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 |
|---|---|---|
| Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides. | 1990 Jan |
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| Evaluation of synergy between carbovir and 3'-azido-2',3'-deoxythymidine for inhibition of human immunodeficiency virus type 1. | 1993 Jan |
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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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| Direct analysis of a polar pharmaceutical compound in plasma using ultra-high flow rate liquid chromatography/mass spectrometry with a mixed-mode column. | 2001 |
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| Toxicity of antiviral nucleoside analogs and the human mitochondrial DNA polymerase. | 2001 Nov 2 |
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| Antiviral activity of cyclosaligenyl prodrugs of acyclovir, carbovir and abacavir. | 2001 Sep |
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| Synthesis of novel hydroxymethyl substituted analogues related to carbovir and neplanocin A. | 2002 |
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| Pd asymmetric allylic alkylation (AAA). A powerful synthetic tool. | 2002 Jan |
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| Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent. | 2002 Mar |
|
| 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 |
|
| 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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| 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 Jul 25 |
|
| Synthesis, antiviral activity, and mechanism of drug resistance of D- and L-2',3'-didehydro-2',3'-dideoxy-2'-fluorocarbocyclic nucleosides. | 2005 Jun 2 |
|
| Mechanism of anti-human immunodeficiency virus activity of beta-D-6-cyclopropylamino-2',3'-didehydro-2',3'-dideoxyguanosine. | 2005 May |
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| Synthesis and antiviral evaluation of novel 6'(alpha)-methyl-branched Carbovir analogues. | 2005 Sep |
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| Synthesis of carbovir and abacavir from a carbocyclic precursor. | 2006 Jul |
|
| Mitochondrial toxicity of tenofovir, emtricitabine and abacavir alone and in combination with additional nucleoside reverse transcriptase inhibitors. | 2007 |
|
| Efficient synthesis of 4'-cyclopropylated carbovir analogues with use of ring-closing metathesis from glycolate. | 2008 Oct |
|
| Abacavir pharmacokinetics during chronic therapy in HIV-1-infected adolescents and young adults. | 2009 Apr |
|
| The triple combination of tenofovir, emtricitabine and efavirenz shows synergistic anti-HIV-1 activity in vitro: a mechanism of action study. | 2009 May 13 |
|
| Raltegravir is a potent inhibitor of XMRV, a virus implicated in prostate cancer and chronic fatigue syndrome. | 2010 Apr 1 |
|
| Cellular pharmacology and potency of HIV-1 nucleoside analogs in primary human macrophages. | 2013 Mar |
Patents
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C97452
Created by
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FDA ORPHAN DRUG |
41189
Created by
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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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ACTIVE MOIETY
