CAS:49805-30-3|rac 2-Azabicyclo[2.2.1]hept-5-en-3-one

Catalogue Number:A795200
Chemical Name:rac 2-Azabicyclo[2.2.1]hept-5-en-3-one
Synonyms:(+/-)-2-Azabicyclo[2.2.1]hept-5-en-3-one; (+/-)-Vince Lactam; Vince Lactam; Abacavir – In House Impurity; Abacavir Impurities
Impurity:Abacavir – In House Impurity:CAS Number:49805-30-3
Molecular Formula:C₆H₇NO
Melting Point:55-57°C
Molecular Weight:109.13
Storage:4°C
Category:Building Blocks; Miscellaneous;
Applications:rac 2-Azabicyclo[2.2.1]hept-5-en-3-one (Abacavir – In House Impurity) is a useful reagent in the synthesis of carbocyclic sugar amines, carbanucleosides, and carbocyclic dinucleotide analogues (1). rac 2-Azabicyclo[2.2.1]hept-5-en-3-one is also an intermediate of Abacavir (A104990), a carbocyclic 2′-deoxyguanosine nucleoside reverse transcriptase inhibitor and 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) Slama, J.T., et al.: Biochemistry, 27, 183 (1988)
(2) Jackson, A., et al.: Antivir Ther. 17, 19 (2012)
(3) Yuen, G. J., et al.: Clin Pharmacokinet. 47, 351 (2008)
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