telaprevir

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

Chemical data

Formula

C36H53N7O6

Molecular weight

679.8 g/mol

IUPAC name

(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

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

InChIKey

BBAWEDCPNXPBQM-GDEBMMAJSA-N

XLogP

4.2

Polar surface area

180 Ų

H-bond donors

4

H-bond acceptors

8

Formal charge

0

via PubChem

Drug data · ChEMBL

Max clinical phase

Approved

Molecule type

Small molecule

First approval

2011

Admin. routes

oral

Indications

liver disease, hepatitis C virus infection, chronic hepatitis C virus infection, Thrombocytopenia

via ChEMBL · EBI

• 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

Has use

medication

via Wikidata · CC0