Telaprevir

Telaprevir
Clinical data
Trade names	Incivek, Incivo
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a611038
License data	US FDA: Telaprevir;
Routes of; administration	Oral
ATC code	J05AP02 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Protein binding	59–76%
Metabolism	extensive hepatic
Elimination half-life	9–11 hours
Excretion	90% (bile), 9% (exhaled air), 1% (urine)
Identifiers
	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;
CAS Number	402957-28-2 ;
PubChem CID	3010818;
IUPHAR/BPS	7871;
DrugBank	DB05521 ;
ChemSpider	2279948 ;
UNII	655M5O3W0U;
KEGG	D09012 ;
ChEBI	CHEBI:68595 ;
ChEMBL	ChEMBL231813 ;
NIAID ChemDB	213006;
CompTox Dashboard (EPA)	DTXSID40193304 ;
ECHA InfoCard	100.129.857
Chemical and physical data
Formula	C36H53N7O6
Molar mass	679.863 g·mol−1
3D model (JSmol)	Interactive image; Interactive image;
	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; ; 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;
	InChI InChI=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 ; Key:BBAWEDCPNXPBQM-GDEBMMAJSA-N ;
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Telaprevir (VX-950), 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.^[3] Specifically, telaprevir inhibits the hepatitis C viral enzyme NS3/4A serine protease.^[4] 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.

^ Kim JJ, Culley CM, Mohammad RA (January 2012). "Telaprevir: an oral protease inhibitor for hepatitis C virus infection". American Journal of Health-System Pharmacy. 69 (1): 19–33. doi:10.2146/ajhp110123. PMID 22180548.
^ ^a ^b Kiser JJ, Burton JR, Anderson PL, Everson GT (May 2012). "Review and management of drug interactions with boceprevir and telaprevir". Hepatology. 55 (5): 1620–1628. doi:10.1002/hep.25653. PMC 3345276. PMID 22331658.
^ Revill P, Serradell N, Bolos J, Rosa E (2007). "Telaprevir". Drugs of the Future. 32 (9): 788. doi:10.1358/dof.2007.032.09.1138229.
^ Lin C, Kwong AD, Perni RB (March 2006). "Discovery and development of VX-950, a novel, covalent, and reversible inhibitor of hepatitis C virus NS3.4A serine protease". Infectious Disorders Drug Targets. 6 (1): 3–16. doi:10.2174/187152606776056706. PMID 16787300.

[1] Kim JJ, Culley CM, Mohammad RA (January 2012). "Telaprevir: an oral protease inhibitor for hepatitis C virus infection". American Journal of Health-System Pharmacy. 69 (1): 19–33. doi:10.2146/ajhp110123. PMID 22180548.

[PMC3345276-2] Kiser JJ, Burton JR, Anderson PL, Everson GT (May 2012). "Review and management of drug interactions with boceprevir and telaprevir". Hepatology. 55 (5): 1620–1628. doi:10.1002/hep.25653. PMC 3345276. PMID 22331658.

[3] Revill P, Serradell N, Bolos J, Rosa E (2007). "Telaprevir". Drugs of the Future. 32 (9): 788. doi:10.1358/dof.2007.032.09.1138229.

[pmid16787300-4] Lin C, Kwong AD, Perni RB (March 2006). "Discovery and development of VX-950, a novel, covalent, and reversible inhibitor of hepatitis C virus NS3.4A serine protease". Infectious Disorders Drug Targets. 6 (1): 3–16. doi:10.2174/187152606776056706. PMID 16787300.

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