Ionization, lipophilicity and solubility properties of repaglinide

Journal of Pharmaceutical and Biomedical Analysis
Zoran Mandić, Vesna Gabelica

Abstract

Potentiometric and spectrophotometric titrations were used for the determination of ionization behaviour, lipophilicity and solubility profile of repaglinide. Acid-base equilibria were characterized by means of protonation macro- and microconstants using Target Factor Analysis of spectrophotometric data. Lipophilicity profiles were evaluated by determination of partition coefficients of neutral and ionized forms of repaglinide in biphasic octanol/water system. The intrinsic solubilities of repaglinide were determined from the solubility data and temperature dependence of intrinsic solubilities were evaluated using van't Hoff equation. Repaglinide possesses two protonation sites and in aqueous solutions exhibits ampholitic properties. At isoelectric pH the zwitterionic form of the molecule predominates over the uncharged form with the tautomeric ratio, logKz=1.9. The difference between calculated and measured logP values, as well as the difference between logP values of uncharged form of repaglinide, HR0, and either one of mono-charged forms indicated the significant partition of zwitterion into octanol. Temperature dependence of solubility data revealed exothermic dissolution process with DeltasolH=-36 kJmol-1 and negative entr...Continue Reading

Citations

Nov 20, 2013·Pharmaceutical Research·Luca SettimoRonald M A Knegtel
Apr 25, 2013·International Journal of Pharmaceutics·Yuan GaoJianjun Zhang
Jul 17, 2012·Journal of Medicinal Chemistry·Károly Mazák, Béla Noszál
Apr 12, 2008·Chemical Research in Toxicology·Gregor LutheGabriele Ludewig
Jun 19, 2013·AAPS PharmSciTech·N S Desai, M S Nagarsenker
Jun 1, 2014·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Károly Mazák, Béla Noszál
Nov 29, 2011·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Károly Mazák, Béla Noszál
Jul 6, 2011·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Károly MazákBéla Noszál
Jul 26, 2011·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Kristiina TerttiKari Laine
Oct 11, 2008·Chemical Biology & Drug Design·Neelam Seedher, Mamta Kanojia
Aug 16, 2013·CPT: Pharmacometrics & Systems Pharmacology·Hm Jones, K Rowland-Yeo
Apr 14, 2016·Journal of Pharmaceutical and Biomedical Analysis·Károly Mazák, Béla Noszál
Nov 19, 2015·Acta Pharmaceutica Sinica. B·Sandeep Kalepu, Vijaykumar Nekkanti
Jul 1, 2015·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Károly MazákBéla Noszál
Mar 12, 2015·European Journal of Pharmaceutics and Biopharmaceutics : Official Journal of Arbeitsgemeinschaft Für Pharmazeutische Verfahrenstechnik E.V·D SchönherrW Weitschies
Nov 23, 2016·Future Medicinal Chemistry·Zhiwei YangGang Yang
Jul 30, 2014·Journal of Solution Chemistry·Lidia ZapałaJan Kalembkiewicz
Mar 28, 2012·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Carolina SällAleksandra Galetin
May 21, 2020·ChemMedChem·Károly Mazák, Béla Noszál
Jun 13, 2009·Pharmaceutical Development and Technology·Neelam Seedher, Mamta Kanojia
Oct 19, 2019·Drug Development and Industrial Pharmacy·Shreya ThakkarManju Misra
Jan 10, 2012·Molecular and Cellular Biochemistry·Makula Chandra Sekhar, P Jaya Chandra Reddy
Nov 19, 2020·International Journal of Nanomedicine·Morteza YaghoobianSimin Dadashzadeh

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Chemical Reviews
Alessandra PagliaraBernard Testa
The Journal of Pharmacy and Pharmacology
P J Taylor, J M Cruickshank
© 2021 Meta ULC. All rights reserved