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Preparation and Evaluation of Amino Acid Based Salt Forms of Model Zwitterionic Drug Ciprofloxacin
Amr ElShaer; Defang Ouyang; Peter Hanson; Afzal R Mohammed
2013-01-30
Source PublicationJournal of Pharmaceutics & Drug Delivery Research
ISSN2325-9604
Volume2Issue:1Pages:1-10
Abstract

Ciprofloxacin (CIP) is a quinolone derivative which is widely used for the treatment of a number of urinary tract infections. It exhibits its antimicrobial activity by inhibiting bacterial DNA gyrase enzyme. BCS classification of CIP is challenging due to the absence of any linear dose proportionality of AUC in humans. Yet, most of the studies classify CIP as a BCS IV (low solubility & low permeability drug) candidate. This study aims at exploiting the zwitterionic nature of CIP and investigates the ability of acidic and basic amino acids to form new salts with the primary aim of improving its solubility. Two salts were prepared using L-glutamic acid and L-aspartic acid as counter ions which resulted in increasing CIP solubility by 2.9x103 and 2.5x103 folds respectively. On the other hand, cationic amino acids namely (L-arginine, L-lysine & L-histidine) failed to form any salts. To investigate the absence of salt formation with the cationic amino acids, the role of inter- and intra molecular interactions between CIP and amino acids on the salt formation was studied using molecular dynamic simulation. Both the experimental and theoretical results revealed that ionic and hydrophobic interactions are essential for salt formation and that the ionic interaction and/or hydrophilic interactions between CIP and amino acids molecules should be greater than hydrophobic interactions between CIP molecules. Future work will study the effect of the salts on the permeability behaviour of CIP across Caco-2 monolayers.
 

KeywordCiprofloxacin 1hnmr Ftir Simulation Studies Amino Acids
DOIhttps://doi.org/10.4172/2325-9604.1000111
Indexed By其他
Language英语
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Document TypeJournal article
CollectionInstitute of Chinese Medical Sciences
Corresponding AuthorAfzal R Mohammed
AffiliationAston Pharmacy School, Aston University, Birmingham B4 7ET, UK
Recommended Citation
GB/T 7714
Amr ElShaer,Defang Ouyang,Peter Hanson,et al. Preparation and Evaluation of Amino Acid Based Salt Forms of Model Zwitterionic Drug Ciprofloxacin[J]. Journal of Pharmaceutics & Drug Delivery Research,2013,2(1):1-10.
APA Amr ElShaer,Defang Ouyang,Peter Hanson,&Afzal R Mohammed.(2013).Preparation and Evaluation of Amino Acid Based Salt Forms of Model Zwitterionic Drug Ciprofloxacin.Journal of Pharmaceutics & Drug Delivery Research,2(1),1-10.
MLA Amr ElShaer,et al."Preparation and Evaluation of Amino Acid Based Salt Forms of Model Zwitterionic Drug Ciprofloxacin".Journal of Pharmaceutics & Drug Delivery Research 2.1(2013):1-10.
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