Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C40H50N6O8S |
Molecular Weight | 774.925 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@]1(NC(=O)[C@]3([H])C[C@H](CN3C(=O)[C@H](CCCCCC=C2)NC(=O)OC4CCCC4)OC5=CC(=NC6=C5C=CC(OC)=C6)C7=CSC(NC(C)C)=N7)C(O)=O
InChI
InChIKey=PJZPDFUUXKKDNB-KNINVFKUSA-N
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
Molecular Formula | C40H50N6O8S |
Molecular Weight | 774.925 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Ciluprevir (BILN-2061) is a selective inhibitor of the HCV NS3 serine protease, which was developed by Boehringer Ingelheim for the treatment of hepatitis C infection. The drug was discontinued in phase II due to adverse events such as cardiac toxicity (demonstrated in animals). In the cell-based replicon assay, ciluprevir inhibited HCV RNA replication at low nanomolar levels. It had inhibitory rate constant (Ki) values of 0.3 and 0.66 nM for the NS3 proteases of HCV genotypes 1a and -1b, respectively.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17002221 |
3.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2799.99 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15732092 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CILUPREVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1189.16 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15732092 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CILUPREVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13318.27 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15732092 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CILUPREVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5323.08 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15732092 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
CILUPREVIR plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
An NS3 protease inhibitor with antiviral effects in humans infected with hepatitis C virus. | 2003 Nov 13 |
|
In vitro resistance studies of hepatitis C virus serine protease inhibitors, VX-950 and BILN 2061: structural analysis indicates different resistance mechanisms. | 2004 Apr 23 |
|
Structure-activity study on a novel series of macrocyclic inhibitors of the hepatitis C virus NS3 protease leading to the discovery of BILN 2061. | 2004 Mar 25 |
|
Potent inhibitors of the hepatitis C virus NS3 protease: use of a novel P2 cyclopentane-derived template. | 2006 Aug 1 |
|
Ultra-rapid cardiotoxicity of the hepatitis C virus protease inhibitor BILN 2061 in the urokinase-type plasminogen activator mouse. | 2007 Oct |
|
Preclinical characteristics of the hepatitis C virus NS3/4A protease inhibitor ITMN-191 (R7227). | 2008 Dec |
|
Synergy of a hepatitis C virus (HCV) NS4A antagonist in combination with HCV protease and polymerase inhibitors. | 2008 May |
|
Substituted imidazopyridines as potent inhibitors of HCV replication. | 2009 May |
|
Improved P2 phenylglycine-based hepatitis C virus NS3 protease inhibitors with alkenylic prime-side substituents. | 2010 Jul 15 |
|
Discovery of a potent and selective noncovalent linear inhibitor of the hepatitis C virus NS3 protease (BI 201335). | 2010 Sep 9 |
|
A twenty-eight-day mechanistic time course study in the rhesus monkey with hepatitis C virus protease inhibitor BILN 2061. | 2011 Apr |
|
Novel, potent, and orally bioavailable phosphinic acid inhibitors of the hepatitis C virus NS3 protease. | 2011 Jun 15 |
|
Estimation of inhibitory quotient using a comparative equilibrium dialysis assay for prediction of viral response to hepatitis C virus inhibitors. | 2011 May |
|
Discovery of novel urea-based hepatitis C protease inhibitors with high potency against protease-inhibitor-resistant mutants. | 2012 Apr 12 |
|
Inhibitory effects of polyphenols toward HCV from the mangrove plant Excoecaria agallocha L. | 2012 Jan 15 |
|
In vitro efficacy of approved and experimental antivirals against novel genotype 3 hepatitis C virus subgenomic replicons. | 2013 Nov |
|
Inhibition of hepatitis C virus replication by GS-6620, a potent C-nucleoside monophosphate prodrug. | 2014 |
|
Preclinical characterization of the novel hepatitis C virus NS3 protease inhibitor GS-9451. | 2014 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.clinicaltrials.gov/ct2/show/NCT02226939
In a clinical trial, cipuprevir was given at a dose of 200 mg p.o. at two consecutive days, two times daily.
Route of Administration:
Oral
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 16:04:41 UTC 2023
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Fri Dec 15 16:04:41 UTC 2023
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Record UNII |
75C8DU40T0
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C281
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NCI_THESAURUS |
C783
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8440
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9853710
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PP-15
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C76016
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CHEMBL297884
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300000034118
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75C8DU40T0
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DTXSID50870316
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DB05868
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300832-84-2
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