Asunaprevir

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Asunaprevir are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Asunaprevir?

The molecule Asunaprevir presents a molecular formula of C35H46ClN5O9S and its IUPAC name is 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.

Asunaprevir (BMS-650032) is a potent and selective inhibitor of the HCV NS3/4A protease with IC50 of 0.6 nM.1 It is active against HCV genotypes 1a and 1b in vitro and demonstrates potent antiviral activity in HCV-infected chimpanzees.2,3 Phase I clinical trials in HCV-infected patients have shown that Asunaprevir is well tolerated and achieves rapid and sustained HCV RNA reduction.4.

Asunaprevir is a member of the HCV NS3/4A protease inhibitor class. The HCV NS3/4A protease is essential for HCV replication and is a validated target for antiviral therapy. Asunaprevir inhibits the HCV NS3/4A protease with high potency and selectivity.1 It is active against HCV genotypes 1a and 1b in vitro and demonstrates potent antiviral activity in HCV-infected chimpanzees.2,3.

Asunaprevir is being developed by Bristol-Myers Squibb in collaboration with Astellas Pharma. It is currently in Phase III clinical trials..

The development of Asunaprevir was motivated by the need for more effective and better-tolerated HCV therapies. Current HCV treatments are associated with a number of limitations, including low efficacy, poor tolerability, and the development of resistance.5 Asunaprevir has the potential to overcome these limitations..

Asunaprevir is a potent and selective inhibitor of the HCV NS3/4A protease.1 It is active against HCV genotypes 1a and 1b in vitro and demonstrates potent antiviral activity in HCV-infected chimpanzees.2,3 Asunaprevir is being developed by Bristol-Myers Squibb in collaboration with Astellas Pharma. It is currently in Phase III clinical trials..

The development of Asunaprevir was motivated by the need for more effective and better-tolerated HCV therapies. Current HCV treatments are associated with a number of limitations, including low efficacy, poor tolerability, and the development of resistance.5 Asunaprevir has the potential to overcome these limitations..

Asunaprevir is a potent and selective inhibitor of the HCV NS3/4A protease.1 It is active against HCV genotypes 1a and 1b in vitro and demonstrates potent antiviral activity in HCV-infected chimpanzees.2,3.

Asunaprevir is being developed by Bristol-Myers Squibb in collaboration with Astellas Pharma. It is currently in Phase III clinical trials..

The development of Asunaprevir was motivated by the need for more effective and better-tolerated HCV therapies. Current HCV treatments are associated with a number of limitations, including low efficacy, poor tolerability, and the development of resistance.5 Asunaprevir has the potential to overcome these limitations..

Asunaprevir is a potent and selective inhibitor of the HCV NS3/4A protease.1 It is active against HCV genotypes 1a and 1b in vitro and demonstrates potent antiviral activity in HCV-infected chimpanzees.2,3.

Asunaprevir is being developed by Bristol-Myers Squibb in collaboration with Astellas Pharma. It is currently in Phase III clinical trials..

The development of Asunaprevir was motivated by the need for more effective and better-tolerated HCV therapies. Current HCV treatments are associated with a number of limitations, including low efficacy, poor tolerability, and the development of resistance.5 Asunaprevir has the potential to overcome these limitations..

3D structure

Cartesian coordinates

Geometry of Asunaprevir in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Asunaprevir XRWSZZJLZRKHHD-WVWIJVSJSA-N chemical compound 2D structure molecule svg
Asunaprevir

 

Molecule descriptors

 
IUPAC nametert-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
InChI codeInChI=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
InChI KeyXRWSZZJLZRKHHD-WVWIJVSJSA-N
SMILESC=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H](Oc2ncc(OC)c3ccc(Cl)cc23)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)/C(O)=N/S(=O)(=O)C1CC1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (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
  • 1,1-Dimethylethyl ((1S)-1-(((2S,4R)-4-(7-chloro-4methoxyisoquinolin-1-yloxy)-2- (((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-ethenylcyclopropyl)carbamoyl) pyrrolidin-1-yl)carbonyl)-2,2-dimethylpropyl)carbamate
  • 1,1-dimethylethyl ((1S)-1-{((2S,4R)-4-(7-chloro-4-methoxyisoquinolin-1-yloxy)-2-({(1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-ethenylcyclopropyl}carbamoyl) pyrrolidin-1-yl)carbonyl}-2,2-dimethylpropyl)carbamate
  • 2R9
  • 630420-16-5
  • A857563
  • AMY38775
  • Asunaprevir
  • Asunaprevir (BMS-650032)
  • Asunaprevir (JAN/USAN)
  • Asunaprevir; BMS-650032
  • Asunaprevir;BMS650032;BMS-650032
  • BCP08230
  • BDBM50287594
  • BMS 650032
  • BMS-650032
  • BMS650032
  • BMS650032;(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
  • CS-0674
  • Carbamic acid, [(1S)-1-[[(2S,4R)-4-[(7-chloro-4-methoxy-1-isoquinolinyl)oxy]-2-[[[(1R,2S)-1-[[(cyclopropylsulfonyl)amino]carbonyl]-2-ethenylcyclopropyl]amino]carbonyl]-1-pyrrolidinyl]carbonyl]-2,2-dimethylpropyl]-, 1,1-dimethylethyl ester
  • 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)-
  • 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)-
  • D10093
  • DB11586
  • EX-A386
  • GTPL10882
  • HY-14434
  • MFCD27987900
  • N-(Tert-Butoxycarbonyl)-3-Methyl-L-Valyl-(4r)-4-[(7-Chloro-4-Methoxyisoquinolin-1-Yl)oxy]-N-{(1r,2s)-1-[(Cyclopropylsulfonyl)carbamoyl]-2-Ethenylcyclopropyl}-L-Prolinamide
  • NCGC00378691-02
  • NCGC00378691-05
  • Q4811881
  • S9X0KRJ00S
  • Sunvepratrade
  • TERT-BUTYL ((2S)-1-((2S,4R)-4-((7-CHLORO-4-METHOXYISOQUINOLIN-1-YL)OXY)-2-(((1R,2S)-1-((CYCLOPROPANESULFONYL)CARBAMOYL)-2-ETHENYLCYCLOPROPYL)CARBAMOYL)PYRROLIDIN-1-YL)-3,3-DIMETHYL-1-OXOBUTAN-2-YL)CARBAMATE
  • sunvepra
  • tert-butyl ((S)-1-((2S,4R)-4-((7-chloro-4-methoxyisoquinolin-1-yl)oxy)-2-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)carbamate
  • tert-butyl N-[(1S)-1-[(2S,4R)-4-[(7-chloro-4-methoxy-1-isoquinolyl)oxy]-2-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]carbamoyl]pyrrolidine-1-carbonyl]-2,2-dimethyl-propyl]carbamate
  • 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

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC85540202
  • UNII-S9X0KRJ00S
  • AKOS037515831
  • DTXSID201026065
  • CHEMBL2105735
  • CHEBI:134723
  • SCHEMBL2630655

Physico-Chemical properties

IUPAC nametert-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 formulaC35H46ClN5O9S
Molecular weight748.286
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity196.81
LogP6.5
Topological polar surface area194.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.