Narlaprevir
(1R,2S,5S)-3-[(2S)-2-[[1-(tert-butylsulfonylmethyl)cyclohexyl]carbamoylamino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
Molecular Identity
Narlaprevir
(1R,2S,5S)-3-[(2S)-2-[[1-(tert-butylsulfonylmethyl)cyclohexyl]carbamoylamino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
PubChem CID: 11857239
Narlaprevir is an azabicyclohexane that is (1R,5S)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane substituted by [(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]aminoacyl and N-({1-[(tert-butylsulfonyl)methyl]cyclohexyl}carbamoyl)-3-methyl-L-valyl groups at positions 2S and 3, respectively. It is a hepatitis C virus (HCV) NS3/4A serine protease inhibitor (Ki = 6 nM) that is used for the treatment of chronic hepatitis C. It has a role as an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, an anticoronaviral agent, an antiviral drug and a hepatitis C protease inhibitor. It is a secondary carboxamide, a tertiary carboxamide, an azabicyclohexane, a sulfone, a pyrrolidinecarboxamide, a member of ureas and a member of cyclopropanes.
2D Structure
Properties
C36H61N5O7S
Molecular Formula
708.00
Molecular Weight
g/mol
707.4292
Exact Mass
Da
5.4
XLogP
Above Lipinski threshold
179
TPSA
May have limited oral absorption
4
H-Bond Donors
7
H-Bond Acceptors
1400
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Narlaprevir865466-24-6SCH 900518SCH-900518SCH900518Arlansanarlaprevirum2857LA2O07CHEBI:173104DTXSID801025746(1R,2S,5S)-3-[(2S)-2-[[1-(tert-butylsulfonylmethyl)cyclohexyl]carbamoylamino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide(1R,2S,5S)-3-((2S)-2-((1-(tert-butylsulfonylmethyl)cyclohexyl)carbamoylamino)-3,3-dimethylbutanoyl)-N-((3S)-1-(cyclopropylamino)-1,2-dioxoheptan-3-yl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexane-2-carboxamideRefChem:927513DTXCID001510010(1R,2S,5S)-3-(N-(((1-((tert-butylsulfonyl)methyl)cyclohexyl)amino)carbonyl)-3-methyl-l-valyl)-N-((1s)-1-((cyclopropylamino)(oxo)acetyl)pentyl)-6,6-dimethyl-3-azabicyclo(3.1.0)hexane-2-carboxamide
Data from PubChem (NCBI)
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