Literature DB >> 1975690

Site- and stereospecific ocular drug delivery by sequential enzymatic bioactivation.

N Bodor1, L Prokai.   

Abstract

Intraocular enzymes convert the ketoxime analogues of some beta-adrenergic blockers via a sequential bioactivation process involving hydrolysis to the corresponding ketones followed by reduction to the aryloxyaminoalcohols, which then exert known and predictable physiological and pharmacological effects only at the site of the action--i.e., in the eye--without any systemic side effects. The sequential nature of the process is highlighted by the observation that the administration of the ketone intermediate also leads to its conversion to the beta-adrenergic antagonist, the active compound. The reduction is stereospecific resulting in the formation of the more potent S-(-)-form of the drug, thus providing prospect to glaucoma treatment. The same activation process of the ketoximes does not take place systemically, thus administration of these ketoximes does not produce cardiovascular effects.

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Year:  1990        PMID: 1975690     DOI: 10.1023/a:1015863521513

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


  12 in total

Review 1.  Stereochemistry: a source of problems in medicinal chemistry.

Authors:  E J Ariëns
Journal:  Med Res Rev       Date:  1986 Oct-Dec       Impact factor: 12.944

2.  Enzymes of mercapturate synthesis and other drug-metabolizing reactions-specific localization in the eye.

Authors:  N D Das; H Shichi
Journal:  Exp Eye Res       Date:  1981-11       Impact factor: 3.467

3.  Stereoselective oxidative metabolism of propranolol in the microsomal fraction from rat and human liver. Use of deuterium labeling and pseudoracemic mixtures.

Authors:  W L Nelson; H U Shetty
Journal:  Drug Metab Dispos       Date:  1986 Jul-Aug       Impact factor: 3.922

4.  Optical isomers of propranolol.

Authors:  R Howe; R G Shanks
Journal:  Nature       Date:  1966-06-25       Impact factor: 49.962

5.  Stereoselective disposition and glucuronidation of propranolol in humans.

Authors:  B Silber; N H Holford; S Riegelman
Journal:  J Pharm Sci       Date:  1982-06       Impact factor: 3.534

6.  Oxidation of (R)- and (S)-propranolol in human and dog liver microsomes. Species differences in stereoselectivity.

Authors:  C von Bahr; J Hermansson; M Lind
Journal:  J Pharmacol Exp Ther       Date:  1982-08       Impact factor: 4.030

7.  Formation of adrenaline in the iris-ciliary body from adrenalone diesters.

Authors:  N Bodor; G Visor
Journal:  Exp Eye Res       Date:  1984-06       Impact factor: 3.467

8.  Stereoselective ring oxidation of propranolol in man.

Authors:  T Walle; U K Walle; M J Wilson; T C Fagan; T E Gaffney
Journal:  Br J Clin Pharmacol       Date:  1984-11       Impact factor: 4.335

9.  The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias.

Authors:  A M Barrett; V A Cullum
Journal:  Br J Pharmacol       Date:  1968-09       Impact factor: 8.739

10.  Improved delivery through biological membranes. 26. Design, synthesis, and pharmacological activity of a novel chemical delivery system for beta-adrenergic blocking agents.

Authors:  N Bodor; A ElKoussi; M Kano; T Nakamura
Journal:  J Med Chem       Date:  1988-01       Impact factor: 7.446

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  5 in total

Review 1.  Prodrug strategies in ocular drug delivery.

Authors:  Megha Barot; Mahuya Bagui; Mitan R Gokulgandhi; Ashim K Mitra
Journal:  Med Chem       Date:  2012-07       Impact factor: 2.745

Review 2.  Chemical delivery systems and soft drugs: Retrometabolic approaches of drug design.

Authors:  Yashumati Ratan Bhardwaj; Ashutosh Pareek; Vivek Jain; Dharma Kishore
Journal:  Saudi Pharm J       Date:  2013-05-09       Impact factor: 4.330

Review 3.  Ophthalmic drug design based on the metabolic activity of the eye: soft drugs and chemical delivery systems.

Authors:  Nicholas Bodor; Peter Buchwald
Journal:  AAPS J       Date:  2005-12-07       Impact factor: 4.009

Review 4.  Advances in the use of prodrugs for drug delivery to the eye.

Authors:  Pranjal Taskar; Akshaya Tatke; Soumyajit Majumdar
Journal:  Expert Opin Drug Deliv       Date:  2016-07-21       Impact factor: 6.648

5.  17β-Estradiol Delivered in Eye Drops: Evidence of Impact on Protein Networks and Associated Biological Processes in the Rat Retina through Quantitative Proteomics.

Authors:  Laszlo Prokai; Khadiza Zaman; Vien Nguyen; Katalin Prokai-Tatrai
Journal:  Pharmaceutics       Date:  2020-01-27       Impact factor: 6.321

  5 in total

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