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Chemical Compound Review:

GAZT (2S,3S,4S,5R)-6-[[(2R)-3- azido-5-(5-methyl...

Synonyms: AC1L2Y25, 117675-21-5, AZT glucuronide, UNII-CD09F5JM6T, Zidovudine glucuronide

Meng, Q. et al., Anderson, P.L. et al., Cretton, E.M. et al., Hewitt, R.G. et al., Cordaro, J.A. et al., et al.

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Disease relevance of AZT glucuronide

STUDY OBJECTIVE: To characterize the concentration-time profiles of zidovudine and zidovudine-glucuronide in semen and serum of men infected with the human immunodeficiency-1 virus (HIV-1) [1].

High impact information on AZT glucuronide

A decreased plasma zidovudine-glucuronide/zidovudine ratio was noted after 1 week of GM-CSF, and an increase in the area under the plasma concentration-versus-time curve for zidovudine was found in three patients after 4 weeks [2].
AZT- and 3TC-specific radioimmunoassays (RIAs), or HPLC coupled with AZT-RIA, were used to measure plasma levels of AZT and the AZT-glucuronide, and cellular levels of AZT, phosphorylated AZT, and DNA incorporation of AZT or 3TC in cord blood mononuclear cells from treated infants compared with unexposed controls born to HIV-uninfected mothers [3].
Human kidney microsomes could also biosynthesize AZT glucuronide, although to a lower extent (six times less than the corresponding liver) [4].
The AZT-glucuronide was preliminarily identified through specific hydrolysis by beta-glucuronidase and rigorous product identification was performed by high-field proton nuclear magnetic resonance and fast-atom-bombardment mass spectrometry [5].
Semen and serum pharmacokinetics of zidovudine and zidovudine-glucuronide in men with HIV-1 infection [1].

Analytical, diagnostic and therapeutic context of AZT glucuronide

Zidovudine and zidovudine-glucuronide plasma concentrations were measured with radioimmunoassay to determine the pharmacokinetic characteristics during each menstrual phase [6].

References

Semen and serum pharmacokinetics of zidovudine and zidovudine-glucuronide in men with HIV-1 infection. Anderson, P.L., Noormohamed, S.E., Henry, K., Brundage, R.C., Balfour, H.H., Fletcher, C.V. Pharmacotherapy (2000) [Pubmed]
Pharmacokinetics and pharmacodynamics of granulocyte-macrophage colony-stimulating factor and zidovudine in patients with AIDS and severe AIDS-related complex. Hewitt, R.G., Morse, G.D., Lawrence, W.D., Maliszewski, M.L., Santora, J., Bartos, L., Bonnem, E., Poiesz, B. Antimicrob. Agents Chemother. (1993) [Pubmed]
Plasma and cellular markers of 3'-azido-3'-dideoxythymidine (AZT) metabolism as indicators of DNA damage in cord blood mononuclear cells from infants receiving prepartum NRTIs. Meng, Q., Olivero, O.A., Fasco, M.J., Bellisario, R., Kaminsky, L., Pass, K.A., Wade, N.A., Abrams, E.J., Nesel, C.J., Ness, R.B., Bigbee, W.L., O'neill, J.P., Walker, D.M., Poirier, M.C., Walker, V.E. Environ. Mol. Mutagen. (2007) [Pubmed]
Phenobarbital inducible UDP-glucuronosyltransferase is responsible for glucuronidation of 3'-azido-3'-deoxythymidine: characterization of the enzyme in human and rat liver microsomes. Haumont, M., Magdalou, J., Lafaurie, C., Ziegler, J.M., Siest, G., Colin, J.N. Arch. Biochem. Biophys. (1990) [Pubmed]
Glucuronidation of 3'-azido-3'-deoxythymidine by rat and human liver microsomes. Cretton, E.M., Waterhous, D.V., Bevan, R., Sommadossi, J.P. Drug Metab. Dispos. (1990) [Pubmed]
Zidovudine pharmacokinetics in HIV-positive women during different phases of the menstrual cycle. Cordaro, J.A., Morse, G.D., Bartos, L., Gugino, L.J., Maliszewski, M., Colomaio, R., Shelton, M., O'Donnell, A., Hewitt, R. Pharmacotherapy (1993) [Pubmed]

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