What is the Cyclopenta(c)pyrrole-1-carboxamide, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydro-, (1S,3aR,6aS)-?

Cyclopenta(c)pyrrole-1-carboxamide, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydro-, (1S,3aR,6aS)- is White powder, while it's Molecular Formula is C36H53N7O6. White powder A labelled peptidomimetic inhibitor of hepatitis C virus protease.

What is the CAS number for Cyclopenta(c)pyrrole-1-carboxamide, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydro-, (1S,3aR,6aS)-?

The CAS number of Cyclopenta(c)pyrrole-1-carboxamide, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydro-, (1S,3aR,6aS)- is 402957-28-2.

What is Cyclopenta(c)pyrrole-1-carboxamide, (2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydro-, (1S,3aR,6aS)- (402957-28-2) used for?

The hepatitis C virus (HCV) protease inhibitor telaprevir (VX-950, MP-424,LY-570310) was approved by the U.S. FDA in May 2011 for the treatmentof genotype 1 chronic HCV infection in adult patients in combination withpeginterferon alfa and ribavirin (PR). Telaprevir and boceprevir (videsupra) are the first two HCV protease inhibitors to be approved fortreatment of HCV infection. Telaprevir is a HCV NS3-4A proteaseinhibitor that exerts its antiviral effect by blocking the release ofnonstructural viral proteins from a polyprotein precursor. Telaprevir is apotent inhibitor of the protease (IC50=10 nM) and is active in cell culture(HCV 1b replicon assay, EC50=354 nM). Telaprevir was identified fromefforts to truncate a decamer peptide inhibitor derived from the naturalsubstrate NS5A-5B and was guided by structure-based design. The ketoamidegroup of telaprevir forms a covalent, reversible bond with the activesite serine hydroxyl of the protease and compensates for the loss of affinityresulting from truncation of the peptide. Despite the presence of the reactive keto-amide group, telaprevir is >500-fold less potent against other serineproteases. Synthesis of the key octahydrocyclopenta[c]pyrrole-1-carboxylicacid fragment of telaprevir is achieved by a-deprotonation of Boc-protected3-azabicyclo[3.3.0]nonane followed by reaction with CO2 and resolution ofthe racemic acid. Alternatively, deprotonation is carried out in thepresence of a chiral amine to give the enantiomerically enriched acid.InChI:InChI=1/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25?,27-,28-,30+/m0/s1

Product classification

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Telaprevir

Product Name: Telaprevir
CasNo: 402957-28-2
Purity:
Appearance: White powder

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CasNo： 402957-28-2

Molecular Formula： C₃₆H₅₃N₇O₆

Appearance： White powder

Cosmetics Grade Telaprevir 402957-28-2 For Sale with Good Price

Molecular Formula:C36H53N7O6
Molecular Weight:679.86
Appearance/Colour:White powder
PKA:11.84±0.20(Predicted)
PSA：179.56000
Density:1.25 g/cm³
LogP:3.94740

Telaprevir(Cas 402957-28-2) Usage

Description	Telaprevir is a drug developed by Vertex Pharmaceuticals and Johnson & Johnson under the brand names Incivek and Incivo for the treatment of hepatitis C. It is a member of a class of antiviral drugs called protease inhibitors.
Uses	Telaprevir works by decreasing the amount of hepatitis C virus (HCV) in the body. Telaprevir may not prevent the spread of hepatitis C to other people. Telaprevir is a NS3/4a protease inhibitor used to inhibit viral HCV replication. NS3/4a protease is an integral part of viral replication and mediates the cleavage the virally encoded polyprotein to mature proteins (NS4A, NS4B, NS5A and NS5B) Label. Telaprevir inhibits NS3/4A with an IC50 of 10nM.
Metabolism	Extensively metabolised in the liver, involving hydrolysis, oxidation, and reduction. Multiple metabolites were detected in faeces, plasma and urine.
Definition	ChEBI: An oligopeptide consisting of N-(pyrazin-2-ylcarbonyl)cyclohexylalanyl, 3-methylvalyl, octahydrocyclopenta[c]pyrrole-1-carboxy, and 3-amino-N-cyclopropyl-2-oxohexanamide residues joined in sequence. Used f r treatment of chronic hepatitis C virus genotype 1 infection.
Brand name	Incivek

InChI:InChI=1/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25?,27-,28-,30+/m0/s1

402957-28-2 Relevant articles

Review of Boceprevir and Telaprevir for the Treatment of Chronic Hepatitis C

Kyle J Wilby, Nilufar Partovi, Jo-Ann E Ford, Erica D Greanya, Eric M Yoshida

, Canadian Journal of Gastroenterology and Hepatology, 2012

The studies identified assessed boceprevir and telaprevir in genotype-1 hepatitis C patients. In both treatment-naive and treatment-experienced patients, sustained virological response rates were achieved more often with boceprevir or telaprevir in combination with pegylated interferon and ribavirin compared with pegylated interferon and ribavirin alone. Both medications were well tolerated, with anemia presenting as the most treatment-limiting adverse effect.

Telaprevir with Peginterferon and Ribavirin for Chronic HCV Genotype 1 Infection

John G. McHutchison, M.D., Gregory T. Everson, M.D., Stuart C. Gordon, M.D., Ira M. Jacobson, M.D., Mark Sulkowski, M.D., Robert Kauffman, M.D., Lindsay McNair, M.D., John Alam, M.D., and Andrew J. Muir, M.D., for the PROVE1 Study Team*

, N Engl J Med 2009;360:1827-1838

Viral breakthrough occurred in 7% of patients receiving telaprevir. The rate of discontinuation because of adverse events was higher in the three telaprevir-based groups (21%, vs. 11% in the PR48 group), with rash the most common reason for discontinuation. Treatment with a telaprevir-based regimen significantly improved sustained virologic response rates in patients with genotype 1 HCV, albeit with higher rates of discontinuation because of adverse events.

Response-Guided Telaprevir Combination Treatment for Hepatitis C Virus Infection

Kenneth E. Sherman, M.D., Ph.D., Steven L. Flamm, M.D., Nezam H. Afdhal, M.D., David R. Nelson, M.D., Mark S. Sulkowski, M.D., Gregory T. Everson, M.D., Michael W. Fried, M.D.

, N Engl J Med 2011;365:1014-1024

We enrolled patients with chronic infection with HCV genotype 1 who had not previously received treatment. All patients received telaprevir at a dose of 750 mg every 8 hours, peginterferon alfa-2a at a dose of 180 μg per week, and ribavirin at a dose of 1000 to 1200 mg per day, for 12 weeks (T12PR12), followed by peginterferon–ribavirin.

402957-28-2 Process route

: 1257874-86-4
C₃₈H₅₇N₇O₇

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide

Conditions

Conditions	Yield
C₃₈H₅₇N₇O₇; With methanol; potassium carbonate; at 20 ℃; for 0.5h; With Dess-Martin periodane; In dichloromethane; at 20 ℃;	80%
C₃₈H₅₇N₇O₇; With potassium carbonate; In methanol; With Dess-Martin periodane; In dichloromethane;	80%

: 402959-36-8
(1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-[(2-pyrazinylcarbonyl)amino] acetyl]amino]-3,3-dimethylbutanoyl]-N-[(1S)-1-[(cyclopropylamino)(hydroxy)acetyl]butyl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxamide

: 402957-28-2
(1S,3aR,6aS)-2-((S)-2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-3,3-dimethylbutanoyl)-N-((S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl)octahydrocyclopenta[c]pyrrole-1-carboxamide