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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H55N5O9S
Molecular Weight 757.936
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VANIPREVIR

SMILES

[H][C@]1(C[C@@H]2CN1C(=O)[C@@H](NC(=O)OCC(C)(C)CCCCC3=C4CN(CC4=CC=C3)C(=O)O2)C(C)(C)C)C(=O)N[C@@]5(C[C@H]5CC)C(=O)NS(=O)(=O)C6CC6

InChI

InChIKey=KUQWGLQLLVFLSM-ONAXAZCASA-N
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

HIDE SMILES / InChI

Molecular Formula C38H55N5O9S
Molecular Weight 757.936
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Vaniprevir (MK-7009) is an non-covalent competitive macrocyclic inhibitor of Hepatitis C virus NS3/4A protease genotype 1a and 1b proteases at subnanomolar concentrations with modestly shifted potency against genotype 2a and 2b proteases at low nanomolar concentrations. Merck & Co. developed vaniprevir in combination with standard therapy for the twice-daily treatment of hepatitis C virus infections. The product has been launched in Japan under name VANIHEP, and Merck reported in its 2014 annual report that the product will only be available in this region.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VANIHEP

PubMed

Sample Use Guides

In Vivo Use Guide
In general, for adults 2 VANIHEP Capsules 150mg (Vaniprevir) (300 mg as the active ingredient) at a time, twice a day for 12 weeks or 24 weeks. This medicine is used in combination with peginterferon α-2b (gene recombination) and ribavirin.
Route of Administration: Oral
In Vitro Use Guide
In a cell-based HCV replicon assay, Vaniprevir (MK-7009) showed potent activity against the genotype 1b enzyme (EC50  5 nM). In a genotype 2a replicon, the potency of MK-7009 was reduced only modestly (EC50  15 nM).
Substance Class Chemical
Record UNII
CV3X74AO1H
Record Status Validated (UNII)
Record Version