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Details

Stereochemistry RACEMIC
Molecular Formula C11H13N5O2
Molecular Weight 247.2532
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBOVIR

SMILES

NC1=NC2=C(N=CN2[C@@H]3C[C@H](CO)C=C3)C(=O)N1

InChI

InChIKey=XSSYCIGJYCVRRK-RQJHMYQMSA-N
InChI=1S/C11H13N5O2/c12-11-14-9-8(10(18)15-11)13-5-16(9)7-2-1-6(3-7)4-17/h1-2,5-7,17H,3-4H2,(H3,12,14,15,18)/t6-,7+/m1/s1

HIDE SMILES / InChI
Carbovir is a nucleoside reverse transcriptase inhibitor analog of guanosine. Carbovir decreases HIV viral loads, retards or prevents the damage to the immune system, and reduces the risk of developing AIDS. Carbovir Triphosphate belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. Carbovir interferes with the enzyme HIV uses to manufacture new viral particles within an infected cell, and is primarily metabolized to the 5'-triphosphate of Carbovir (CBV-TP) to concentrations sufficient to inhibit HIV reverse transcriptase.

Approval Year

PubMed

PubMed

TitleDatePubMed
Cellular pharmacology and potency of HIV-1 nucleoside analogs in primary human macrophages.
2013-03
Raltegravir is a potent inhibitor of XMRV, a virus implicated in prostate cancer and chronic fatigue syndrome.
2010-04-01
The triple combination of tenofovir, emtricitabine and efavirenz shows synergistic anti-HIV-1 activity in vitro: a mechanism of action study.
2009-05-13
Abacavir pharmacokinetics during chronic therapy in HIV-1-infected adolescents and young adults.
2009-04
Efficient synthesis of 4'-cyclopropylated carbovir analogues with use of ring-closing metathesis from glycolate.
2008-10
Synthesis and anti-HIV study of novel acyclic guanine derivatives.
2008-02
Specificity enhancement with LC-positive ESI-MS/MS for the measurement of nucleotides: application to the quantitative determination of carbovir triphosphate, lamivudine triphosphate and tenofovir diphosphate in human peripheral blood mononuclear cells.
2008-02
Syntheses and anti-HIV activities of (+/-)-norcarbovir and (+/-)-norabacavir.
2007-04-21
D- and L-2',3'-didehydro-2',3'-dideoxy-3'-fluoro-carbocyclic nucleosides: synthesis, anti-HIV activity and mechanism of resistance.
2007-04-19
Synthesis of novel 2'-methyl carbovir analogues as potent antiviral agents.
2007-02
Mitochondrial toxicity of tenofovir, emtricitabine and abacavir alone and in combination with additional nucleoside reverse transcriptase inhibitors.
2007
Interaction of 2'-deoxyguanosine triphosphate analogue inhibitors of HIV reverse transcriptase with human mitochondrial DNA polymerase gamma.
2007
Synthesis of carbovir and abacavir from a carbocyclic precursor.
2006-07
N6-methyl-AMP aminohydrolase activates N6-substituted purine acyclic nucleoside phosphonates.
2006-04-28
A combination of decreased NRTI incorporation and decreased excision determines the resistance profile of HIV-1 K65R RT.
2005-11-04
Synthesis and antiviral evaluation of novel 6'(alpha)-methyl-branched Carbovir analogues.
2005-09
Intracellular pharmacokinetics of tenofovir diphosphate, carbovir triphosphate, and lamivudine triphosphate in patients receiving triple-nucleoside regimens.
2005-08-01
Simultaneous analysis of several antiretroviral nucleosides in rat-plasma by high-performance liquid chromatography with UV using acetic acid/hydroxylamine buffer Test of this new volatile medium-pH for HPLC-ESI-MS/MS.
2005-07-25
Synthesis, antiviral activity, and mechanism of drug resistance of D- and L-2',3'-didehydro-2',3'-dideoxy-2'-fluorocarbocyclic nucleosides.
2005-06-02
Application of phosphoramidate pronucleotide technology to abacavir leads to a significant enhancement of antiviral potency.
2005-05-19
Mechanism of anti-human immunodeficiency virus activity of beta-D-6-cyclopropylamino-2',3'-didehydro-2',3'-dideoxyguanosine.
2005-05
Membrane permeation characteristics of abacavir in human erythrocytes and human T-lymphoblastoid CD4+ CEM cells: comparison with (-)-carbovir.
2004-11-01
Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents.
2004-09
Improved antiviral activity of the aryloxymethoxyalaninyl phosphoramidate (APA) prodrug of abacavir (ABC) is due to the formation of markedly increased carbovir 5'-triphosphate metabolite levels.
2004-08-27
Toxicity of nucleoside analogues used to treat AIDS and the selectivity of the mitochondrial DNA polymerase.
2003-12-23
Synthesis and conformational analysis of a locked analogue of carbovir built on a bicyclo[3.1.0]hex-2-enyl template.
2003-12
Recent advances in the synthesis of conformationally locked nucleosides and their success in probing the critical question of conformational preferences by their biological targets.
2003-10-21
Structural determinants in human DNA polymerase gamma account for mitochondrial toxicity from nucleoside analogs.
2003-05-23
New progresses in the enantioselective synthesis and biological properties of carbocyclic nucleosides.
2003-03
Structural characterization of the closed conformation of mouse guanylate kinase.
2002-08-16
Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent.
2002-03
Pd asymmetric allylic alkylation (AAA). A powerful synthetic tool.
2002-01
Synthesis of novel hydroxymethyl substituted analogues related to carbovir and neplanocin A.
2002
Toxicity of antiviral nucleoside analogs and the human mitochondrial DNA polymerase.
2001-11-02
Antiviral activity of cyclosaligenyl prodrugs of acyclovir, carbovir and abacavir.
2001-09
Direct analysis of a polar pharmaceutical compound in plasma using ultra-high flow rate liquid chromatography/mass spectrometry with a mixed-mode column.
2001
Metabolism of O6-propyl and N6-propyl-carbovir in CEM cells.
2000-04
Correlation of anti-HIV activity with structure: use of electrostatic potential and conformational analysis.
1999-07-19
Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592U89.
1997-05
1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity.
1997-05
Evaluation of synergy between carbovir and 3'-azido-2',3'-deoxythymidine for inhibition of human immunodeficiency virus type 1.
1993-01
Carbovir: the (-) enantiomer is a potent and selective antiviral agent against human immunodeficiency virus in vitro.
1991-02
Resolution of racemic carbovir and selective inhibition of human immunodeficiency virus by the (-) enantiomer.
1990-05-16
Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides.
1990-01
Potent and selective activity of a new carbocyclic nucleoside analog (carbovir: NSC 614846) against human immunodeficiency virus in vitro.
1988-10-31
Patents
Name Type Language
CARBOVIR
Common Name English
GR-90352X
Preferred Name English
NSC-614846
Code English
6H-PURIN-6-ONE, 2-AMINO-1,9-DIHYDRO-9-((1R,4S)-4-(HYDROXYMETHYL)-2-CYCLOPENTEN-1-YL)-, REL-
Common Name English
CARBOVIR, (±)-
Common Name English
(±)-CARBOVIR
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C97452
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
FDA ORPHAN DRUG 41189
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
Code System Code Type Description
CHEBI
202940
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
PRIMARY
CAS
118353-05-2
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID00869614
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
PRIMARY
NSC
614846
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
PRIMARY
CHEBI
421843
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
PRIMARY
FDA UNII
05469V2RW8
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
PRIMARY
NCI_THESAURUS
C1039
Created by admin on Mon Mar 31 21:41:32 GMT 2025 , Edited by admin on Mon Mar 31 21:41:32 GMT 2025
PRIMARY