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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H13N5O2
Molecular Weight 247.2532
Optical Activity UNSPECIFIED
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
Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides.
1990 Jan
Unique intracellular activation of the potent anti-human immunodeficiency virus agent 1592U89.
1997 May
1592U89, a novel carbocyclic nucleoside analog with potent, selective anti-human immunodeficiency virus activity.
1997 May
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
Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents.
2004 Sep
Mechanism of anti-human immunodeficiency virus activity of beta-D-6-cyclopropylamino-2',3'-didehydro-2',3'-dideoxyguanosine.
2005 May
Synthesis and antiviral evaluation of novel 6'(alpha)-methyl-branched Carbovir analogues.
2005 Sep
Syntheses and anti-HIV activities of (+/-)-norcarbovir and (+/-)-norabacavir.
2007 Apr 21
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 Feb
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
Name Type Language
CARBOVIR, (-)-
Common Name English
6H-PURIN-6-ONE, 2-AMINO-1,9-DIHYDRO-9-((1R,4S)-4-(HYDROXYMETHYL)-2-CYCLOPENTEN-1-YL)-
Systematic Name English
(-)-CARBOVIR
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID50152861
Created by admin on Fri Dec 15 21:20:46 GMT 2023 , Edited by admin on Fri Dec 15 21:20:46 GMT 2023
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FDA UNII
51560211J4
Created by admin on Fri Dec 15 21:20:46 GMT 2023 , Edited by admin on Fri Dec 15 21:20:46 GMT 2023
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CAS
120443-30-3
Created by admin on Fri Dec 15 21:20:46 GMT 2023 , Edited by admin on Fri Dec 15 21:20:46 GMT 2023
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PUBCHEM
135433604
Created by admin on Fri Dec 15 21:20:46 GMT 2023 , Edited by admin on Fri Dec 15 21:20:46 GMT 2023
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