3'-AZIDO-3'-DEOXYTHYMIDINE BETA-D-GLUCURONIDE, SODIUM SALT Chemical Properties

Melting point:

158-163°C

storage temp. 

-20°C Freezer, Under Inert Atmosphere

solubility 

DMSO (Slightly, Heated, Sonicated), Methanol (Very Slightly, Heated), Water (Slightly)

form 

Solid

color 

White to Light Yellow

Stability:

Hygroscopic

3'-AZIDO-3'-DEOXYTHYMIDINE BETA-D-GLUCURONIDE, SODIUM SALT Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

A metabolite of the potent and selective inhibitor of HIV-1 replication, AZT

Biological Activity

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].

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.

3'-AZIDO-3'-DEOXYTHYMIDINE BETA-D-GLUCURONIDE, SODIUM SALT(133525-01-6)Related Product Information

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