telaprevir

Also known as VX-950, VX 950, (1S,3aR,6aS)-(2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydrocyclopenta(c)pyrrole-1-carboxamide, (1S,3AR,6as)-(2S)-2-cyclohexyl-N-(pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-((1S)-1-((cyclopropylamino)oxoacetyl)butyl)octahydrocyclopenta(c)pyrrole-1-carboxamide

Telaprevir (VX-950), was marketed under the brand names Incivek and Incivo, is a pharmaceutical drug for the treatment of hepatitis C co-developed by Vertex Pharmaceuticals and Johnson & Johnson. It is a member of a class of antiviral drugs known as protease inhibitors. Specifically, telaprevir inhibits the hepatitis C viral enzyme NS3/4A serine protease. Telaprevir is only indicated for use against hepatitis C genotype 1 viral infections and has not been proven to be safe or effective when used for other genotypes of the virus. The standard therapy of pegylated interferon and ribavirin is les

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 458630745
Drug.IUPAC_name: (1S,3aR,6aS)-2-[(2S)-2-[[(2S)-2-Cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-1-carboxamide | image = Telaprevir structure.svg | image_class = skin-invert-image | width = 280 | tradename = Incivek, Incivo | Drugs.com = | MedlinePlus = a611038 | licence_US = Telaprevir | pregnancy_AU = | pregnancy_US = B | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = Rx-only | legal_status = | routes_of_administration = Oral | bioavailability = | protein_bound = 59–76% | metabolism = extensive hepatic | elimination_half-life = 9–11 hours | excretion = 90% (bile), 9% (exhaled air), 1% (urine) | IUPHAR_ligand = 7871 | CAS_number_Ref = | CAS_number = 402957-28-2 | ATC_prefix = J05 | ATC_suffix = AP02 | ChEBI_Ref = | ChEBI = 68595 | ChEMBL_Ref = | ChEMBL = 231813 | PubChem = 3010818 | DrugBank_Ref = | DrugBank = DB05521 | ChemSpiderID_Ref = | ChemSpiderID = 2279948 | UNII_Ref = | UNII = 655M5O3W0U | KEGG_Ref = | KEGG = D09012 | NIAID_ChemDB = 213006 | C=36 | H=53 | N=7 | O=6 | StdInChI_Ref = | StdInChI = 1S/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 | StdInChIKey_Ref = | StdInChIKey = BBAWEDCPNXPBQM-GDEBMMAJSA-N | SMILES = CCC[C@@H](C(=O)C(=O)NC1CC1)NC(=O)[C@@H]2[C@H]3CCC[C@H]3CN2C(=O)[C@H](C(C)(C)C)NC(=O)[C@H](C4CCCCC4)NC(=O)c5cnccn5 | SMILES2 = C0CC0NC(=O)C(=O)[C@H](CCC)NC(=O)[C@@H]1[C@H]2CCC[C@H]2CN1C(=O)[C@H](C(C)(C)C)NC(=O)[C@H](C3CCCCC3)NC(=O)c4nccnc4

via Wikipedia infobox

Research

1,588 papers

Telaprevir.Drugs in R&D · 2010
Telaprevir user's guide.Clinics in liver disease · 2011
[Telaprevir resistance].Enfermedades infecciosas y microbiologia clinica · 2013
Telaprevir user's guide.Liver international : official journal of the International Association for the Study of the Liver · 2012
Telaprevir-related dermatitis.JAMA dermatology · 2013

via PubMed

Wikidata facts

Mass: 679.405732

Show 5 more facts

chemical formula: C₃₆H₅₃N₇O₆
isomeric SMILES: CCC[C@@H](C(=O)C(=O)NC1CC1)NC(=O)[C@@H]2[C@H]3CCC[C@H]3CN2C(=O)[C@H](C(C)(C)C)NC(=O)[C@H](C4CCCCC4)NC(=O)C5=NC=CN=C5
canonical SMILES: CCCC(C(=O)C(=O)NC1CC1)NC(=O)C2C3CCCC3CN2C(=O)C(C(C)(C)C)NC(=O)C(C4CCCCC4)NC(=O)C5=NC=CN=C5
Commons category: Telaprevir
defined daily dose: 2.25

Sources (6)

via Wikidata · CC0

~6 min read

Article

5 sections

Contents

Clinical trials and approvals
Adverse effects
Availability
Research
References

==Clinical trials and approvals== In a randomized controlled trial (PROVE3) of patients in whom standard treatment with peginterferon alfa-2a and ribavirin had failed, repeat treatment with the addition of telaprevir was more likely to have a sustained virological response (SVR) than repeat treatment with peginterferon alfa-2a and ribavirin alone. In patients who received peginterferon alfa-2a and ribavirin for a year, the addition of telaprevir for 24 weeks achieved an SVR of 53% compared to 14% in patients who did not receive telaprevir. In that study, shorted treatment with only three months of telaprevir and six months of treatment peginterferon alfa-2a and ribavirin achieved an SVR of 51%. In a second randomized controlled trial (REALIZE) of patients who had previously relapsed or had only a partial response, rates of SVR were higher in patients treated with telaprevir (83% to 88%) compared to 24% in controls. In a third trial (ADVANCE) for previously untreated patients, patients taking telaprevir had a SVR (69% to 75%) versus 44% in the control group.