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Ciluprevir

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Chemical compound Pharmaceutical compound
Ciluprevir
Clinical data
Routes of
administration		By mouth
ATC code
  • None
Legal status
Legal status
  • Development terminated
Pharmacokinetic data
Protein binding>99.1%
Identifiers
IUPAC name
  • (2R,6S,12Z,13aS,14aR,16aS)-6--2-({7-methoxy-2-quinolin- 4-yl}oxy)-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropapyrrolo diazacyclopentadecine-14a(5H)-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC40H50N6O8S
Molar mass774.93 g·mol
3D model (JSmol)
SMILES
  • O=C2N7(C(=O)O)C7/C=C\CCCCC(NC(=O)OC1CCCC1)C(=O)N62C(Oc3cc(nc4c3ccc(OC)c4)c5nc(sc5)NC(C)C)C6
InChI
  • InChI=1S/C40H50N6O8S/c1-23(2)41-38-43-32(22-55-38)31-19-34(28-16-15-26(52-3)17-30(28)42-31)53-27-18-33-35(47)45-40(37(49)50)20-24(40)11-7-5-4-6-8-14-29(36(48)46(33)21-27)44-39(51)54-25-12-9-10-13-25/h7,11,15-17,19,22-25,27,29,33H,4-6,8-10,12-14,18,20-21H2,1-3H3,(H,41,43)(H,44,51)(H,45,47)(H,49,50)/b11-7-/t24-,27-,29+,33+,40-/m1/s1
  • Key:PJZPDFUUXKKDNB-KNINVFKUSA-N

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. 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).

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.

References

  1. ^ Tan SL, He Y, eds. (2011). Hepatitis C: Antiviral Drug Discovery and Development. Norfolk, UK: Caister Academic Press. p. 199. ISBN 978-1-904455-78-3.
  2. Tan SL (2006). "6. HCV NS3-4A Serine Protease". In Tan SL (ed.). Hepatitis C Viruses: Genomes and Molecular Biology. Norfolk (UK): Horizon Bioscience. ISBN 978-1-904933-20-5. PMID 21250377.
  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 3185733. PMID 21994705.
RNA virus antivirals (primarily J05, also S01AD and D06BB)
Hepatitis C
NS3/4A protease inhibitors (–previr)
NS5A inhibitors (–asvir)
NS5B RNA polymerase inhibitors (–buvir)
Combination drugs
Hepatitis D
Picornavirus
Anti-influenza agents
Multiple/general
Interferon
3CL protease inhibitors (–trelvir)
RNA pol inhibitors
Multiple/Unknown/Other
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