Abacavir 5’-Phosphate

CAS: 136470-77-4

Ref. TR-A105020

Product Information

• Name: Abacavir 5’-Phosphate
• Synonyms: (1S,4R)- 4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanolDihydrogen Phosphate (Ester), (1S-cis)-Abacavir Monophosphate, Abacavir - In House Impurity, Abacavir Impurities, Abacavir Metabolites

Description

Impurity Abacavir - In House Impurity
Applications Abacavir 5’-Phosphate (Abacavir - In House Impurity) 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: 366.31
• Formula: C₁₄H₁₉N₆O₄P
• Color/Form: White Solid
• InChI: InChI=1S/C14H19N6O4P/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-24-25(21,22)23/h1,4,7-10H,2-3,5-6H2,(H2,21,22,23)(H3,15,17,18,19)/t8-,10+/m1/s1
• InChI key: InChIKey=YQBOXVWMECPEJS-SCZZXKLOSA-N
• SMILES: Nc1nc(NC2CC2)c2ncn([C@H]3C=C[C@@H](COP(=O)(O)O)C3)c2n1