Abacavir

Modify Date: 2024-01-02 17:12:36

Abacavir Structure
Abacavir structure
Common Name Abacavir
CAS Number 136470-78-5 Molecular Weight 286.332
Density 1.7±0.1 g/cm3 Boiling Point 636.0±65.0 °C at 760 mmHg
Molecular Formula C14H18N6O Melting Point 161 °C(dec.)
MSDS N/A Flash Point 338.4±34.3 °C

 Use of Abacavir


Abacavir is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. IC50 value:Target: NRTI; reverse transcriptase inhibitorAbacavir is a nucleoside reverse transcriptase inhibitor marketed since 1999 for the treatment of infection with the human immunodeficiency virus type 1 (HIV). Despite its clinical efficacy, abacavir administration has been associated with serious and sometimes fatal toxic events. Abacavir has been reported to undergo bioactivation in vitro, yielding reactive species that bind covalently to human serum albumin, but the haptenation mechanism and its significance to the toxic events induced by this anti-HIV drug have yet to be elucidated. The mechanism underlying abacavir hypersensitivity syndrome is related to the change in the HLA-B*5701 protein product. Abacavir binds with high specificity to the HLA-B*5701 protein, changing the shape and chemistry of the antigen-binding cleft. This results in a change in immunological tolerance and the subsequent activation of abacavir-specific cytotoxic T cells, which produce a systemic reaction known as abacavir hypersensitivity syndrome.

 Names

Name abacavir
Synonym More Synonyms

 Abacavir Biological Activity

Description Abacavir is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. IC50 value:Target: NRTI; reverse transcriptase inhibitorAbacavir is a nucleoside reverse transcriptase inhibitor marketed since 1999 for the treatment of infection with the human immunodeficiency virus type 1 (HIV). Despite its clinical efficacy, abacavir administration has been associated with serious and sometimes fatal toxic events. Abacavir has been reported to undergo bioactivation in vitro, yielding reactive species that bind covalently to human serum albumin, but the haptenation mechanism and its significance to the toxic events induced by this anti-HIV drug have yet to be elucidated. The mechanism underlying abacavir hypersensitivity syndrome is related to the change in the HLA-B*5701 protein product. Abacavir binds with high specificity to the HLA-B*5701 protein, changing the shape and chemistry of the antigen-binding cleft. This results in a change in immunological tolerance and the subsequent activation of abacavir-specific cytotoxic T cells, which produce a systemic reaction known as abacavir hypersensitivity syndrome.
Related Catalog
References

[1]. Charneira C, et al. Reactive aldehyde metabolites from the anti-HIV drug abacavir: amino acid adducts as possible factors in abacavir toxicity. Chem Res Toxicol. 2011 Dec 19;24(12):2129-41.

[2]. Hervey PS, et al. Abacavir: a review of its clinical potential in patients with HIV infection. Drugs. 2000 Aug;60(2):447-79.

 Chemical & Physical Properties

Density 1.7±0.1 g/cm3
Boiling Point 636.0±65.0 °C at 760 mmHg
Melting Point 161 °C(dec.)
Molecular Formula C14H18N6O
Molecular Weight 286.332
Flash Point 338.4±34.3 °C
Exact Mass 286.154205
PSA 101.88000
LogP 0.72
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.864
Storage condition 0-6°C

 Synthetic Route

 Synonyms

MFCD00903850
(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol
(1S,cis)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol
2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S,4R)-
Abacavir
2-Cyclopentene-1-methanol, 4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-, (1S,4R)-
2-Cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S-cis)-
{(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl}methanol
{(1S,4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol
{(4R)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol
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