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| PubChem = 16076883
| PubChem = 16076883
| ChemSpiderID = 17235944
| ChemSpiderID = 17235944
| ChEBI = 134723
| DrugBank = DB11586
| IUPHAR_ligand = 10882
| ChEMBL = 2105735
| ChEMBL = 2105735
| KEGG = D10093
| KEGG = D10093
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| Legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2015 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/prescription-medicines-registration-new-chemical-entities-australia-2015 | access-date=10 April 2023}}</ref>
| Legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2015 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/prescription-medicines-registration-new-chemical-entities-australia-2015 | access-date=10 April 2023}}</ref>
| Legal_CA = Rx-only
| Legal_CA = Rx-only
| Legal_CA_comment = <ref>{{cite web | title=Health Canada New Drug Authorizations: 2016 Highlights | website=[[Health Canada]] | date=14 March 2017 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-canada-new-drug-authorizations-2016-highlights.html | access-date=7 April 2024}}</ref>
| Legal_CA_comment =
| Legal_NZ =
| Legal_NZ =
| Legal_NZ_comment =
| Legal_NZ_comment =
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| Pregnancy_AU_comment =
| Pregnancy_AU_comment =
| Dependence_liability =
| Dependence_liability =
| Addiction_liability =
| AdminRoutes =
| AdminRoutes =
| Bioavail =
| Bioavail =
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[[Category:Cyclopropanes]]
[[Category:Cyclopropanes]]
[[Category:CYP2D6 inhibitors]]
[[Category:CYP2D6 inhibitors]]
[[Category:Experimental drugs]]
[[Category:Experimental antiviral drugs]]
[[Category:Isoquinolines]]
[[Category:Isoquinolines]]
[[Category:NS3/4A protease inhibitors]]
[[Category:NS3/4A protease inhibitors]]
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[[Category:Sulfonamides]]
[[Category:Sulfonamides]]
[[Category:Tert-butyl compounds]]
[[Category:Tert-butyl compounds]]
[[Category:Methoxy compounds]]




Revision as of 05:20, 7 April 2024

Asunaprevir
Names
IUPAC name
3-Methyl-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-valyl-(4R)-4-[(7-chloro-4-methoxy-1-isoquinolinyl)oxy]-N-{(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-vinylcyclopropyl}-L-prolinamide
Systematic IUPAC name
tert-Butyl {(2S)-1-[(32S,34R,61R,62S)-17-chloro-62-ethenyl-14-methoxy-4,7,9,9-tetraoxo-2-oxa-9λ6-thia-5,8-diaza-1(1)-isoquinolina-3(4,2)-pyrrolidina-6(1,1),10(1)-dicyclopropadecaphan-31-yl]-3,3-dimethyl-1-oxobutan-2-yl}carbamate
Other names
BMS-650032
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.206.482 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
    Key: XRWSZZJLZRKHHD-WVWIJVSJSA-N
  • InChI=1/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
    Key: XRWSZZJLZRKHHD-WVWIJVSJBJ
  • O=C(N5[C@H](C(=O)N[C@@]2(C(=O)NS(=O)(=O)C1CC1)[C@H](\C=C)C2)C[C@@H](Oc3ncc(OC)c4c3cc(Cl)cc4)C5)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C
Properties
C35H46ClN5O9S
Molar mass 748.29 g·mol−1
Pharmacology
J05AP06 (WHO)
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Asunaprevir (formerly BMS-650032, brand name in Japan and Russia[3] Sunvepra) is an experimental drug candidate for the treatment of hepatitis C. It was undergoing development by Bristol-Myers Squibb and has completed Phase III clinical trials in 2013.[4]

Asunaprevir is an inhibitor of the hepatitis C virus enzyme serine protease NS3.[5] Asunaprevir is being tested in combination with pegylated interferon and ribavirin, as well as in interferon-free regimens with other direct-acting antiviral agents including daclatasvir.[6][7][8]

References

  1. ^ "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
  2. ^ "Health Canada New Drug Authorizations: 2016 Highlights". Health Canada. 14 March 2017. Retrieved 7 April 2024.
  3. ^ "Sunvepra (asunaprevir) soft gelatin capsules 100 mg. Registration certificate". State Register of Medicines (in Russian). Retrieved 26 August 2015.
  4. ^ "A Phase 3 Study in Combination With BMS-790052 and BMS-650032 in Japanese Hepatitis C Virus (HCV) Patients". ClinicalTrials.gov. 23 September 2015.
  5. ^ C. Reviriego (2012). "Asunaprevir. HCV serine protein NS3 inhibitor, Treatment of hepatitis C virus". Drugs of the Future. 37 (4): 247–254. doi:10.1358/dof.2012.037.04.1789350.
  6. ^ Lok AS, Gardiner DF, Lawitz E, Martorell C, Everson GT, Ghalib R, et al. (January 2012). "Preliminary study of two antiviral agents for hepatitis C genotype 1". The New England Journal of Medicine. 366 (3): 216–24. doi:10.1056/NEJMoa1104430. PMID 22256805.
  7. ^ "Bristol-Myers' Daclatasvir, Asunaprevir Cured 77%: Study". Bloomberg. 19 April 2012.
  8. ^ AASLD: Daclatasvir plus Asunaprevir Rapidly Suppresses HCV in Prior Null Responders Archived 2015-02-08 at the Wayback Machine. Highleyman, L. HIVandHepatitis.com. 8 November 2011.


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