Faldaprevir

Faldaprevir
Clinical data
Other names	BI 201335
Routes of; administration	By mouth
ATC code	J05AP04 (WHO) ;
Legal status
Legal status	Abandoned;
Identifiers
	IUPAC name N-[(Cyclopentyloxy)carbonyl]-3-methyl-L-valyl-(4R)-4-({8-bromo-2-[2-(isobutyrylamino)-1,3-thiazol-4-yl]-7-methoxy-4-quinolinyl}oxy)-N-[(1R,2S)-1-carboxy-2-vinylcyclopropyl]-L-prolinamide;
CAS Number	801283-95-4;
PubChem CID	42601552;
DrugBank	DB11808;
ChemSpider	26327117;
UNII	958X4J301A;
ChEMBL	ChEMBL1241348;
Chemical and physical data
Formula	C40H49BrN6O9S
Molar mass	869.82 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)C(=O)Nc1nc(cs1)c2cc(c3ccc(c(c3n2)Br)OC)O[C@@H]4C[C@H](N(C4)C(=O)[C@H](C(C)(C)C)NC(=O)OC5CCCC5)C(=O)N[C@@]6(C[C@H]6C=C)C(=O)O;
	InChI InChI=1S/C40H49BrN6O9S/c1-8-21-17-40(21,36(51)52)46-34(49)27-15-23(18-47(27)35(50)32(39(4,5)6)44-38(53)56-22-11-9-10-12-22)55-29-16-25(26-19-57-37(43-26)45-33(48)20(2)3)42-31-24(29)13-14-28(54-7)30(31)41/h8,13-14,16,19-23,27,32H,1,9-12,15,17-18H2,2-7H3,(H,44,53)(H,46,49)(H,51,52)(H,43,45,48)/t21-,23-,27+,32-,40-/m1/s1; Key:LLGDPTDZOVKFDU-XUHJSTDZSA-N;

Faldaprevir was an experimental drug for the treatment of hepatitis C (HCV). It was being developed by Boehringer-Ingelheim and reached Phase III clinical trials in 2011.[1] Boehringer announced in 2014 that it would not pursue approval of the drug any more because of better HCV treatments having become available.[2]

Mechanism of action

Faldaprevir is a hepatitis C virus protease inhibitor.

Studies

Faldaprevir was tested in combination regimens with pegylated interferon and ribavirin, and in interferon-free regimens with other direct-acting antiviral agents including deleobuvir.

Data from the SOUND-C2 study, presented at the 2012 AASLD Liver Meeting, showed that a triple combination of faldaprevir, deleobuvir, and ribavirin performed well in HCV genotype 1b patients.[3] Efficacy fell below 50%, however, for dual regimens without ribavirin and for genotype 1a patients.

References

Clinical trial number NCT01343888 for "Efficacy and Safety of BI 201335 (Faldaprevir) in Combination With Pegylated Interferon-alpha and Ribavirin in Treatment-naïve Genotype 1 Hepatitis C Infected Patients (STARTverso 1)" at ClinicalTrials.gov
"Hepatitis C: Aus für Boehringers Faldaprevir". www.pharmazeutische-zeitung.de.
Interferon-free hepatitis C treatment with faldaprevir proves safe and effective in people with cirrhosis. Alcorn, K. Aidsmap.com. 20 November 2012.

External links

Faldaprevir at chem.sis.nlm.nih.gov
Faldaprevir at chemicalregister.com

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[1] Clinical trial number NCT01343888 for "Efficacy and Safety of BI 201335 (Faldaprevir) in Combination With Pegylated Interferon-alpha and Ribavirin in Treatment-naïve Genotype 1 Hepatitis C Infected Patients (STARTverso 1)" at ClinicalTrials.gov

[2] "Hepatitis C: Aus für Boehringers Faldaprevir". www.pharmazeutische-zeitung.de.

[3] Interferon-free hepatitis C treatment with faldaprevir proves safe and effective in people with cirrhosis. Alcorn, K. Aidsmap.com. 20 November 2012.