Zidovudine O-β-D-glucuronide (sodium)

Zidovudine O-β-D-glucuronide (3'-Azido-3'-deoxythymidine β-D-glucuronide) sodium is the major metabolite of Zidovudine. Zidovudine is a nucleoside reverse transcriptase inhibitor (NRTI), widely used to treat HIV infection[1][2]. Zidovudine O-β-D-glucuronide (sodium) is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.

Product Specifications

CAS Number

[133525-01-6]

Product Name Alternative

3'-Azido-3'-deoxythymidine β-D-glucuronide (sodium)

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Drug Metabolite

Type

Reference compound

Related Pathways

Metabolic Enzyme/Protease

Field of Research

Others

Assay Protocol

https://www.medchemexpress.com/zidovudine-o-β-d-glucuronide-sodium.html

Purity

99.05

Solubility

DMSO : 100 mg/mL (ultrasonic; warming; heat to 60°C)

Smiles

O=C(NC1=O)N(C=C1C)[C@](C[C@@H]2N=[N+]=[N-])([H])O[C@@H]2CO[C@@H]([C@@H]([C@H]3O)O)O[C@@H]([C@H]3O)C(O[Na])=O

Molecular Formula

C16H20N5NaO10

Molecular Weight

465.35

Precautions

H302, H315, H319, H335

References & Citations

[1]Fayz S, et, al. Zidovudine azido-reductase in human liver microsomes: activation by ethacrynic acid, dipyridamole, and indomethacin and inhibition by human immunodeficiency virus protease inhibitors. Antimicrob Agents Chemother. 1998 Jul;42 (7) :1654-8. |[2]Bélanger AS, et, al. Glucuronidation of the antiretroviral drug efavirenz by UGT2B7 and an in vitro investigation of drug-drug interaction with zidovudine. Drug Metab Dispos. 2009 Sep;37 (9) :1793-6.