CARBOVIR

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 Search

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

Molecular Formula	C11H13N5O2
Molecular Weight	247.2532
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://pubchem.ncbi.nlm.nih.gov/compound/Carbovir | http://www.hmdb.ca/metabolites/HMDB0061723 | https://www.ncbi.nlm.nih.gov/pubmed/7685993

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
Metabolism of O6-propyl and N6-propyl-carbovir in CEM cells.	2000 Apr	10960036
Direct analysis of a polar pharmaceutical compound in plasma using ultra-high flow rate liquid chromatography/mass spectrometry with a mixed-mode column.	2001	11746927
Toxicity of antiviral nucleoside analogs and the human mitochondrial DNA polymerase.	2001 Nov 2	11526116
Antiviral activity of cyclosaligenyl prodrugs of acyclovir, carbovir and abacavir.	2001 Sep	11900349
Structural characterization of the closed conformation of mouse guanylate kinase.	2002 Aug 16	12036965
Novel use of a guanosine prodrug approach to convert 2',3'-didehydro-2',3'-dideoxyguanosine into a viable antiviral agent.	2002 Mar	11850281
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	15327972
D- and L-2',3'-didehydro-2',3'-dideoxy-3'-fluoro-carbocyclic nucleosides: synthesis, anti-HIV activity and mechanism of resistance.	2007 Apr 19	17373782
Syntheses and anti-HIV activities of (+/-)-norcarbovir and (+/-)-norabacavir.	2007 Apr 21	17406712
Synthesis of novel 2'-methyl carbovir analogues as potent antiviral agents.	2007 Feb	17366731

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 07:27:57 GMT 2023` Edited by `admin` on `Sat Dec 16 07:27:57 GMT 2023`
Record UNII	05469V2RW8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARBOVIR

Common 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

GR-90352X

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C97452