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© Research
Publication : Journal of medicinal chemistry

Improved brain delivery of AZT using a glycosyl phosphotriester prodrug

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Journal of medicinal chemistry - 01 Aug 1992

Namane A, Gouyette C, Fillion MP, Fillion G, Huynh-Dinh T

Link to Pubmed [PMID] – 1501232

J. Med. Chem. 1992 Aug;35(16):3039-44

The concentration of AZT in mice plasma and brain was measured using HPLC after an ingestion of 20 mg/kg of AZT or the molar equivalent of hexadecyl 2-(alpha-D-mannopyranosidyl)ethyl 3′-azido-3′-deoxy-5′-thymidinyl phosphate 3. The results demonstrated the promising qualities of the prodrug 3 which gave AZT-5′-phosphate as the main metabolite: the total concentration of AZT derivatives detected in brain presented a peak of 156 nmol/g (5 nmol/g for AZT) at 1 h; the half-life was about 24 h (1 h for AZT) with an AUC of 4366 nmol h/g as compared to 4 nmol h/g for AZT. The lipophilic properties of 3 were confirmed by its in vitro transport of inside synaptosomes. The derivative 2-(alpha-D-mannopyranosidyl)ethyl 3′-azido-3′-deoxy-5′-thymidinyl phosphate (2) provided also a good delivery of AZT to the central nervous system, with values intermediate between those of AZT and 3.

http://www.ncbi.nlm.nih.gov/pubmed/1501232