Telaprevir

Overview

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 less effective than telaprevir in those with genotype 1.[1][2] WP

Risks and side effects

Adverse effects

The most common adverse effect is rash. Grade 3 adverse events (mainly anemia and leukopenia/neutropenia) were more frequent in the telaprevir groups than in the control group (37% vs. 22%). After receiving reports of serious skin reactions, some fatal, in patients taking the hepatitis C drug Incivek (telaprevir) in combination with drugs peginterferon alfa and ribavirin (Incivek combination treatment), the US Food and Drug Administration (FDA) has added a black box warning to the label of this Vertex product. On December 19, 2012, Vertex announced it would add a boxed warning of possible side effects on the US labels of telaprevir, following "reports of a small number of fatal skin reactions in patients who continued to receive Incivek combination therapy after a serious skin reaction was identified." The FDA reported two people had died from serious skin reactions caused by the Incivek combination treatment and a total of 112 patients had developed serious skin reactions of two different types.[3] WP

Research

Research

Studies in mice have indicated that telaprevir may also show activity against enterovirus D68, which has been implicated as a causative agent for acute flaccid myelitis. Since telaprevir is already approved for use in humans in the treatment of hepatitis C, it is now being researched to see whether it could be useful for the treatment of AFM in humans.[4][5] WP

Chemistry

Formula

C36H53N7O6 PC

CAS number

402957-28-2 PC

Molar mass (g/mol)

679.8 PC

IUPAC name (computed by PubChem)

(3S,3aS,6aR)-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-3-carboxamide PC

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 PC

InChIKey

BBAWEDCPNXPBQM-GDEBMMAJSA-N PC

PubChem CID

3010818

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Revill P, Serradell N, Bolos J, Rosa E. Telaprevir. Drugs of the Future. 2007. doi:10.1358/dof.2007.032.09.1138229
2. Journal / agency Lin C, Kwong AD, Perni RB. Discovery and development of VX-950, a novel, covalent, and reversible inhibitor of hepatitis C virus NS3.4A serine protease. Infectious Disorders Drug Targets. March 2006. doi:10.2174/187152606776056706 · PMID 16787300
3. Other Staff, Boston.com. December 19, 2012. Vertex updates label of hepatitis C drug after reports of a 'small number of fatal skin reactions
4. Journal / agency Musharrafieh R. Validating Enterovirus D68-2Apro as an Antiviral Drug Target and the Discovery of Telaprevir as a Potent D68-2Apro Inhibitor. Journal of Virology. 2019. doi:10.1128/jvi.02221-18 · PMID 30674624 · PMC6430540
5. Journal / agency Frost J, Rudy MJ, Leser JS, Tan H, Hu Y, Wang J, Clarke P, Tyler KL. Telaprevir Treatment Reduces Paralysis in a Mouse Model of Enterovirus D68 Acute Flaccid Myelitis. J Virol. May 2023. doi:10.1128/jvi.00156-23 · PMID 37154751 · PMC10231134

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.