(1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol D-Tartrate

CAS: 229177-52-0

Ref. TR-A603640

Product Information

• Name: (1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol D-Tartrate
• Synonyms: [(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol;(2S,3S)-2,3-dihydroxybutanedioic acid, (1S,4R)-4-Amino-2-cyclopentene-1-methanol (2S,3S)-2,3-dihydroxybutanedioate (1:1) salt, (1S-cis)-4-Amino-2-cyclopentene-1-menthanol D-hydrogen tatrate, 2-Cyclopentene-1-methanol, 4-amino-, (1S,4R)-, (2S,3S)-2,3-dihydroxybutanedioate (1:1) (salt), [(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol 2,3-dihydroxybutanedioate (1:1)

Description

Impurity Abacavir - In House Impurity
Applications (1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol D-Tartrate (Abacavir - In House Impurity) is an intermediate of Abacavir (A104990). 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: 263.24
• Formula: C₆H₁₁NO·C₄H₆O₆
• Color/Form: Neat
• InChI: InChI=1S/C6H11NO.C4H6O6/c7-6-2-1-5(3-6)4-8;5-1(3(7)8)2(6)4(9)10/h1-2,5-6,8H,3-4,7H2;1-2,5-6H,(H,7,8)(H,9,10)/t5-,6+;1-,2-/m10/s1
• InChI key: InChIKey=LTSTZOJHLZNDFG-ZGMNSGLWSA-N
• SMILES: N[C@H]1C=C[C@@H](CO)C1.O=C(O)[C@@H](O)[C@H](O)C(=O)O