Ciluprevir

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Ciluprevir
Ciluprevir.svg
Clinical data
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
  • Development terminated
Pharmacokinetic data
Protein binding >99.1%[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C40H50N6O8S
Molar mass 774.93 g/mol
3D model (JSmol)

Ciluprevir was a drug used experimentally in the treatment of hepatitis C. It is manufactured by Boehringer Ingelheim and developed under the research code of BILN 2061. It was the first-in-class NS3/4A protease inhibitor to enter clinical development and tested in human.[2] Ciluprevir is a potent competitive reversible inhibitor of NS3/4A protease from HCV genotype 1a (Ki = 0.3 nM) and 1b (Ki = 0.66 nM). It shows good selectivity for NS3 protease against representative serine and cysteine proteases, human leukocyte elastase and cathepsin B (IC50 > 30 μM).[1]

Its development was halted in phase Ib clinical trials because of toxicity in animals. However, ciluprevir scaffold was exploited to design new macrocyclic inhibitors such as simeprevir (TMC-435) and danoprevir.[3]

References[edit]

  1. ^ a b Tan, Seng-Lai; He, Yupeng, eds. (2011). Hepatitis C: Antiviral Drug Discovery and Development. Norfolk, UK: Caister Academic Press. p. 199. ISBN 978-1-904455-78-3. 
  2. ^ Tan, Seng-Lai, ed. (2006). "6. HCV NS3-4A Serine Protease". Hepatitis C Viruses: Genomes and Molecular Biology. Norfolk (UK): Horizon Bioscience. ISBN 978-1-904933-20-5. 
  3. ^ Chatel-Chaix, L; Baril, M; Lamarre, D (August 2010). "Hepatitis C Virus NS3/4A Protease Inhibitors: A Light at the End of the Tunnel". Viruses. 2 (8): 1752–65. doi:10.3390/v2081752. PMC 3185733Freely accessible. PMID 21994705.