Asunaprevir

Asunaprevir (formerly BMS-650032, brand name in Japan and Russia[1] 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.[2]

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
Preferred 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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.206.482
KEGG
PubChem CID
UNII
InChI
  • 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
SMILES
  • 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
Chemical formula
 C35H46ClN5O9S
Molar mass 748.29 g·mol−1
Pharmacology
J05AP06 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Asunaprevir is an inhibitor of the hepatitis C virus enzyme serine protease NS3.[3]

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.[4][5][6]

See also

References
  1. "Sunvepra™ (asunaprevir) soft gelatin capsules 100 mg. Registration certificate". State Register of Medicines (in Russian). Retrieved 26 August 2015.
  2. "A Phase 3 Study in Combination With BMS-790052 and BMS-650032 in Japanese Hepatitis C Virus (HCV) Patients". ClinicalTrials.gov.
  3. 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.
  4. Lok, A; et al. (2012). "Preliminary Study of Two Antiviral Agents for Hepatitis C Genotype 1". New England Journal of Medicine. 366 (3): 216–224. doi:10.1056/NEJMoa1104430. PMID 22256805.
  5. "Bristol-Myers' Daclatasvir, Asunaprevir Cured 77%: Study". Bloomberg. Apr 19, 2012.
  6. 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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