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)
Molecular Formula | C20H20Cl2N4O2S |
Molecular Weight | 451.369 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
S-1153 inhibits replication of known drug-resistant strains of human immunodeficiency virus type 1. | 1998 Jun |
|
Structural determination of metabolites of S-1153, a new, potent, non-nucleoside, anti-HIV agent in rat liver microsomes. | 1998 Sep |
|
Capravirine trials stopped. | 2001 Apr |
|
Antiviral drugs: current state of the art. | 2001 Aug |
|
Highlights in the development of new antiviral agents. | 2002 Apr |
|
Gateways to clinical trials. | 2002 Dec |
|
Gateways to clinical trials. | 2003 Nov |
|
Current status of the non-nucleoside reverse transcriptase inhibitors of human immunodeficiency virus type 1. | 2004 |
|
Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future. | 2004 Jan |
|
Metabolism and excretion of capravirine, a new non-nucleoside reverse transcriptase inhibitor, alone and in combination with ritonavir in healthy volunteers. | 2004 Jul |
|
New antiretroviral agents for the treatment of HIV infection. | 2004 Jun |
|
New targets and new drugs in the treatment of HIV. | 2005 Jul |
|
New drugs. | 2005 Jul |
|
Gateways to clinical trials. | 2005 Jun |
|
Emerging anti-HIV drugs. | 2005 May |
|
A lame duck, a dark horse, and a goat. | 2005 May-Jun |
|
A simple sequential incubation method for deconvoluting the complicated sequential metabolism of capravirine in humans. | 2005 Oct |
|
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 2). | 2006 Dec |
|
Arylthiopyrrole (AThP) derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors: synthesis, structure-activity relationships, and docking studies (part 1). | 2006 Dec |
|
Identification of enzymes responsible for primary and sequential oxygenation reactions of capravirine in human liver microsomes. | 2006 Nov |
|
N2-benzyloxycarbonylguan-9-yl acetic acid derivatives as HIV-1 reverse transcriptase non-nucleoside inhibitors with decreased loss of potency against common drug-resistance mutations. | 2007 Oct |
|
Evaluation of capravirine as a CYP3A probe substrate: in vitro and in vivo metabolism of capravirine in rats and dogs. | 2007 Sep |
|
Ritonavir 100 mg does not cause QTc prolongation in healthy subjects: a possible role as CYP3A inhibitor in thorough QTc studies. | 2008 Jan |
|
Conformational landscape of the human immunodeficiency virus type 1 reverse transcriptase non-nucleoside inhibitor binding pocket: lessons for inhibitor design from a cluster analysis of many crystal structures. | 2009 Oct 22 |
|
Amino acid derivatives, part 4: synthesis and anti-HIV activity of new naphthalene derivatives. | 2010 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00004985
1400 mg twice daily
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:13:43 UTC 2023
by
admin
on
Fri Dec 15 16:13:43 UTC 2023
|
Record UNII |
VHC779598X
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C97453
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID30170689
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
1783
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
m1053
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | Merck Index | ||
|
VHC779598X
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
178979-85-6
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
DB08502
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
C81612
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
7980
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
CHEMBL435128
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
CAPRAVIRINE
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
KK-73
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
SUB20328
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY | |||
|
100000078028
Created by
admin on Fri Dec 15 16:13:43 UTC 2023 , Edited by admin on Fri Dec 15 16:13:43 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET ORGANISM->INHIBITOR |
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
||
|
EXCRETED UNCHANGED |
Excretion of unchanged capravirine was negligible in urine.
URINE
|
||
|
EXCRETED UNCHANGED |
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)
FECAL
|
||
|
TARGET -> INHIBITOR |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
FECAL; PLASMA; URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
FECAL; URINE
|
||
|
METABOLITE -> PARENT |
FECAL
|
||
|
METABOLITE -> PARENT |
FECAL; URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
||
|
METABOLITE -> PARENT |
FECAL
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
MAJOR
PLASMA
|
||
|
METABOLITE -> PARENT |
FECAL
|
||
|
METABOLITE -> PARENT |
PLASMA; URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Tmax | PHARMACOKINETIC |
|
IN HEALTHY MALE VOLUNTEERS |
|
||
Biological Half-life | PHARMACOKINETIC |
|
ORAL ADMINISTRATION |
|
||