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3'-Azido-3'-deoxythymidine β-D-glucuronide (sodium salt) (Synonyms: AZT glucuronide,Zidovudine glucuronide)

Catalog No.GC10387

Zidovudine O-β-D-glucuronide (3'-Azido-3'-deoxythymidine β-D-glucuronide) sodium is the major metabolite of Zidovudine.

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

Cas No.: 133525-01-6

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Sample solution is provided at 25 µL, 10mM.

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

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

Cas No. 133525-01-6 SDF
Synonyms AZT glucuronide,Zidovudine glucuronide
Chemical Name 3'-azido-3'-deoxy-5'-O-β-D-glucopyranuronosyl-thymidine, monosodium salt
Canonical SMILES O=C([O-])[C@@H](O1)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC[C@@H]2[C@@H](N=[N+]=[N-])C[C@H](N3C=C(C)C(NC3=O)=O)O2.[Na+]
Formula C16H20N5O10 • Na M.Wt 465.4
Solubility ≤0.5mg/ml in DMSO Storage Store at 2-8°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 3'-Azido-3'-deoxythymidine β-D-glucuronide (sodium salt)

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1 mg 5 mg 10 mg
1 mM 2.1487 mL 10.7434 mL 21.4869 mL
5 mM 0.4297 mL 2.1487 mL 4.2974 mL
10 mM 0.2149 mL 1.0743 mL 2.1487 mL
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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

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