abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+

Stable Identifier
R-HSA-2162078
Type
Reaction [transition]
Species
Homo sapiens
Compartment
cytosol
Synonyms
Oxidation of abacavir to abacavir 5'-carboxylate
ReviewStatus
5/5
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abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+
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Cytosolic ADH alpha dimer catalyzes the reaction of abacavir and NAD to form abacavir 5'-carboxylate and NADH + H+. Abacavir 5'-carboxylate is one of the major forms in which abacavir is excreted from the body. Studies with purified enzymes in vitro indicate that only the alpha isoform of ADH has this activity. These studies also suggest that the reaction proceeds in two steps via an unstable aldehyde intermediate (Walsh et al. 2002). Whether conversion of the aldehyde to the carboxylate is spontaneous or also catalyzed by ADH has not been established.
Literature References
PubMed ID Title Journal Year
12399160 The metabolic activation of abacavir by human liver cytosol and expressed human alcohol dehydrogenase isozymes

Walsh, JS, Reese, MJ, Thurmond, LM

Chem Biol Interact 2002
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Catalyst Activity

alcohol dehydrogenase (NAD+) activity of ADH1A:2Zn2+ dimer [cytosol]

Physical Entity
ADH1A:2Zn2+ dimer [cytosol] (Homo sapiens)
Activity
alcohol dehydrogenase (NAD+) activity (GO:0004022)
Orthologous Events
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Bos taurus)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Caenorhabditis elegans)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Canis familiaris)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Danio rerio)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Dictyostelium discoideum)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Drosophila melanogaster)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Gallus gallus)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Mus musculus)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Rattus norvegicus)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Saccharomyces cerevisiae)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Schizosaccharomyces pombe)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Sus scrofa)
abacavir + 2 NAD+ => abacavir 5'-carboxylate + 2 NADH + 2 H+ (Xenopus tropicalis)
Authored
D'Eustachio, P  (2012-03-14)
Reviewed
Jassal, B  (2012-03-16)
Created
D'Eustachio, P  (2012-03-14)
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