Literature DB >> 2235895

Enhanced delivery of zidovudine through rat and human skin via ester prodrugs.

T Seki1, T Kawaguchi, K Juni.   

Abstract

In an attempt to improve the skin delivery characteristics of Zidovudine (AZT, azidothymidine), five aliphatic esters (acetate, butyrate, hexanoate, octanoate, and decanoate) of AZT were synthesized and assessed as prodrugs of AZT. While the water solubility of the esters is lower than that of AZT, the solubilities in isopropylmyristate (IPM) and the partition coefficients (n-octanol:buffer) are higher. Susceptibility to enzymatic hydrolysis in the rat skin homogenate increases as the acyl chain of the ester is lengthened. Among the esters, acetate (C2-AZT) and hexanoate (C6-AZT) showed 2.4- and 4.8-fold enhanced permeation in human skin from an apolar vehicle (IPM) relative to application of AZT itself, respectively.

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Year:  1990        PMID： 2235895     DOI： 10.1023/a:1015902024664

Source DB:  PubMed          Journal:  Pharm Res        ISSN： 0724-8741            Impact factor:   4.200


  9 in total

1.  Effects of zidovudine in 365 consecutive patients with AIDS or AIDS-related complex.

Authors:  E Dournon; S Matheron; W Rozenbaum; S Gharakhanian; C Michon; P M Girard; C Perronne; D Salmon; P De Truchis; C Leport
Journal:  Lancet       Date:  1988-12-03       Impact factor: 79.321

2.  Effect of solvents on the permeation of nicardipine hydrochloride through the hairless rat skin.

Authors:  T Seki; K Sugibayashi; Y Morimoto
Journal:  Chem Pharm Bull (Tokyo)       Date:  1987-07       Impact factor: 1.645

3.  Zidovudine and bone marrow.

Authors:  N Mir; C Costello
Journal:  Lancet       Date:  1988-11-19       Impact factor: 79.321

4.  Effect of the absorption enhancer, Azone, on the transport of 5-fluorouracil across hairless rat skin.

Authors:  K Sugibayashi; K Hosoya; Y Morimoto; W I Higuchi
Journal:  J Pharm Pharmacol       Date:  1985-08       Impact factor: 3.765

5.  Estimation of blood concentration of drugs after topical application from in vitro skin permeation data. I. Prediction by convolution and confirmation by deconvolution.

Authors:  K Sato; T Oda; K Sugibayashi; Y Morimoto
Journal:  Chem Pharm Bull (Tokyo)       Date:  1988-06       Impact factor: 1.645

6.  Effects of vehicles and prodrug properties and their interactions on the delivery of 6-mercaptopurine through skin: bisacyloxymethyl-6-mercaptopurine prodrugs.

Authors:  R P Waranis; K B Sloan
Journal:  J Pharm Sci       Date:  1987-08       Impact factor: 3.534

7.  Plasma and cerebrospinal fluid pharmacokinetics of 3'-azido-3'-deoxythymidine: a novel pyrimidine analog with potential application for the treatment of patients with AIDS and related diseases.

Authors:  R W Klecker; J M Collins; R Yarchoan; R Thomas; J F Jenkins; S Broder; C E Myers
Journal:  Clin Pharmacol Ther       Date:  1987-04       Impact factor: 6.875

8.  3'-Azido-3'-deoxythymidine (BW A509U): an antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro.

Authors:  H Mitsuya; K J Weinhold; P A Furman; M H St Clair; S N Lehrman; R C Gallo; D Bolognesi; D W Barry; S Broder
Journal:  Proc Natl Acad Sci U S A       Date:  1985-10       Impact factor: 11.205

9.  Percutaneous absorption enhancer applied to membrane permeation-controlled transdermal delivery of nicardipine hydrochloride.

Authors:  T Seki; K Sugibayashi; K Juni; Y Morimoto
Journal:  Drug Des Deliv       Date:  1989-01
  9 in total
  8 in total

1.  Transdermal delivery of zidovudine (AZT): the effects of vehicles, enhancers, and polymer membranes on permeation across cadaver pig skin.

Authors:  Nuntakan Suwanpidokkul; Phensri Thongnopnua; Kaisri Umprayn
Journal:  AAPS PharmSciTech       Date:  2004-08-18       Impact factor: 3.246

2.  Topical iontophoresis of valaciclovir hydrochloride improves cutaneous aciclovir delivery.

Authors:  Nada Abla; Aarti Naik; Richard H Guy; Yogeshvar N Kalia
Journal:  Pharm Res       Date:  2006-08       Impact factor: 4.200

3.  Mechanism and site dependency of intestinal mucosal transport and metabolism of thymidine analogues.

Authors:  G B Park; A K Mitra
Journal:  Pharm Res       Date:  1992-03       Impact factor: 4.200

4.  Percutaneous absorption of 2',3'-dideoxyinosine in rats.

Authors:  E Mukherji; N J Millenbaugh; J L Au
Journal:  Pharm Res       Date:  1994-06       Impact factor: 4.200

5.  Analysis of in vitro skin permeation of 22-oxacalcitriol having a complicated metabolic pathway.

Authors:  Koji Yamaguchi; Tetsuya Mitsui; Toshinori Yamamoto; Rie Shiokawa; Yuko Nomiyama; Norihisa Ohishi; Yoshinori Aso; Kenji Sugibayashi
Journal:  Pharm Res       Date:  2006-03-25       Impact factor: 4.200

6.  Synthesis, structure-activity relationship and antiviral activity of 3'-N,N-dimethylamino-2',3'-dideoxythymidine and its prodrugs.

Authors:  Ramendra K Singh; Dipti Yadav; Diwakar Rai; Garima Kumari; C Pannecouque; Erik De Clercq
Journal:  Eur J Med Chem       Date:  2010-05-20       Impact factor: 6.514

7.  Enhancement of the transdermal delivery of zidovudine by pretreating the skin with two physical enhancers: microneedles and sonophoresis.

Authors:  Irene de Jesús Martínez-Segoviano; Adriana Ganem-Rondero
Journal:  Daru       Date:  2021-07-03       Impact factor: 4.088

8.  Synthesis, antibacterial and antiviral properties of curcumin bioconjugates bearing dipeptide, fatty acids and folic acid.

Authors:  Ramendra K Singh; Diwakar Rai; Dipti Yadav; A Bhargava; J Balzarini; E De Clercq
Journal:  Eur J Med Chem       Date:  2010-01-19       Impact factor: 6.514
  8 in total

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