Boceprevir

Boceprevir
Clinical data
Trade namesVictrelis
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa611039
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding75%[1]
Elimination half-life3.4 hours[1]
Identifiers
  • (1R,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2(S)-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.226.246 Edit this at Wikidata
Chemical and physical data
FormulaC27H45N5O5
Molar mass519.687 g·mol−1
3D model (JSmol)
  • O=C(N3[C@H](C(=O)NC(C(=O)C(=O)N)CC1CCC1)[C@H]2C(C)([C@H]2C3)C)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C
  • InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1 checkY
  • Key:LHHCSNFAOIFYRV-DOVBMPENSA-N checkY

Boceprevir (INN, trade name Victrelis) is a protease inhibitor used to treat hepatitis caused by hepatitis C virus (HCV) genotype 1.[2][3] It binds to the HCV nonstructural protein 3 active site.[4]

It was initially developed by Schering-Plough,[5] then by Merck after it acquired Schering in 2009. It was approved by the FDA in May 2011.[6] In January 2015, Merck announced that they would be voluntarily withdrawing Victrelis from the market due to the overwhelming superiority of newer direct-acting antiviral agents, such as ledipasvir/sofosbuvir.[7]

  1. ^ 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.
  2. ^ Degertekin B, Lok AS (May 2008). "Update on viral hepatitis: 2007". Current Opinion in Gastroenterology. 24 (3): 306–311. doi:10.1097/MOG.0b013e3282f70285. PMID 18408458. S2CID 43762307.
  3. ^ Njoroge FG, Chen KX, Shih NY, Piwinski JJ (January 2008). "Challenges in modern drug discovery: a case study of boceprevir, an HCV protease inhibitor for the treatment of hepatitis C virus infection". Accounts of Chemical Research. 41 (1): 50–59. doi:10.1021/ar700109k. PMID 18193821. S2CID 2629035.
  4. ^ "Boceprevir - FDA Antiviral Drugs" (PDF). FDA. April 2011. Retrieved 1 April 2014.
  5. ^ "Interim Results from Boceprevir Phase II Study in Genotype 1 Treatment-Naive Hepatitis C Patients Presented At EASL - Forbes.com". Forbes.com (Press release). Archived from the original on 2011-05-15. Retrieved 2008-05-19.
  6. ^ "FDA Approves Merck's VICTRELIS™ (boceprevir), First-in-Class Oral Hepatitis C Virus (HCV) Protease Inhibitor" (Press release). Merck & Co. Archived from the original on 2011-05-15. Retrieved 2011-05-14.
  7. ^ Paul J Bader, RPh (January 2015). "Merck Voluntarily Discontinuing VICTRELIS® (boceprevir) 200 mg Capsules" (PDF). Letter to. Merck & Co., Inc. Retrieved 2016-05-08.