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
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
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
| Title | Date | PubMed |
|---|---|---|
| Potent and selective activity of a new carbocyclic nucleoside analog (carbovir: NSC 614846) against human immunodeficiency virus in vitro. | 1988 Oct 31 |
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| Resolution of racemic carbovir and selective inhibition of human immunodeficiency virus by the (-) enantiomer. | 1990 May 16 |
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| Carbovir: the (-) enantiomer is a potent and selective antiviral agent against human immunodeficiency virus in vitro. | 1991 Feb |
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| Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592U89. | 1997 May |
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| 1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity. | 1997 May |
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| Correlation of anti-HIV activity with structure: use of electrostatic potential and conformational analysis. | 1999 Jul 19 |
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| Metabolism of O6-propyl and N6-propyl-carbovir in CEM cells. | 2000 Apr |
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| Toxicity of antiviral nucleoside analogs and the human mitochondrial DNA polymerase. | 2001 Nov 2 |
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| Synthesis and conformational analysis of a locked analogue of carbovir built on a bicyclo[3.1.0]hex-2-enyl template. | 2003 Dec |
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| Toxicity of nucleoside analogues used to treat AIDS and the selectivity of the mitochondrial DNA polymerase. | 2003 Dec 23 |
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| 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 Aug 27 |
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| Membrane permeation characteristics of abacavir in human erythrocytes and human T-lymphoblastoid CD4+ CEM cells: comparison with (-)-carbovir. | 2004 Nov 1 |
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| Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents. | 2004 Sep |
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| Mechanism of anti-human immunodeficiency virus activity of beta-D-6-cyclopropylamino-2',3'-didehydro-2',3'-dideoxyguanosine. | 2005 May |
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| A combination of decreased NRTI incorporation and decreased excision determines the resistance profile of HIV-1 K65R RT. | 2005 Nov 4 |
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| Synthesis and antiviral evaluation of novel 6'(alpha)-methyl-branched Carbovir analogues. | 2005 Sep |
|
| Interaction of 2'-deoxyguanosine triphosphate analogue inhibitors of HIV reverse transcriptase with human mitochondrial DNA polymerase gamma. | 2007 |
Patents
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C97452
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FDA ORPHAN DRUG |
41189
Created by
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| Code System | Code | Type | Description | ||
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202940
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118353-05-2
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DTXSID00869614
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135433604
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614846
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421843
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05469V2RW8
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C1039
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PRIMARY |
ACTIVE MOIETY
