ent-Abacavir

CAS: 136470-79-6

Ref. TR-A105015

Product Information

• Name: ent-Abacavir
• Synonyms: (1R,4S)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol,(1R-cis)-4-[2-Amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol, (1R,4S)-Abacavir, Abacavir EP Impurity A, Abacavir Impurities, (1R,4S)-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]-, (1R,4S)-

Description

Impurity Abacavir EP Impurity A
Applications ent-Abacavir (Abacavir EP Impurity A) is an enatiomer 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: 286.33
• Formula: C₁₄H₁₈N₆O
• Color/Form: Neat
• InChI: InChI=1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m0/s1
• InChI key: InChIKey=MCGSCOLBFJQGHM-WCBMZHEXSA-N
• SMILES: Nc1nc(NC2CC2)c2ncn([C@@H]3C=C[C@H](CO)C3)c2n1