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Asunaprevir

Asunaprevir Structure
CAS No.
630420-16-5
Chemical Name:
Asunaprevir
Synonyms
CS-1413;BMS 650032;Asunaprevir;Asunaprevir API;Asunaprevir,≥98%;Asunaprevir USP/EP/BP;BMS 650032/Asunaprevir;Asunaprevir (BMS-650032);Asunaprevir (10mM in DMSO);BMS-650032; BMS 650032; BMS650032
CBNumber:
CB92614356
Molecular Formula:
C35H46ClN5O9S
Molecular Weight:
748.29
MOL File:
630420-16-5.mol
Modify Date:
2023/6/30 15:45:59

Asunaprevir Properties

Melting point 149-150oC
Density 1.37
storage temp. -20°C Freezer, Under inert atmosphere
solubility DMSO (Slightly), Methanol (Slightly, Heated)
form Solid
pka 4.49±0.40(Predicted)
color White to Off-White

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338

Asunaprevir Chemical Properties,Uses,Production

Description

Sold under the trade name Sunvepra®, asunaprevir received approval in Japan as part of a combination treatment for the hepatitis C virus (HCV). Working in concert with daclatasvir (IX) (vide infra), asunaprevir is a unique treatment for HCV, as it is free from both interferon and ribavirin and is administered orally. This direct-acting anti-viral, which was developed by Bristol–Myers Squibb (BMS), works as an NS3/4A protease inhibitor, representing a valuable treatment option for patient populations who are unable to receive, or do not respond to, the standard course of treatment—peginterferon/ribavirin.

Enzyme inhibitor

This highly selective HCV antiviral (FW = 748.29 g/mol; CAS 630420-16- 5; Symbol: ASV), also named BMS-650032, targets NS3 protease, a serine proteinase required for Hepatitis C Virus (HCV) polyprotein processing, showing good antiviral activity against replicons based on HCV Genotype 1a (EC50 = 4 nM), Genotype 1b (EC50 = 1.2 nM), Genotype 4 (EC50 = 1.8 nM), Genotype 5 (EC50 = 1.7 nM), and Genotype 6 (EC50 = 0.9 nM). It is far less effective against Genotype 2 (EC50 = 67 nM) and Genotype 3 (EC50 = >1100 nM). Asunaprevir is a peptidomimetic that occupies the active site, inhibiting the HCV NS3/4A serine protease, with little or no action against related viruses. The average Ki for ASV is approximately 0.4 nM and 0.2 nM for Genotype 1a and Genotype 1b, respectively. Its acylsulfonamide moeity interacts noncovalently with the NS3 protease – unlike telaprevir’s α-ketoamide moiety, which is linked covalently to NS3/4A’s catalytic serine and reverses slowly over time. ASV exhibits an excellent selectivity index (>40,000x) against all serine/cysteine proteases evaluated, including human leukocyte elastase, porcine pancreatic elastase, and three members of the chymotrypsin family. Although ASV shows a low barrier to resistance, it can be combined with daclatasvir to achieve a very high rate of viral eradication in both na?ve and treatment-experienced patients, showing a sustained virological response rate of 80%-90%.

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Asunaprevir Spectrum

(1R,2S)-N-[(1,1-Dimethylethoxy)carbonyl]-3-methyl-L-valyl-(4R)-4-[(7-chloro-4-methoxy-1-isoquinolinyl)oxy]-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethenylcyclopropanecarboxamide Asunaprevir BMS 650032 Asunaprevir (BMS-650032) BMS 650032/Asunaprevir Asunaprevir API tert-butyl N-[(2S)-1-[(2S,4R)-4-(7-chloro-4-methoxyisoquinolin-1-yl)oxy-2-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]pyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate BMS-650032; BMS 650032; BMS650032 CS-1413 tert-Butyl ((2S)-1-((2S)-2-(((1R,2S)-1-amino-2-vinylcyclopropane-1-carbonyl)(cyclopropylsulfonyl)carbamoyl)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate Asunaprevir,≥98% Cyclopropanecarboxamide, N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-L-valyl-(4R)-4-[(7-chloro-4-methoxy-1-isoquinolinyl)oxy]-L-prolyl-1-amino-N-(cyclopropylsulfonyl)-2-ethenyl-, (1R,2S)- Asunaprevir USP/EP/BP Asunaprevir (10mM in DMSO) 630420-16-5 C35H46ClN5O9S API