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Physico-chemical characterization of some beta blockers and anti-diabetic drugs - potentiometric and spectrophotometric pKa determination in different co-solvents
Lakshmi Narasimham (1,*)
, Vasant Dnyandeo Barhate (2) (1) Department of Chemistry, Vivekanand Education Society’s College of Arts, Science and Commerce, Chembur, Mumbai, IN-400071, India
(2) Department of Chemistry, Vivekanand Education Society’s College of Arts, Science and Commerce, Chembur, Mumbai, IN-400071, India
(*) Corresponding Author
Received: 14 Dec 2010 | Revised: 21 Jan 2011 | Accepted: 21 Jan 2011 | Published: 28 Mar 2011 | Issue Date: March 2011
Abstract
In the present study we have determined the fundamental physico-chemical properties such as, ionization constant (pKa) and lipophilicity (log P) of some b-blockers and anti-diabetic drugs. The apparent ionization constant (psKa) of selected drugs were determined using potentiometric titration in various co solvent-water mixtures (methanol, ethanol, acetonitrile and dioxane) at different temperatures (25 to 45 °C) and ionic strengths (0.15 to 0.5 M). Effect of temperature, ionic strength and dielectric constant on dissociation constant has been compared. The aqueous pKa values were then obtained by Yasuda-Shedlovsky extrapolation. In the case of water-soluble drugs (Amiloride hydrochloride, metoprolol tartrate and propranolol hydrochloride), the extrapolated results were in good agreement with that of pKa values measured in aqueous solutions under the same experimental conditions, while for the water insoluble drugs (atenolol, amlodipine besylate, gliclazide, glipizide, glibenclamide and pioglitazone), the extrapolated results were in good agreement with the literature values. For few of the selected drugs, the psKa was determined spectrophotometrically and the results were compared with that of potentiometry in various co solvent mixtures. The measured log P values of selected drugs showed acceptable range to that of literature values.
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DOI: 10.5155/eurjchem.2.1.36-46.371
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[1]. Isabel B. Coutinho, Adilson Freitas, António L. Maçanita, J.C. Lima
Effect of water content on the acid–base equilibrium of cyanidin-3-glucoside
Food Chemistry 172, 476, 2015
DOI: 10.1016/j.foodchem.2014.09.060
[2]. Huiling Huo, Tingting Li, Lei Zhang
pKa determination of oxysophocarpine by reversed - phase high performance liquid chromatography
SpringerPlus 2(1), , 2013
DOI: 10.1186/2193-1801-2-270
[3]. Judith Amador-Hernandez, Alberto Rojas-Hernandez, Edith Madai Colunga-Urbina, Iliana Margarita De La Garza-Rodriguez, Miguel Velazquez-Manzanares, Luis Felipe Medina-Vallejo
New chemometric strategies in the spectrophotometric determination of pKa
European Journal of Chemistry 5(1), 1, 2014
DOI: 10.5155/eurjchem.5.1.1-5.901
[4]. Wei Li Lee, Peixin Wee, Chandra Nugraha, Say Chye Joachim Loo
Gastric-floating microcapsules provide controlled and sustained release of multiple cardiovascular drugs
J. Mater. Chem. B 1(8), 1090, 2013
DOI: 10.1039/C2TB00495J
[5]. D. Schönherr, U. Wollatz, D. Haznar-Garbacz, U. Hanke, K.J. Box, R. Taylor, R. Ruiz, S. Beato, D. Becker, W. Weitschies
Characterisation of selected active agents regarding pKa values, solubility concentrations and pH profiles by SiriusT3
European Journal of Pharmaceutics and Biopharmaceutics 92, 155, 2015
DOI: 10.1016/j.ejpb.2015.02.028
[6]. Mobina Alimohammady, Mansour Jahangiri, Farhoush Kiani, Hasan Tahermansouri
Molecular modeling, pK a and thermodynamic values of asthma drugs
Medicinal Chemistry Research 27(1), 95, 2018
DOI: 10.1007/s00044-017-2038-z
[7]. Ebru Çubuk Demiralay, Duygu Koç, Y. Doğan Daldal, Cansel Çakır
Determination of chromatographic and spectrophotometric dissociation constants of some beta lactam antibiotics
Journal of Pharmaceutical and Biomedical Analysis 71, 139, 2012
DOI: 10.1016/j.jpba.2012.06.023
[8]. Mehran Abbaszadeh Amirdehi, Mohammad Pousti, Farnaz Asayesh, Farrokh Gharib, Jesse Greener
Solvent Effects on Acid–Base Equilibria of Propranolol and Atenolol in Aqueous Solutions of Methanol: UV-Spectrophotometric Titration and Theory
Journal of Solution Chemistry 46(3), 720, 2017
DOI: 10.1007/s10953-017-0595-x
[9]. Y. Doğan Daldal, Ebru Çubuk Demiralay
Chromatographic and UV–visible spectrophotometric pKa determination of some purine antimetabolites
Journal of Molecular Liquids 317, 113930, 2020
DOI: 10.1016/j.molliq.2020.113930
[10]. Jarukorn Sripradite, Susannah A. Miller, Michael D. Johnson, Anan Tongraar, Debbie C. Crans
How Interfaces Affect the Acidity of the Anilinium Ion
Chemistry - A European Journal 22(11), 3873, 2016
DOI: 10.1002/chem.201504804
[11]. Imad I. Hamdan, Dina El-Sabawi, Rana Abu-Dahab
Solubility of Gliclazide and Ion-Molecular Interactions with Aminopropanol in Aqueous Solutions
Russian Journal of Physical Chemistry A 92(1), 84, 2018
DOI: 10.1134/S0036024418010107
[12]. Yaşar Doğan DALDAL, Ebru ÇUBUK DEMİRALAY, Güleren ALSANCAK
Determination of spectrophotometric protonation constant of cholinesterase inhibitors
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DOI: 10.32571/ijct.335934
[13]. Natalija Nakov, Jelena Acevska, Katerina Brezovska, Aneta Dimitrovska
Overview on chromatographic and potentiometric based approaches for pKa determination of sparingly soluble substances
Macedonian Pharmaceutical Bulletin 63(02), 21, 2018
DOI: 10.33320/maced.pharm.bull.2017.63.02.003
[14]. Tavakol Heidary Shayesteh, Moojan Radmehr, Farzad Khajavi, Reza Mahjub
Application of chemometrics in determination of the acid dissociation constants (pKa) of several benzodiazepine derivatives as poorly soluble drugs in the presence of ionic surfactants
European Journal of Pharmaceutical Sciences 69, 44, 2015
DOI: 10.1016/j.ejps.2014.12.013
[15]. Nadia Boceiri, Tayeb Benabdallah, Mohammed Hadj Youcef, Hasnia Reffas
Synthesis and Characterization of a Novel Series of Amphiphilic Mercapto-1,2,4-Triazole Schiff Base Ligands: Investigation of their Behavior in Hydro-Organic Solutions
Journal of Surfactants and Detergents 19(3), 583, 2016
DOI: 10.1007/s11743-016-1811-1
[16]. Slobodan M Jankovic
Pharmacokinetics of selective β1-adrenergic blocking agents: prescribing implications
Expert Opinion on Drug Metabolism & Toxicology 10(9), 1221, 2014
DOI: 10.1517/17425255.2014.937702
[17]. Natalija Nakov, Katerina Brezovska, Vasil Karchev, Jelena Acevska, Aneta Dimitrovska
Chromatographic and Surfactant Based Potentiometric Determination of Aqueous Dissociation Constant of Mupirocin
Current Analytical Chemistry 16(2), 158, 2020
DOI: 10.2174/1573411014666180704125016
[18]. Samar H. Thiab, Imad I. Hamdan, Dina El-Sabawi, Afaf H. Al-Nadaf
Effect of loratadine on the dissolution and bioavailability of gliclazide from its hydroxypropyl-β-cyclodextrin complex
Journal of Inclusion Phenomena and Macrocyclic Chemistry 85(3-4), 203, 2016
DOI: 10.1007/s10847-016-0620-5
[19]. Dilara Başat Dereli, Abbase Güleren Alsancak
Determination of the ionization constants of sulfonylureas in THF–water media by potentiometric titration and RPLC methods
Journal of the Iranian Chemical Society 19(5), 1889, 2022
DOI: 10.1007/s13738-021-02425-3
References
[1]. Albert, A. and Serjeant, E. P. A Laboratory Manual, 3rd edition, Chapman and Hall London. 1984.
[2]. Ramette R. W. J. Chem. Educ. 1967, 44, 647-654.
[3]. Serjeant E. P. John & Wiley and Sons, New York, 1984.
[4]. Qiang, Z.; Adams, C. Water Res. 2004, 38, 2874-2890.
doi:10.1016/j.watres.2004.03.017
PMid:15223282
[5]. Pool, S. K.; Patel, S.; Dehring, K.; Workman, H.; Pool, C. F. J. Chromatogr. A 2004, 1037, 445-454.
doi:10.1016/j.chroma.2004.02.087
PMid:15214681
[6]. Erdemgil, F. Z.; Sanli, S.; Sanli, N.; Ozkan, G.; Barbosa, J.; Guiteras, J.; Beltran, J. L. Talanta 2007, 72, 489-496.
doi:10.1016/j.talanta.2006.11.007
PMid:19071645
[7]. Evagelou, V.; Tsantili-Kakoulidou, A.; Koupparis, M. J. Pharm. Biomed. Anal. 2003, 31, 1119-1128.
doi:10.1016/S0731-7085(02)00653-2
[8]. Jimenez-Lozano, E.; Marques, I.; Barron, D.; Beltran, J. L.; Barbosa, J. Anal. Chim. Acta 2002, 464, 37-45.
[9]. Janos P. J. Chromatogr. A 2004, 1037, 15-28.
doi:10.1016/j.chroma.2003.11.101
[10]. Andrasi, M.; Buglyo, P.; Zekany, L.; Gaspar, A. J. Pharm. Biomed. Anal. 2007, 44, 1040-1047.
doi:10.1016/j.jpba.2007.04.024
PMid:17537608
[11]. Wrobel, R.; Chmurzynski, L. Anal. Chim. Acta 2000, 405, 303-308.
doi:10.1016/S0003-2670(99)00737-0
[12]. Meloun, M.; Havel, J.; Högfeldt, E. Computation of Solution Equilibria, Ellis Horwood, Chichester, 1988.
[13]. Ying-Sing, F.; Shiu-Fai, L. Analyst 1985, 110, 1439-1444.
doi:10.1039/an9851001439
PMid:4096389
[14]. Papanastasiou, G.; Ziogas, I. Talanta 1989, 36, 977-983 .
doi:10.1016/0039-9140(89)80178-X
[15]. Guillén, S. R.; Guzmán, C. M. Microchem. J. 1988, 37, 40-50 .
doi:10.1016/0026-265X(88)90165-8
[16]. Avdeef, A. Anal. Chim. Acta 1983, 148, 237-244.
doi:10.1016/S0003-2670(00)85168-5
[17]. Kin, T. Y.; Krisztina, T. N. Anal. Chim. Acta 2001, 434, 157-167.
doi:10.1016/S0003-2670(01)00810-8
[18]. Karl, B.; Christopher, B.; John, C.; Alan, H.; Ruth, A.; Derek, R. Anal. Chem. 2003, 75, 883-892.
doi:10.1021/ac020329y
PMid:12622380
[19]. Avdeef, A.; John, E. A. C.; Simon, J. T. Anal. Chem. 1993, 65, 42-49.
doi:10.1021/ac00049a010
[20]. Krisztina, T. N.; Karl, B.; Avdeef, A. Int. J. Pharm. 1997, 151, 235-248.
doi:10.1016/S0378-5173(97)04907-7
[21]. Avdeef, A.; Karl, J. B.; John, E. A. C.; Gilges, M.; Hadley, M.; Hibbert, C.; Patterson, W.; Tam, K. Y. J. Pharm. Biomed. Anal. 1999, 20, 631-641.
doi:10.1016/S0731-7085(98)00235-0
[22]. Gergely, V.; Rebeca, R.; Karl, B.; John, C.; Elisabeth, B.; Krisztina, T. N. Anal. Chim. Acta 2007, 583, 418–428.
doi:10.1016/j.aca.2006.10.015
PMid:17386575
[23]. Avdeef A. J. Pharm. Sci. 1993, 82, 183-190.
[24]. Kraft, A. J. Chem. Educ. 2003, 80, 554-559.
doi:10.1021/ed080p554
[25]. Avdeef, A.; Kearney, D. L.; Brown, J. A.; Chemotti Jr., A. R. Anal. Chem. 1982, 54, 2322–2326.
doi:10.1021/ac00250a041
[26]. Tam, K. Y.; Krisztina, T. N. Anal. Chim. Acta 2001, 434, 157-167.
doi:10.1016/S0003-2670(01)00810-8
[27]. Ruth, A.; Karl, B.; John, C.; Peake C.; Tam K. Y. J. Pharm. Biomed. Anal. 1998, 17, 699–712.
doi:10.1016/S0731-7085(98)00010-7
[28]. Krisztina, T. N.; Avdeef, A. J. Pharm. Biomed. Anal. 1996, 14, 1405–1413.
doi:10.1016/0731-7085(96)01773-6
[29]. Krisztina, T. N.; Avdeef, A.; Karl, B.; Podanyi, B.; Szasz, G. J. Pharm. Biomed. Anal. 1994, 12, 1369–1377.
doi:10.1016/0731-7085(94)00090-5
[30]. Wishart, D. S.; Knox, C.; Guo, A. C.; Cheng, D.; Shrivastava, S.; Tzur, D.; Gautam, B.; Hassanali, M.; DrugBank: Nucleic Acids Res. 2008, 36 (Database issue):D901-6.
[31]. Arnaud-neu, F.; Delgado, R.; Chaves, S. Pure Appl. Chem. 2003, 75, 71–102.
doi:10.1351/pac200375010071
[32]. Gutmann, V. Coord. Chem. Rev. 1976, 18, 225-255.
doi:10.1016/S0010-8545(00)82045-7
[33]. Loudon, G. M. Organic Chemistry, 4th edition, Oxford University Press, 2005.
[34]. Coetzee, J. F.; Padmanabhan, G. R. J. Amer. Chem. Soc. 1965, 87, 5005-5010.
doi:10.1021/ja00950a006
[35]. Avdeef A. Absorption and Drug Development. Solubility, Permeability and Charge State, Wiley & Sons, New Jersey, 2003.
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DOI Link: https://doi.org/10.5155/eurjchem.2.1.36-46.371
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