
105:
549:
1077:
1092:
1018:
Roscam Abbing RL, Slijepcevic D, Donkers JM, Havinga R, Duijst S, Paulusma CC, et al. (January 2020).
859:
198:
763:
599:
Deterding K, Wedemeyer H (2019). "Beyond
Pegylated Interferon-Alpha: New Treatments for Hepatitis Delta".
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61:
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68:
733:
695:"Hepcludex 2 mg powder for solution for injection - Summary of Product Characteristics (SmPC)"
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790:"Intact plasma quantification of the large therapeutic lipopeptide bulevirtide"
397:
1107:
612:
1836:
1320:
957:
788:
Sauter M, Blank A, Stoll F, Lutz N, Haefeli WE, Burhenne J (September 2021).
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501:
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473:
418:
Bulevirtide was approved for medical use in the
European Union in July 2020.
22:
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pre-S1 that can also dock to NTCP, blocking the virus's entry mechanism.
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485:
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449:
426:
Bulevirtide is a 47-amino acid peptide with the following sequence:
1253:
941:"Management of hepatitis delta: Need for novel therapeutic options"
235:
227:
178:
993:
Spreitzer H (14 September 2015). "Neue
Wirkstoffe – Myrcludex B".
331:
1707:
1345:
1340:
489:
469:
457:
445:
643:"Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024"
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497:
465:
461:
246:
30:
888:
505:
322:
1303:
1234:
1145:
572:
218:
1810:
519:
CO-GTNLSVPNPLGFFPDHQLDPAFGANSNNPDWDFNPNKDHWPEANKVG-NH
787:
598:
552:, blocking both HBV and HDV viruses from entering
1834:
728:
726:
724:
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29:
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956:
857:
813:
206:
186:
1835:
794:Analytical and Bioanalytical Chemistry
673:Therapeutic Goods Administration (TGA)
548:Bulevirtide binds and inactivates the
543:
140:
127:
1081:
932:
669:"Hepcludex (Gilead Sciences Pty Ltd)"
492:-Phe-Gly-Ala-Asn-Ser-Asn-Asn-Pro-Asp-
421:
254:
882:
768:Union Register of medicinal products
87:
1422:Sofosbuvir/velpatasvir/voxilaprevir
234:
226:
13:
1066:: CS1 maint: overridden setting (
924:: CS1 maint: overridden setting (
14:
1869:
1407:Ombitasvir/paritaprevir/ritonavir
945:World Journal of Gastroenterology
870:from the original on 15 June 2020
114:
1820:
995:Ă–sterreichische Apothekerzeitung
939:Abbas Z, Abbas M (August 2015).
288:
282:
1001:
838:"Summary of opinion: Hepcludex"
764:"Hepcludex Product information"
647:Federal Register of Legislation
538:
526:
379:Key:WQNDXLHKAMIGEX-WOAPPVHJSA-N
851:
830:
781:
756:
687:
661:
635:
592:
550:sodium/bile acid cotransporter
294:
276:
1:
1148:protease inhibitors (–previr)
585:
567:pre-S1 for docking to mature
400:for the treatment of chronic
858:Francisco EM (29 May 2020).
392:, sold under the brand name
7:
10:
1874:
997:(in German) (19/2015): 12.
904:10.1016/j.jhep.2012.12.008
806:10.1007/s00216-021-03384-7
266:Chemical and physical data
1771:
1736:
1655:
1601:
1573:
1566:
1476:
1452:
1434:
1384:
1302:
1233:
1140:
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864:European Medicines Agency
845:European Medicines Agency
739:European Medicines Agency
613:10.24875/AIDSRev.19000080
362:
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245:
217:
197:
177:
157:
152:
104:
99:
74:
60:
52:
42:
37:
28:
1534:neuraminidase inhibitors
1397:Glecaprevir/pibrentasvir
958:10.3748/wjg.v21.i32.9461
1737:Multiple/Unknown/Other
1506:adamantane derivatives
1417:Sofosbuvir/velpatasvir
1412:Sofosbuvir/daclatasvir
1605:inhibitors (–trelvir)
1593:Peginterferon alfa-2b
1588:Peginterferon alfa-2a
1402:Ledipasvir/sofosbuvir
892:Journal of Hepatology
504:-Ala-Asn-Lys-Val-Gly-
496:-Asp-Phe-Asn-Pro-Asn-
1843:Anti–RNA virus drugs
1392:Elbasvir/grazoprevir
404:(in the presence of
398:antiviral medication
16:Antiviral medication
1309:inhibitors (–buvir)
1237:inhibitors (–asvir)
675:. 13 September 2024
544:Mechanism of action
136:(Prescription only)
123:(Prescription only)
25:
1798:Never to phase III
1656:RNA pol inhibitors
1583:Interferon alfa 2b
1488:Baloxavir marboxil
422:Structural formula
21:
1808:
1807:
1767:
1766:
1430:
1429:
1385:Combination drugs
1036:10.1002/hep.30792
1008:10.1002/hep.29888
951:(32): 9461–9465.
800:(22): 5645–5654.
563:uses its surface
561:hepatitis B virus
500:-Asp-His-Trp-Pro-
472:-Asn-Pro-Leu-Gly-
387:
386:
333:Interactive image
144:
131:
118:
56:MyrB, Myrcludex-B
1865:
1858:Entry inhibitors
1825:
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1823:
1816:
1571:
1570:
1567:Multiple/general
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748:
734:"Hepcludex EPAR"
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33:
26:
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1848:Viral hepatitis
1833:
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1788:Clinical trials
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701:. 30 March 2022
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1728:Valopicitabine
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1307:RNA polymerase
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1030:(1): 247–258.
1010:
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931:
898:(5): 861–867.
881:
850:
847:. 28 May 2020.
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607:(3): 126–134.
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1538:release phase
1535:
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1510:M2 inhibitors
1507:
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1321:Bemnifosbuvir
1319:
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743:. 26 May 2020
742:
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649:. 30 May 2024
648:
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583:
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562:
557:
555:
551:
536:
534:
533:liver disease
524:
510:
503:
499:
495:
491:
488:-Leu-Asp-Pro-
487:
483:
479:
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471:
467:
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256:ChEMBL4297711
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145: Rx-only
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59:
55:
51:
47:
45:
41:
38:Clinical data
36:
32:
27:
19:
1853:Orphan drugs
1703:Molnupiravir
1698:Mericitabine
1668:Deuremidevir
1642:Simnotrelvir
1627:Nirmatrelvir
1617:Ibuzatrelvir
1603:3CL protease
1532:
1504:
1461:
1454:Picornavirus
1443:
1376:Uprifosbuvir
1274:Pibrentasvir
1225:Voxilaprevir
1195:Paritaprevir
1062:cite journal
1027:
1023:
1013:
1003:
994:
948:
944:
934:
920:cite journal
895:
891:
884:
872:. Retrieved
863:
853:
832:
797:
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783:
771:. Retrieved
767:
758:
745:. Retrieved
737:
703:. Retrieved
698:
689:
679:15 September
677:. Retrieved
672:
663:
651:. Retrieved
646:
637:
604:
601:AIDS Reviews
600:
594:
580:
577:
558:
547:
539:Pharmacology
530:
527:Medical uses
428:
425:
417:
413:
410:
393:
389:
388:
168:2012558-47-1
106:Legal status
100:Legal status
69:Subcutaneous
18:
1784:from market
1749:Merimepodib
1723:Triazavirin
1718:Taribavirin
1678:Galidesivir
1673:Favipiravir
1637:Rupintrivir
1622:Lufotrelvir
1612:Ensitrelvir
1557:Laninamivir
1543:Oseltamivir
1525:Rimantadine
1463:viral entry
1444:Bulevirtide
1436:Hepatitis D
1294:Velpatasvir
1249:Daclatasvir
1244:Coblopasvir
1220:Vedroprevir
1190:Narlaprevir
1185:Grazoprevir
1180:Glecaprevir
1175:Faldaprevir
1155:Asunaprevir
1133:Hepatitis C
1114:(primarily
860:"Hepcludex"
569:liver cells
565:lipopeptide
554:hepatocytes
406:hepatitis B
402:hepatitis D
390:Bulevirtide
316: g·mol
153:Identifiers
53:Other names
44:Trade names
23:Bulevirtide
1837:Categories
1759:Presatovir
1754:Moroxydine
1688:Remdesivir
1646:+ritonavir
1631:+ritonavir
1575:Interferon
1520:Amantadine
1515:Adapromine
1498:Umifenovir
1468:Pleconaril
1371:Radalbuvir
1366:TMC-647055
1356:Sofosbuvir
1351:Setrobuvir
1331:Deleobuvir
1316:Beclabuvir
1289:Samatasvir
1279:Ravidasvir
1269:Ombitasvir
1259:Ledipasvir
1215:Vaniprevir
1210:Telaprevir
1205:Sovaprevir
1200:Simeprevir
1170:Danoprevir
1165:Ciluprevir
1160:Boceprevir
1112:antivirals
1024:Hepatology
586:References
321:3D model (
305:Molar mass
208:WKM56H3TLB
159:CAS Number
1794:Phase III
1782:Withdrawn
1713:Ribavirin
1683:GS-441524
1553:Peramivir
1548:Zanamivir
1493:Pimodivir
1479:influenza
1361:Tegobuvir
1336:Filibuvir
1326:Dasabuvir
1264:Odalasvir
1109:RNA virus
747:12 August
629:202674681
476:-Phe-Pro-
394:Hepcludex
62:Routes of
48:Hepcludex
1827:Medicine
1284:Ruzasvir
1254:Elbasvir
1054:31136002
977:26327754
912:23246506
874:6 August
868:Archived
824:34018034
621:31532397
573:acylated
396:, is an
179:DrugBank
76:ATC code
1708:NITD008
1346:IDX-184
1341:GS-6620
1118:, also
1045:7003915
968:4548107
815:8410713
773:3 March
653:10 June
272:Formula
188:DB15248
92:)
86: (
84:J05AX28
1813:Portal
1777:WHO-EM
1693:MK-608
1663:CMX521
1481:agents
1052:
1042:
975:
965:
910:
822:
812:
705:1 July
627:
619:
347:SMILES
247:ChEMBL
236:D11878
228:D11877
132:
119:
1744:EICAR
1477:Anti-
1124:D06BB
1120:S01AD
841:(PDF)
741:(EMA)
699:(emc)
625:S2CID
367:InChI
323:JSmol
1304:NS5B
1235:NS5A
1122:and
1068:link
1050:PMID
973:PMID
926:link
908:PMID
876:2020
820:PMID
775:2023
749:2020
707:2022
681:2024
655:2024
617:PMID
559:The
314:.951
219:KEGG
199:UNII
1142:NS3
1116:J05
1040:PMC
1032:doi
963:PMC
953:doi
900:doi
810:PMC
802:doi
798:413
609:doi
502:Glu
498:Lys
494:Trp
490:Ala
486:Gln
482:His
478:Asp
474:Phe
470:Pro
466:Val
462:Ser
458:Leu
454:Asn
450:Thr
446:Gly
434:(CH
408:).
312:398
286:355
280:248
134:POM
89:WHO
1839::
1790::
1555:,
1146:4A
1064:}}
1060:{{
1048:.
1038:.
1028:71
1026:.
1022:.
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961:.
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918:{{
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896:58
894:.
866:.
862:.
843:.
818:.
808:.
796:.
792:.
766:.
736:.
715:^
697:.
671:.
645:.
623:.
615:.
605:21
603:.
556:.
535:.
523:)
517:27
513:13
511:(C
506:NH
442:CO
440:12
430:CH
298:72
292:65
141:EU
128:UK
121:S4
115:AU
1815::
1648:)
1644:(
1633:)
1629:(
1559:)
1541:(
1536:/
1527:)
1513:(
1508:/
1465::
1144:/
1126:)
1101:e
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1087:v
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1034::
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902::
878:.
826:.
804::
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709:.
683:.
657:.
631:.
611::
521:2
515:H
508:2
484:-
480:-
468:-
464:-
460:-
456:-
452:-
448:-
444:-
438:)
436:2
432:3
325:)
310:5
295:O
289:N
283:H
277:C
143::
130::
117::
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