CILUPREVIR

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17155849 | https://www.clinicaltrials.gov/ct2/show/NCT02226939

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
Hepatitis C virus NS3 protease/helicase 5 Target ID: CHEMBL4893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17002221	Inhibitor 8297		3.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 42 Sources: https://www.clinicaltrials.gov/ct2/show/NCT02226939	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

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

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	3548AH	https://aksci.com/item_detail.php?cat=3548AH
AstaTech	43144	http://astatechinc.com/CPSResult.php?CRNO=43144
Molnova	M13936	https://www.molnova.com/en/serch-list.html?keywords=M13936
MuseChem	I006005	https://www.musechem.com/product/I006005.html
eMolecules	176929104	https://orderbb.emolecules.com/search/#?query=176929104

PubMed

Title	Date	PubMed
Potent inhibitors of the hepatitis C virus NS3 protease: use of a novel P2 cyclopentane-derived template.	2006 Aug 1	16675222
Ultra-rapid cardiotoxicity of the hepatitis C virus protease inhibitor BILN 2061 in the urokinase-type plasminogen activator mouse.	2007 Oct	17919490
MK-7009, a potent and selective inhibitor of hepatitis C virus NS3/4A protease.	2010 Jan	19841155
Discovery of novel urea-based hepatitis C protease inhibitors with high potency against protease-inhibitor-resistant mutants.	2012 Apr 12	22471376
In vitro efficacy of approved and experimental antivirals against novel genotype 3 hepatitis C virus subgenomic replicons.	2013 Nov	24013001
Inhibition of hepatitis C virus replication by GS-6620, a potent C-nucleoside monophosphate prodrug.	2014	24419349
Preclinical characterization of the novel hepatitis C virus NS3 protease inhibitor GS-9451.	2014	23939899

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:04:41 GMT 2023` Edited by `admin` on `Fri Dec 15 16:04:41 GMT 2023`
Record UNII	75C8DU40T0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CILUPREVIR

Official Name

English

(2R,6S,12Z,13aS,14aR,16aS)-6-[[(Cyclopentyloxy)carbonyl]amino]-2-[[7-methoxy-2-[2-[(1-methylethyl)amino]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-14

Systematic Name

English

BILN 2061 ZW

Code

English

CILUPREVIR [USAN]

Common Name

English

BILN-2061-ZW

Code

English

BILN-2061

Code

English

ciluprevir [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281