Abacavir 5’-Beta-D-Glucuronide Sodium Salt

CAS: 384329-76-4

Ref. TR-A104985

Product Information

• Name: Abacavir 5’-Beta-D-Glucuronide Sodium Salt
• Synonyms: [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl]methyl-ß-D-Glucopyranosiduronic Acid Sodium Salt, Abacavir 5’-Glucuronide Sodium Salt

Description

Stability Hygroscopic
Applications Abacavir 5’-β-D-Glucuronide is a metabolite of Abacavir (A105000). Abacavir is a carbocyclic 2'-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.
References (1) Jackson, A., et al.: Antivir Ther. 17, 19 (2012) (2) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)

• Brand: TRC

Chemical properties

• Molecular weight: 484.44
• Formula: C₂₀H₂₅N₆NaO₇
• Color/Form: Neat
• InChI: InChI=1S/C20H26N6O7.Na/c21-20-24-16(23-9-2-3-9)11-17(25-20)26(7-22-11)10-4-1-8(5-10)6-32-19-14(29)12(27)13(28)15(33-19)18(30)31;/h1,4,7-10,12-15,19,27-29H,2-3,5-6H2,(H,30,31)(H3,21,23,24,25);/q;+1/p-1/t8-,10+,12+,13+,14-,15+,19-;/m1./s1
• InChI key: InChIKey=JCJOXVVHKQGGPY-AGFQZUHLSA-M
• SMILES: Nc1nc(NC2CC2)c2ncn([C@H]3C=C[C@@H](CO[C@@H]4O[C@H](C(=O)O[Na])[C@@H](O)[C@H](O)[C@H]4O)C3)c2n1