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

In stock
Catalog No.
C3806
metabolite of the nucleoside reverse transcriptase inhibitor, zidovudine
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SizePriceStock Qty
1mg
$59.00
In stock
5mg
$148.00
In stock
10mg
$253.00
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3'-Azido-3'-deoxythymidine β-D-glucuronide is the metabolite of zidovudine, a nucleoside reverse transcriptase inhibitor.

Zidovudine, an antiretroviral medication used to prevent and treat HIV, is recommended for use with other antiretroviral and may be also used to prevent mother to child spread during birth or after a needlestick injury or other potential exposure.

In vitro: 3'-Azido-3'-deoxythymidine β-D-glucuronide is a metabolite of zidovudine, formed by direct conjugation by UDP-glucuronosyltransferase 2B7. The azido group of both zidovudine and 3'-azido-3'-deoxythymidine β-D-glucuronide could be reduced to an amino group by cytochrome CYP3A, CYP2A6, or CYP2B1, forming 3’-amino-3’-deoxythymidine (AMT) and AMT glucuronide, respectively [1].

In vivo: Animal study found that zidovudine-treated rats had higher systolic blood pressure, greater heart weight and greater interventricular septum thickness. Electron microscopy revealed mitochondrial swelling in myocardiocytes in zidovudine-treated rats. Reduced response to contractile stimuli and enhanced relaxation in response to charbacol were observed in the aortic rings of zidovudine-treated rats. The aortic myocytes of zidovudine-treated rats contained apparently unaffected ultrastructural features, but light microscopy suggested their marked enlargement [2].

Clinical trial: So far, no clinical study has been conducted.

References:
[1] Walsky, R. L.,Bauman, J.N.,Bourcier, K., et al. Optimized assays for human UDP-glucuronosyltransferase (UGT) activities: altered alamethicin concentration and utility to screen for UGT inhibitors. Drug Metabolism and Disposition 40(5), 1051-1065 (2012).
[2] Ruga E, Bova S, Nussdorfer G, Mazzocchi G, Rebuffat P, Milanesi O, Cargnelli G.  Zidovudine-induced alterations in the heart and vascular smooth muscle of the rat. Cardiovasc Res. 2003 Oct 15;60(1):147-55.

Chemical Properties

Physical AppearanceA crystalline solid
StorageStore at -20°C
M.Wt465.4
Cas No.133525-01-6
FormulaC16H20N5O10 • Na
SynonymsAZT glucuronide,Zidovudine glucuronide
Solubility≤0.5mg/ml in DMSO
Chemical Name3'-azido-3'-deoxy-5'-O-β-D-glucopyranuronosyl-thymidine, monosodium salt
SDFDownload SDF
Canonical SMILESO=C([O-])[[email protected]@H](O1)[[email protected]@H](O)[[email protected]](O)[[email protected]@H](O)[[email protected]@H]1OC[[email protected]@H]2[[email protected]@H](N=[N+]=[N-])C[[email protected]](N3C=C(C)C(NC3=O)=O)O2.[Na+]
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Quality Control

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Chemical structure

3