VANIPREVIR

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 Search

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://adisinsight.springer.com/drugs/800025599
Curator's Comment: Description was created based on several sources, including http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=35797 | https://www.ncbi.nlm.nih.gov/pubmed/19841155

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 Target	Pharmacology	Condition	Potency
Hepatitis C virus serine protease, NS3/NS4A 13 Target ID: CHEMBL2095231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19841155	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 42 Sources: http://adisinsight.springer.com/drugs/800025599	Primary		Approved 8429	VANIHEP Approved Use VANIHEP Capsules 150mg (Vaniprevir) indicated for the improvement of viremia in the following patients with serogroup 1 (genotype I [1a] or II [1b]) chronic hepatitis C: Patients with high levels of blood HCV RNA who are treatment-naive, or Patients who are non-responders or relapsed to therapy including interferon Launch Date 1.41160323E12

PubMed

Title	Date	PubMed
MK-7009, a potent and selective inhibitor of hepatitis C virus NS3/4A protease.	2010 Jan	19841155
Discovery of vaniprevir (MK-7009), a macrocyclic hepatitis C virus NS3/4a protease inhibitor.	2010 Mar 25	20163176
Synthesis of vaniprevir (MK-7009): lactamization to prepare a 20-membered [corrected] macrocycle.	2011 Oct 7	21838271
Synthesis of the HCV protease inhibitor Vaniprevir (MK-7009) using ring-closing metathesis strategy.	2012 Apr 20	22458448
Vaniprevir with pegylated interferon alpha-2a and ribavirin in treatment-naïve patients with chronic hepatitis C: a randomized phase II study.	2012 Sep	22473713
A phase 2B study of MK-7009 (vaniprevir) in patients with genotype 1 HCV infection who have failed previous pegylated interferon and ribavirin treatment.	2013 Jul	23439259
Characterization of vaniprevir, a hepatitis C virus NS3/4A protease inhibitor, in patients with HCV genotype 1 infection: safety, antiviral activity, resistance, and pharmacokinetics.	2013 Sep	23747481

Patents

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 Created by `admin` on `Fri Dec 15 16:01:19 UTC 2023` Edited by `admin` on `Fri Dec 15 16:01:19 UTC 2023`
Record UNII	CV3X74AO1H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VANIPREVIR

Official Name

English

MK7009

Code

English

Vaniprevir [WHO-DD]

Common Name

English

CYCLOPROPANECARBOXAMIDE, N-(((6-(2-CARBOXY-2,3-DIHYDRO-1H-ISOINDOL-4-YL)-2,2-DIMETHYLHEXYL)OXY)CARBONYL)-3-METHYL-L-VALYL-(4R)-4-HYDROXY-L-PROLYL-1-AMINO-N-(CYCLOPROPYLSULFONYL)-2-ETHYL-, (1->2)-LACTONE, (1R,2R)-

Common Name

English

VANIPREVIR [JAN]

Common Name

English

VANIPREVIR [MI]

Common Name

English

MK-7009

Code

English

vaniprevir [INN]

Common Name

English

VANIPREVIR [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C783