Asunaprevir

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
Other names BMS-650032
Identifiers
CAS Number	630420-16-5^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL2105735
ChemSpider	17235944
ECHA InfoCard	100.206.482
KEGG	D10093^Y
PubChem	16076883
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
ATC code	J05AE15 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Asunaprevir (formerly BMS-650032, brand name in Japan and Russia^[1] Sunvepra) is an experimental drug candidate for the treatment of hepatitis C. It is undergoing development by Bristol-Myers Squibb and is currently in Phase III clinical trials.^[2]

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]

References

↑ "Sunvepra™ (asunaprevir) soft gelatin capsules 100 mg. Registration certificate". State Register of Medicines (in Russian). Retrieved 26 August 2015.
↑ "A Phase 3 Study in Combination With BMS-790052 and BMS-650032 in Japanese Hepatitis C Virus (HCV) Patients". ClinicalTrials.gov.
↑ 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.2012.37.4.1789350.
↑ 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.
↑ "Bristol-Myers' Daclatasvir, Asunaprevir Cured 77%: Study". Bloomberg. Apr 19, 2012.
↑ AASLD: Daclatasvir plus Asunaprevir Rapidly Suppresses HCV in Prior Null Responders. Highleyman, L. HIVandHepatitis.com. 8 November 2011.

RNA virus antivirals (primarily J05, also S01AD and D06BB)

Hepatitis C

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir Faldaprevir^‡ Grazoprevir Paritaprevir Simeprevir Telaprevir

NS5A inhibitors (–asvir)	Daclatasvir Elbasvir Ledipasvir MK-3682 MK-8408 Odalasvir^† Ombitasvir Ravidasvir^† Samatasvir^† Velpatasvir

NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Dasabuvir Deleobuvir^§ Filibuvir^§ Setrobuvir^§ Sofosbuvir Radalbuvir^†

Combination drugs	Elbasvir/grazoprevir Ledipasvir/sofosbuvir Ombitasvir/paritaprevir/ritonavir Sofosbuvir/daclatasvir Velpatasvir/sofosbuvir

Picornavirus

viral entry: Pleconaril^†

Anti-influenza agents

Umifenovir

neuraminidase inhibitors/release phase (Oseltamivir
Zanamivir
Peramivir, Laninamivir^†)

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^#

Multiple/unknown	BCX4430^† Favipiravir GS-5734^† Mericitabine^† MK-608^§ NITD008^§ Moroxydine Ribavirin^#/Taribavirin^† Triazavirin

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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Asunaprevir

See also

References