Ciluprevir
Basic information
- CAS
300832-84-2- Standard SMILES
COc1ccc2c(O[C@@H]3C[C@H]4C(=O)N[C@]5(C(=O)O)C[C@H]5/C=C\CCCCC[C@H](NC(=O)OC5CCCC5)C(=O)N4C3)cc(-c3csc(NC(C)C)n3)nc2c1- InChIKey
PJZPDFUUXKKDNB-KNINVFKUSA-N- Molecular formula
- C40H50N6O8S
- Average molar mass
- 774.9 g/mol
- Monoisotopic mass
- 774.34108375
Overview
The compound, named BILN 2061, is an orally active inhibitor of the HCV NS3 protease and the first member of this new drug class to be tested in humans.
Names & identifiers
- Preferred name
- Ciluprevir
- IUPAC
- (1S,4R,6S,7Z,14S,18R)-14-(cyclopentyloxycarbonylamino)-18-[7-methoxy-2-[2-(propan-2-ylamino)-1,3-thiazol-4-yl]quinolin-4-yl]oxy-2,15-dioxo-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid
- English name
- BILN-2061
- Molecular formula
- C40H50N6O8S
- Molecular weight
- 774.93
Names & synonyms
CiluprevirBILN-2061300832-84-2BILN 2061BILN 2061 ZWBILN-2061-ZWBILN206175C8DU40T0DTXSID50870316(2R,6S,12Z,13aS,14aR,16aS)-6-(((Cyclopentyloxy)carbonyl)amino)-2-((7-methoxy-2-(2-((1-methylethyl)amino)thiazol-4-yl)quinolin-4-yl)oxy)-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa(e)pyrrolo(1,2-a)(1,4)diazacyclopentadecine-14a(5H)-carboxylic acidciluprevirum(2R,6S,12Z,13aS,14aR,16aS)-6-[[(Cyclopentyloxy)carbonyl]amino]-2-[[7-methoxy-2-[2-[(1-methylethyl)amino]thiazol-4-yl]quinolin-4-yl]oxy]-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[E]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylic acid
Show more names
BILN 2061ZWCiluprevir (BILN 2061)Ciluprevir (BILN 2061,BILN 2061ZW)(2R,6S,12Z,13aS,14aR,16aS)-6-[[(Cyclopentyloxy)carbonyl]amino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-2-[[7-methoxy-2-[2-[(1-methylethyl)amino]-4-thiazolyl]-4-quinolinyl]oxy]-5,16-dioxocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a
Properties
Computed structural properties
- XLogP
- 6.4
- Topological polar surface area
- 210 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 10
- Heavy atoms
- 55
- Formal charge
- 0
- Complexity
- 1,420
Physicochemical properties
- Density
- 1.37 · 1.37
- solubility
- Soluble in DMSO
- form
- Powder
- pka
- 3.32 · 3.32±0.60(Predicted)
- FDA UNII
- 75 C8DU40T0 · 75C8DU40T0
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Mechanism of Action
A distinguishing feature of the BILN 2061 inhibitor series is the presence of C-terminal carboxylic acid functionality. This provides exquisite selectivity with respect to other proteases, a property not easily attained with more conventional classes of covalent, reversible serine protease inhibitors. BILN 2061 blocks NS3 protease-dependent polyprotein processing in HCV replicon-containing cells. It is orally bioavailable in various animal species.
Applications
UsesTreatment of Hepatitis C infection.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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