Asunaprevir

Category	HCV Protease
CAS	630420-16-5
Description	Asunaprevir is a potent hepatitis C virus (HCV) non-structural protein protease inhibitor currently in Phase III clinical trials for the treatment of HCV infection.

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Product Information

Synonyms	BMS-650032; BMS 650032; BMS650032; Asunaprevir. brand name: Sunvepra
IUPAC Name	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
Molecular Weight	748.29
Molecular Formula	C35H46ClN5O9S
Canonical SMILES	CC(C)(C)C(C(=O)N1CC(CC1C(=O)NC2(CC2C=C)C(=O)NS(=O)(=O)C3CC3)OC4=NC=C(C5=C4C=C(C=C5)Cl)OC)NC(=O)OC(C)(C)C
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
InChIKey	XRWSZZJLZRKHHD-WVWIJVSJSA-N
Melting Point	145-155 °C
Purity	>98%
Density	1.4±0.1 g/cm3
Solubility	In Vitro: DMSO: ≥ 42.9 mg/mL (57.33 mM)
Appearance	Solid powder
Application	Protease Inhibitors
Storage	Powder: -20°C 3 years 4°C 2 years In solvent: -80°C 6 months -20°C 1 months
Animal Admin	Mice receive Asunaprevir (ASV) by oral gavage. Blood samples are obtained by retro-orbital bleeding at 0.25, 0.5, 1, 3, 6, 8, and 24 h after dosing. Livers and brains are also removed from mice at the terminal sampling points. Serial blood samples are obtained from the jugular vein predosing (0 h) and at 0.25, 0.5, 0.75, 1, 2, 4, 6, 8, 24, and 48 h postdosing. To assess tissue exposure, rats are orally administered ASV, and blood, liver, and heart samples from two rats/group are obtained at 0.17, 0.5, 1, 2, 4, 6, 8, 24, 48, and 72 h after dosing.
Complexity	1470
Exact Mass	747.270447
Index Of Refraction	1.616
In Vitro	Populations of resistant colonies are markedly reduced when cells are treated with a combination of DCV and Asunaprevir. Asunaprevir (ASV) inhibits the NS3 proteolytic activity of genotype 1a (H77 strain) and genotype 1b (J4L6S strain), with IC50s of 0.7 and 0.3 nM, respectively. The EC50s of ASV against replicons encoding the NS3 protease domains representing genotypes 1a, 1b, and 4a, range from 1.2 to 4.0 nM. Replicon cells are maintained under selective pressure with asunaprevir at concentrations of 10 and 30 times the EC50 values (50 or 150 nM final concentrations, respectively).
In Vivo	Asunaprevir displays a hepatotropic disposition in several animal species. Twenty-four hours postdose, liver exposures across all species tested are ≥110-fold above the inhibitor EC50 observed with HCV genotype-1 replicons.
PSA	201.18000
Target	IC50: 0.2 nM-3.5 nM (HCV NS3 protease)
XLogP3-AA	4.9