vaniprevir   Click here for help

GtoPdb Ligand ID: 11570

Synonyms: analog 35b [PMID: 20163176] | MK-7009 | MK7009 | Vanihep®
Approved drug PDB Ligand
vaniprevir is an approved drug (Japan 2014)
Compound class: Synthetic organic
Comment: Vaniprevir (MK-7009) is a non-covalent competitive, macrocyclic hepatitis C virus (HCV, genotype 1a and 1b) NS3/4A protease inhibitor [2-3]. It has also been reported to inhibit SARS CoV-2 papain-like protease (PL-pro) in vitro [1].
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 14
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 188.9
Molecular weight 757.37
XLogP 4.72
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES CC[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@@H](NC(=O)OCC(C)(C)CCCCc1c3CN(C(=O)O2)Cc3ccc1)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1
Isomeric SMILES CC[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@@H](NC(=O)OCC(C)(C)CCCCc1c3CN(C(=O)O2)Cc3ccc1)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1
InChI InChI=1S/C38H55N5O9S/c1-7-25-18-38(25,33(46)41-53(49,50)27-14-15-27)40-31(44)29-17-26-20-43(29)32(45)30(36(2,3)4)39-34(47)51-22-37(5,6)16-9-8-11-23-12-10-13-24-19-42(21-28(23)24)35(48)52-26/h10,12-13,25-27,29-30H,7-9,11,14-22H2,1-6H3,(H,39,47)(H,40,44)(H,41,46)/t25-,26-,29+,30-,38-/m1/s1
InChI Key KUQWGLQLLVFLSM-ONAXAZCASA-N
References
1. Bafna K, White K, Harish B, Rosales R, Ramelot TA, Acton TB, Moreno E, Kehrer T, Miorin L, Royer CA et al.. (2021)
Hepatitis C virus drugs that inhibit SARS-CoV-2 papain-like protease synergize with remdesivir to suppress viral replication in cell culture.
Cell Rep, 35 (7): 109133. [PMID:33984267]
2. Lawitz E, Sulkowski M, Jacobson I, Kraft WK, Maliakkal B, Al-Ibrahim M, Gordon SC, Kwo P, Rockstroh JK, Panorchan P et al.. (2013)
Characterization of vaniprevir, a hepatitis C virus NS3/4A protease inhibitor, in patients with HCV genotype 1 infection: safety, antiviral activity, resistance, and pharmacokinetics.
Antiviral Res, 99 (3): 214-20. [PMID:23747481]
3. McCauley JA, McIntyre CJ, Rudd MT, Nguyen KT, Romano JJ, Butcher JW, Gilbert KF, Bush KJ, Holloway MK, Swestock J et al.. (2010)
Discovery of vaniprevir (MK-7009), a macrocyclic hepatitis C virus NS3/4a protease inhibitor.
J Med Chem, 53 (6): 2443-63. [PMID:20163176]
4. Rodriguez-Torres M, Stoehr A, Gane EJ, Serfaty L, Lawitz E, Zhou A, Bourque M, Bhanja S, Strizki J, Barnard RJ et al.. (2014)
Combination of vaniprevir with peginterferon and ribavirin significantly increases the rate of SVR in treatment-experienced patients with chronic HCV genotype 1 infection and cirrhosis.
Clin Gastroenterol Hepatol, 12 (6): 1029-37.e5. [PMID:24120953]