Hydrolysis and Epimerization Kinetics of Pilocarpine in Aqueous Solution

Nunes, Mathews A.; Brochmann–Hanssen, E.

doi:10.1002/jps.2600630514

Cited by 50 publications

(8 citation statements)

References 9 publications

(10 reference statements)

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“…2-Phthalimidinoglutarimide and 2-phthalimidoadipinimide (derivatives of thalidomide) showed rapid racemization [52,53]. Nunes et al [54] described the epimerization reaction of pilocarpine (2S:3R) at C-2 chiral atom at pH 7.4 and 35°C with half life of 36 days. Pepper et al [55] reported in vitro racemization of 3-(4-aminophenyl)-pyrrolidine-2,5-dione (aromatase inhibitors), its N-pentyl analogue and antifungal econazoles (having benzylic protons) at pH 7.4 in phosphate buffer.…”

Section: In Vitro Racemizationmentioning

confidence: 98%

Homochiral Drug Design and Development by Racemization

Ali

2007

CCHTS

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One of the enantiomers of a racemic drug may be pharmacologically inactive or toxic or ballast and, hence, U.S. FDA and European agencies have issued certain guidelines for marketing of optically active (homochiral) drugs. However, some homochiral drug enantiomers racemize in to human body leading to the generation of other antipodes, which may be toxic or ballast to the human beings. In addition, racemization reduces the administrated dosage concentration when the optically active enantiomer is converted into its inactive form. Therefore, racemization studies of homochiral drugs are the important and urgent need of today. This article reviews in vitro and in vivo racemization of homochiral drugs. The racemization of some homochiral drugs is described considering the affect of different variables such as temperature, concentration of the drug, ionic concentration, pH, addition of cyclodextrins, formation of inclusion complexes, etc. Efforts have also been made to discuss the mechanisms of the racemization process. Attempts have been made to suggest safe dosages of such drugs.

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Section: In Vitro Racemizationmentioning

confidence: 98%

Homochiral Drug Design and Development by Racemization

Ali

2007

CCHTS

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“…2-Phthalimidinoglutarimide and 2-phthalimidoadipinimide (derivatives of thalidomide) showed a rapid racemization. 59,60 Nunes et al 61 described the epimerization reaction of pilocarpine (2S:3R) at C-2 chiral atom at pH 7.4 and 358C with half life of 36 days. Pepper et al 62 reported in vitro racemization of aromatase inhibitors i.e.…”

Section: In Vitro Racemizationmentioning

confidence: 99%

Role of racemization in optically active drugs development

et al. 2007

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U.S. Food and Drug Administration issues certain guidelines for marketing of optically active drugs as some enantiomers racemize into human body, leading to the generation of other antipodes, which may be toxic or ballast to the human beings. Moreover, racemization reduces the administrated dosage concentration as optically active enantiomer converted into its inactive counter part. Therefore, the study of racemization of such type of drugs is an important and urgent need of today. This article describes in vitro and in vivo racemization of optically active drugs. The racemization process of various optically active drugs has been discussed considering the effect of different variables i.e. pH, temperature, concentration of the drug, ionic concentration, etc. Attempts have also been made to discuss the mechanisms of racemization. Besides, efforts have been made to suggest the safe dosages of such type of drugs too.

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“…Pilocarpine, from the leaves of the Pilocarpus species, is a potent muscarinic agonist in use for the treatment of glaucoma. It does isomerizes under basic conditions to the inactive isopilocarpine [61]. Epibatidine has been isolated from frog skin (Epipedobates tricolour) and is a potent nicotinic receptor agonist, 200 times more active than morphine, and a very effective analgesic [62,63].…”

Section: Natural Products Active On the Nervous Systemmentioning

confidence: 99%