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
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
DescriptionSources: http://adisinsight.springer.com/drugs/800025599Curator'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
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.
Originator
Sources: http://adisinsight.springer.com/drugs/800025599
Curator's Comment: # Merck & Co
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19841155 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VANIHEP Approved UseVANIHEP 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 Date2014 |
PubMed
Title | Date | PubMed |
---|---|---|
MK-7009, a potent and selective inhibitor of hepatitis C virus NS3/4A protease. | 2010 Jan |
|
Discovery of vaniprevir (MK-7009), a macrocyclic hepatitis C virus NS3/4a protease inhibitor. | 2010 Mar 25 |
|
Synthesis of vaniprevir (MK-7009): lactamization to prepare a 20-membered [corrected] macrocycle. | 2011 Oct 7 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19841155
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).
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NCI_THESAURUS |
C783
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C281
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136047
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DTXSID201029738
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4939
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CHEMBL599872
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DB11929
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VANIPREVIR
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CV3X74AO1H
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SUB35022
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923590-37-8
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m11392
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C152828
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9219
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WW-30
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)