| Lipophilicity of zwitterions and related species: A new insight. | |
| | |
MedLine Citation:
|
PMID: 21726635 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
|
The experimental determination of microscopic partition coefficients for protonation isomers is elaborated for the first time, and applied for niflumic acid, an ampholytic, mainly zwitterionic drug for pains in joints and muscles. The acid-base microequilibria of niflumic acid are also characterized by NMR-pH and deductive methods using auxiliary compounds of reduced complexity. The results show that 16 times as many zwitterionic than non-charged microspecies exist in aqueous solution. Partition of the individual microspecies was mimicked by model compounds of the closest possible similarity, then correction factors were also determined and introduced. Thus the long-awaited intrinsic partition coefficients of the non-charged vs. zwitterionic species could be calculated. The non-charged microspecies is 390 times as lipophilic as its zwitterionic protonation isomer. The microscopic partition coefficients are also in line with the experimentally determined distribution coefficients. These results make evident that contribution of the zwitterionic microspecies to the overall lipophilicity is not negligible, especially at the isoelectric pH region of the compound. |
| | |
Authors:
|
Károly Mazák; József Kökösi; Béla Noszál |
Related Documents
:
|
22202875 - Metabolism of amino acids, dipeptides and tetrapeptides by lactobacillus sakei. 21744115 - Understanding the influence of phosphatidylcholine on the molecular weight of hyaluroni... 211975 - Effect of temperature on diauxic growth with glucose and organic acids in pseudomonas f... 21671055 - Evaluation of ethanol production from corncob using scheffersomyces (pichia) stipitis c... 8660285 - Retinoic acid modulation of glutathione and cysteine metabolism in chondrocytes. 10904935 - Antinutrients and digestibility (in vitro) of soaked, dehulled and germinated cowpeas. |
Publication Detail:
|
Type: JOURNAL ARTICLE Date: 2011-6-25 |
Journal Detail:
|
Title: European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences Volume: - ISSN: 1879-0720 ISO Abbreviation: - Publication Date: 2011 Jun |
Date Detail:
|
Created Date: 2011-7-5 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 9317982 Medline TA: Eur J Pharm Sci Country: - |
Other Details:
|
Languages: ENG Pagination: - Citation Subset: - |
Copyright Information:
|
Copyright © 2011. Published by Elsevier B.V. |
Affiliation:
|
Semmelweis University, Department of Pharmaceutical Chemistry, Research Group of Drugs of Abuse and Doping Agents, Hungarian Academy of Sciences, Hőgyes E. u. 9., H-1092 Budapest, Hungary. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Analysis of infant isolates of Bifidobacterium breve by comparative genome hybridization indicates t...
Next Document: Chemoembolization agents for cancer treatment.