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dc.contributor.authorLegoabe, Lesetja J.en_US
dc.contributor.authorN'Da, David D.en_US
dc.contributor.authorBreytenbach, Jaco C.en_US
dc.contributor.authorDu Preez, Jan L.en_US
dc.contributor.authorDu Plessis, Jeanettaen_US
dc.identifier.citationLegoabe, L.J. et al. 2010. Synthesis and transdermal permeation of novel N4-methoxypoly(ethylene glycol) carbamates of cytarabine. Drug development and industrial pharmacy, 36(12):1477-1485. []en_US
dc.identifier.issn1520-5762 (Online)en_US
dc.description.abstractBackground: Cytarabine is a deoxycytidine analogue commonly used in the treatment of hematological malignant diseases. Its clinical utility, however, is severely limited by its short plasma half-life because of the catabolic action of nucleoside deaminases. Method: In this study, N4-carbamate derivatives of cytarabine (1) were synthesized and evaluated for transdermal penetration because this mode of administration may circumvent its limitations. The synthesis of these compounds was achieved in a two-step process. First, the methoxypoly(ethylene glycol) was activated by p-nitrophenyl chloroformate. Second, the activated intermediates were reacted with cytarabine in the presence of N-hydroxysuccinamide to give the N4-methoxypoly(ethylene glycol) carbamate derivatives. The transdermal flux values of the N4-carbamates of cytarabine were determined in vitro by Franz diffusion cell methodology. Aqueous solubility and log D (pH 7.4) values were determined and assessed for correlation with transdermal flux values. Results: The synthesized carbamates, particularly, (9)–(13), showed increased solubility in both aqueous and lipid media. Log D values decreased as the oxyethylene chain lengthened. Conclusion: Although none of the derivatives showed significantly higher transdermal penetration than cytarabine (1), it should be mentioned that the mean for cytarabine N4-methoxyethyleneoxycarbamate (8) was 10 times higher and the median was 2 times higher
dc.publisherTaylor & Francisen_US
dc.subjectLog D
dc.subjectMethoxypoly(ethylene glycol)
dc.subjectPercutaneous absorption
dc.subjectPhysicochemical properties
dc.subjectSkin penetration
dc.subjectTransdermal delivery systems
dc.titleSynthesis and transdermal permeation of novel N4-methoxypoly(ethylene glycol) carbamates of cytarabineen_US
dc.contributor.researchID12902608 - Legoabe, Lesetja Jan
dc.contributor.researchID10060510 - Du Preez, Jan Lourens
dc.contributor.researchID10065318 - Du Plessis, Jeanetta
dc.contributor.researchID10059768 - Breytenbach, Jaco Cornelius
dc.contributor.researchID20883072 - N'Da, David Dago

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