Boceprevir

Boceprevir
Clinical data
Trade names	Victrelis
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a611039
License data	EU EMA: by INN; US FDA: Boceprevir;
Routes of; administration	Oral
ATC code	J05AP03 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Protein binding	75%
Elimination half-life	3.4 hours
Identifiers
	IUPAC name (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	394730-60-0 ;
PubChem CID	10324367;
IUPHAR/BPS	7876;
DrugBank	DB08873 ;
ChemSpider	8499830 ;
UNII	89BT58KELH;
KEGG	D08876 ;
ChEMBL	ChEMBL218394 ;
NIAID ChemDB	398493;
CompTox Dashboard (EPA)	DTXSID30960103 ;
ECHA InfoCard	100.226.246
Chemical and physical data
Formula	C27H45N5O5
Molar mass	519.687 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:LHHCSNFAOIFYRV-DOVBMPENSA-N ;

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]

^ ^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.
^ 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.
^ 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.
^ "Boceprevir - FDA Antiviral Drugs" (PDF). FDA. April 2011. Archived from the original (PDF) on May 23, 2011. Retrieved 1 April 2014.
^ "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.
^ "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.
^ Paul J Bader, RPh (January 2015). "Merck Voluntarily Discontinuing VICTRELIS® (boceprevir) 200 mg Capsules" (PDF). Letter to. Merck & Co., Inc. Archived from the original (PDF) on May 1, 2015. Retrieved 2016-05-08.

[PMC3345276-1] 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.

[pmid18408458-2] 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.

[pmid18193821-3] 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. Archived from the original (PDF) on May 23, 2011. Retrieved 1 April 2014.

[PhaseII-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.

[Victrelis®_Market_Withdraw-7] Paul J Bader, RPh (January 2015). "Merck Voluntarily Discontinuing VICTRELIS® (boceprevir) 200 mg Capsules" (PDF). Letter to. Merck & Co., Inc. Archived from the original (PDF) on May 1, 2015. Retrieved 2016-05-08.

[1]

[2]

[3]

[4]

[5]

[6]

[7]