European Journal of Chemistry 2011, 2(1), 36-46. doi:10.5155/eurjchem.2.1.36-46.371

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, Accepted: 21 Jan 2011, Published: 28 Mar 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.

2_1_36_46_800


Keywords


pKa, Potentiometry, Co-solvents, Lipophilicity, Spectrophotometry, HPLC

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.1.36-46.371

Article Metrics


This Abstract was viewed 1795 times | PDF Article downloaded 757 times

Citations

/


[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), 270, 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]. 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
/


[10]. 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
/


[11]. Yaşar Doğan Daldal, Ebru Çubuk Demiralay, Güleren Alsancak
Determination of spectrophotometric protonation constant of cholinesterase inhibitors
International Journal of Chemistry and Technology  1(1), 7, 2017
DOI: 10.32571/ijct.335934
/


[12]. 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
/


[13]. 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
/


[14]. 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
/


[15]. 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
/


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.


How to cite


Narasimham, L.; Barhate, V. Eur. J. Chem. 2011, 2(1), 36-46. doi:10.5155/eurjchem.2.1.36-46.371
Narasimham, L.; Barhate, V. Physico-chemical characterization of some beta blockers and anti-diabetic drugs - potentiometric and spectrophotometric pKa determination in different co-solvents. Eur. J. Chem. 2011, 2(1), 36-46. doi:10.5155/eurjchem.2.1.36-46.371
Narasimham, L., & Barhate, V. (2011). Physico-chemical characterization of some beta blockers and anti-diabetic drugs - potentiometric and spectrophotometric pKa determination in different co-solvents. European Journal of Chemistry, 2(1), 36-46. doi:10.5155/eurjchem.2.1.36-46.371
Narasimham, Lakshmi, & Vasant Dnyandeo Barhate. "Physico-chemical characterization of some beta blockers and anti-diabetic drugs - potentiometric and spectrophotometric pKa determination in different co-solvents." European Journal of Chemistry [Online], 2.1 (2011): 36-46. Web. 21 Sep. 2019
Narasimham, Lakshmi, AND Barhate, Vasant. "Physico-chemical characterization of some beta blockers and anti-diabetic drugs - potentiometric and spectrophotometric pKa determination in different co-solvents" European Journal of Chemistry [Online], Volume 2 Number 1 (28 March 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.1.36-46.371

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.