CAPRAVIRINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H20Cl2N4O2S
Molecular Weight	451.369
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(C)C1=C(SC2=CC(Cl)=CC(Cl)=C2)N(CC3=CC=NC=C3)C(COC(N)=O)=N1

InChI

InChIKey=YQXCVAGCMNFUMQ-UHFFFAOYSA-N

InChI=1S/C20H20Cl2N4O2S/c1-12(2)18-19(29-16-8-14(21)7-15(22)9-16)26(10-13-3-5-24-6-4-13)17(25-18)11-28-20(23)27/h3-9,12H,10-11H2,1-2H3,(H2,23,27)

HIDE SMILES / InChI

Molecular Formula	C20H20Cl2N4O2S
Molecular Weight	451.369
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Capravirine (S-1153, AG1549) is a 1,2,4,5-tetrasubstituted imidazole derivative patented by pharmaceutical company Shionogi as specific inhibitors of HIV-1 reverse transcriptase. However, safety and efficacy studies showed that Capravirine had no specific advantages over currently used NNRTIs. Consequently, clinical trials were discontinued after phase IIb.

Originator

Approval Year

PubMed

Show entries

Title	Date	PubMed
New developments in anti-HIV chemotherapy.	2001 Nov	11562282
Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future.	2004 Jan	17191775
New antiretroviral agents for the treatment of HIV infection.	2004 Jun	16091227
New drugs.	2005 Jul	16011526
A simple sequential incubation method for deconvoluting the complicated sequential metabolism of capravirine in humans.	2005 Oct	16006566

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Patents

Sample Use Guides

In Vivo Use Guide

1400 mg twice daily

Route of Administration: Oral

Substance Class	Chemical
Record UNII	VHC779598X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CAPRAVIRINE

Official Name

English

1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)THIO)-4-(1-METHYLETHYL)-1-(4-PYRIDINYLMETHYL)-, CARBAMATE (ESTER)

Common Name

English

CAPRAVIRINE [USAN]

Common Name

English

capravirine [INN]

Common Name

English

S-1153

Code

English

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Classification Tree

Code System

Code

Reverse Transcriptase Inhibitor

NCI_THESAURUS

C97453

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Code System

Code

Type

Description

EPA CompTox

DTXSID30170689

PRIMARY

PUBCHEM

1783

PRIMARY

MERCK INDEX

m1053

PRIMARY

Merck Index

FDA UNII

VHC779598X

PRIMARY

CAS

178979-85-6

PRIMARY

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Related Record

Type

Details


					859A956UY8

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1

TARGET ORGANISM->INHIBITOR

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR

Amount:


					VHC779598X

CAPRAVIRINE

EXCRETED UNCHANGED

Comments:

Excretion of unchanged capravirine was negligible in urine.

Qualification:

URINE

Amount:


					VHC779598X

CAPRAVIRINE

EXCRETED UNCHANGED

Comments:

The amount of unchanged capravirine in feces was low (0.4% of the dose for group A and 1.4% of the dose for group B)

Qualification:

FECAL

Amount:

[0.4 to 1.4] % (average)
of the dose


					A3Z87NSO0U

HUMAN IMMUNODEFICIENCY VIRUS TYPE 1 POLYMERASE

TARGET -> INHIBITOR

Amount:

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Related Record

Type

Details


					7U2NH9TAP8

5-((3,5-DICHLOROPHENYL)SULFINYL)-4-(1-METHYLETHYL)-1-(4-PYRIDINYLMETHYL)-1H-IMIDAZOLE-2-METHANOL 2-CARBAMATE

METABOLITE -> PARENT

Qualification:

FECAL; PLASMA; URINE

Amount:


					C06YW91KZ5

1H-IMIDAZOLE-2-METHANOL, 5-((3,5-DICHLOROPHENYL)SULFINYL)-4-(1-METHYLETHYL)-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, 2-CARBAMATE

METABOLITE -> PARENT

Qualification:

URINE

Amount:


					E3CEZ64VR2

1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)SULFINYL)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-(4-PYRIDINYLMETHYL)-, 2-CARBAMATE

METABOLITE -> PARENT

Qualification:

FECAL; URINE

Amount:


					WA2E3EQT7T

2-(2-(((AMINOCARBONYL)OXY)METHYL)-5-((3,5-DICHLOROPHENYL)SULFINYL)-1-(4-PYRIDINYLMETHYL)-1H-IMIDAZOL-4-YL)-1,2-PROPANEDIOL

METABOLITE -> PARENT

Qualification:

FECAL

Amount:


					EKR5H9BQ5Q

1H-IMIDAZOLE-2,4-DIMETHANOL, 5-((3,5-DICHLOROPHENYL)THIO)-.ALPHA.4,.ALPHA.4-DIMETHYL-1-((1-OXIDO-4-PYRIDINYL)METHYL)-, .ALPHA.2-CARBAMATE

METABOLITE -> PARENT

Qualification:

FECAL; URINE

Amount:

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Related Record

Type

Details


					VHC779598X

CAPRAVIRINE

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Parameters
Tmax	PHARMACOKINETIC	3 hours (average)	IN HEALTHY MALE VOLUNTEERS SINGLE DOSE 1400 mg (average) ORAL ADMINISTRATION

Biological Half-life	PHARMACOKINETIC	1.8 hours [1.6 to 2] (average)	ORAL ADMINISTRATION SINGLE DOSE 1400 mg (average) IN HEALTHY MALE VOLUNTEERS