Ciluprevir

Ciluprevir
Clinical data

Routes of administration	By mouth
ATC code	None
Legal status
Legal status	Development terminated
Pharmacokinetic data
Protein binding	>99.1%^[1]
Identifiers
IUPAC name (2R,6S,12Z,13aS,14aR,16aS)-6-[(Cyclopentyloxycarbonyl)amino]-2-({7-methoxy-2-[(propan-2-ylamino)-1,3-thiazol-4-yl]quinolin- 4-yl}oxy)-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a] [1,4]diazacyclopentadecine-14a(5H)-carboxylic acid
CAS Number	300832-84-2
PubChem CID	9853710
ChemSpider	8029420
UNII	75C8DU40T0
ChEMBL	ChEMBL297884
CompTox Dashboard (EPA)	DTXSID50870316
Chemical and physical data
Formula	C₄₀H₅₀N₆O₈S
Molar mass	774.93 g·mol⁻¹
3D model (JSmol)
SMILES O=C2N[C@]7(C(=O)O)C[C@H]7/C=C\CCCCC[C@H](NC(=O)OC1CCCC1)C(=O)N6[C@H]2C[C@@H](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.^[2] Ciluprevir is a potent competitive reversible inhibitor of NS3/4A protease from HCV genotype 1a (K_i = 0.3 nM) and 1b (K_i = 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

^ ^a ^b 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.
^ 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.
^ 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)	Asunaprevir Boceprevir^‡ Ciluprevir^§ Danoprevir^† Faldaprevir^‡ Glecaprevir Grazoprevir Narlaprevir Paritaprevir Simeprevir Sovaprevir^† Telaprevir^‡ Vaniprevir Vedroprevir^§ Voxilaprevir
NS5A inhibitors (–asvir)	Coblopasvir Daclatasvir^# Elbasvir Ledipasvir Odalasvir^† Ombitasvir Pibrentasvir Ravidasvir^† Ruzasvir^† Samatasvir^† Velpatasvir
NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Bemnifosbuvir^† Dasabuvir^# Deleobuvir^§ Filibuvir^§ GS-6620^§ IDX-184^§ Setrobuvir^§ Sofosbuvir^# Tegobuvir^§ TMC-647055^§ Radalbuvir^† Uprifosbuvir^†
Combination drugs	Elbasvir/grazoprevir Glecaprevir/pibrentasvir Ledipasvir/sofosbuvir^# Ombitasvir/paritaprevir/ritonavir^# Sofosbuvir/daclatasvir Sofosbuvir/velpatasvir^# Sofosbuvir/velpatasvir/voxilaprevir

Hepatitis D

Bulevirtide

Picornavirus

viral entry: Pleconaril^†

Anti-influenza agents

neuraminidase inhibitors/release phase (Oseltamivir^#
Zanamivir
Peramivir, Laninamivir^†)

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^# Peginterferon alfa-2b^#
3CL protease inhibitors (–trelvir)	Ensitrelvir^† Ibuzatrelvir Lufotrelvir Nirmatrelvir^† (+ritonavir)^† Rupintrivir Simnotrelvir (+ritonavir^†)
RNA pol inhibitors	CMX521^§ Deuremidevir^† Favipiravir Galidesivir^† GS-441524^§ Remdesivir MK-608^§ Mericitabine^† Molnupiravir NITD008^§ Ribavirin^# Taribavirin^† Triazavirin Valopicitabine^†
Multiple/Unknown/Other	EICAR^§ Merimepodib^§ Moroxydine Presatovir^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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