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Current Pharmaceutical Analysis

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ISSN (Print): 1573-4129
ISSN (Online): 1875-676X

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Research Article

Determination of Epsilon Aminocaproic Acid Based on Charge Transfer Complexation with p-Nitrophenlol by Spectrophotometry

Author(s): Fang Tian and Sheng-Yun Li*

Volume 17, Issue 5, 2021

Published on: 11 February, 2020

Page: [603 - 608] Pages: 6

DOI: 10.2174/1573412916666200211104811

Price: $65

Abstract

Introduction: Spectrophotometry was investigated for the determination of epsilon aminocaproic acid (EACA) with p-nitrophenol (PNP). The method was based on Charge Transfer (CT) complexation of this drug as n-electron donor with π-acceptor PNP.

Methods: The experiment indicated that CT complexation was carried out at room temperature for 10 minutes in dimethyl sulfoxide solvent. The spectrum obtained for EACA/PNP system showed the maximum absorption band at a wavelength of 425 nm. The stoichiometry of the CT complex was found to be a 1:1 ratio by Job’s method between the donor and the acceptor. Different variables affecting the complexation were carefully studied and optimized. At the optimum reaction conditions, Beer’s law was obeyed in a concentration limit of 1～6 μg mL-1. The relative standard deviation was less than 2.9%. The apparent molar absorptivity was determined to be 1.86×104 L mol-1cm-1 at 425 nm. The CT complexation was also confirmed by both FTIR and 1H NMR measurements.

Results: The thermodynamic properties and reaction mechanism of the CT complexation have been discussed.

Conclusion: The developed method could be applied successfully for the determination of the studied compound in its pharmaceutical dosage forms with good precision and accuracy compared to the official method comprising t- and F-tests.

Keywords: Charge transfer complexation, epsilon aminocaproic acid, spectrophotometry, p-nitrophenol, FTIR, NMR.

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[1]
Siddiqui, M.R.; AlOthman, Z.A.; Rahman, N. Analytical techniques in pharmaceutical analysis: A review. Arab. J. Chem., 2017, 10, S1409-S1421.
[http://dx.doi.org/10.1016/j.arabjc.2013.04.016]
[2]
Alothman, Z.A.; Rahman, N.; Siddiqui, M.R. Review on pharmaceutical impurities, stability studies and degradation products: an analytical approach. Rev. Adv. Sci. Eng., 2013, 2, 155-166.
[http://dx.doi.org/10.1166/rase.2013.1039]
[3]
Rahman, N.; Azmi, S.N.H.; Wu, H.F. The importance of impurity analysis in pharmaceutical products: an integrated approach. Accredit. Qual. Assur., 2006, 11(1-2), 69-74.
[http://dx.doi.org/10.1007/s00769-006-0095-y]
[4]
Roy, D.K.; Saha, A.; Mukherjee, A.K. Spectroscopic and thermodynamic study of charge transfer complexes of cloxacillin sodium in aqueous ethanol medium. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2005, 61(9), 2017-2022.
[http://dx.doi.org/10.1016/j.saa.2004.08.001] [PMID: 15911386]
[5]
Rahman, N.; Sameen, S.; Kashif, M. Spectroscopic study of charge transfer complexation between doxepine and π-acceptors and its application in quantitative analysis. J. Mol. Liq., 2016, 222, 944-952.
[http://dx.doi.org/10.1016/j.molliq.2016.07.125]
[6]
The Pharmacopoeia of People’s Republic of China (Part II). Chinese medical science and technology press; Beijing, 2015, p. 1156.
[7]
Kalmadi, S.; Tiu, R.; Lowe, C.; Jin, T.; Kalaycio, M. Epsilon aminocaproic acid reduces transfusion requirements in patients with thrombocytopenic hemorrhage. Cancer, 2006, 107(1), 136-140.
[http://dx.doi.org/10.1002/cncr.21958] [PMID: 16708357]
[8]
Hobbs, J.C.; Welsby, I.J.; Green, C.L.; Dhakal, I.B.; Wellman, S.S. Epsilon aminocaproic acid to reduce blood loss and transfusion after total hip and total knee arthroplasty. J. Arthroplasty, 2018, 33(1), 55-60.
[http://dx.doi.org/10.1016/j.arth.2017.08.020] [PMID: 28939033]
[9]
Harper, R.A.; Sucher, M.G.; Giordani, M.; Nedopil, A.J. Topically applied epsilon aminocaproic acid reduces blood loss and length of hospital stay after total knee arthroplasty. Orthopedics, 2017, 40(6), e1044-e1049.
[http://dx.doi.org/10.3928/01477447-20170925-07] [PMID: 28968480]
[10]
Shi, F.W. CHEN, Z.Y.; LIU S. Effect of epsilon-aminocaproic acid on fibrinolysis in patients undergoing open heart surgery with cardiopulmonary bypass. Chin. J. Anesthesiol., 2005, 25(4), 255-257.
[11]
Thompson, M.E.; Saadeh, C.; Watkins, P.; Nagy, L.; Demke, J. Blood loss and transfusion requirements with epsilon-aminocaproic acid use during cranial vault reconstruction surgery. J. Clin. Anesth., 2017, 36, 153-157.
[http://dx.doi.org/10.1016/j.jclinane.2016.10.007] [PMID: 28183556]
[12]
Singh, S.; Annamalai, A. The efficacy of tranexamic acid versus epsilon amino caproic acid in decreasing blood loss in patients undergoing mitral valve replacement surger. Int. J. Anesthesia Clinical Med, 2017, 5(2), 11-18.
[http://dx.doi.org/10.11648/j.ja.20170502.12]
[13]
Viedma-Rodríguez, R.; Martínez-Hernández, M.G.; Flores-López, L.A.; Baiza-Gutman, L.A. Epsilon-aminocaproic acid prevents high glucose and insulin induced-invasiveness in MDA-MB-231 breast cancer cells, modulating the plasminogen activator system. Mol. Cell. Biochem., 2018, 437(1-2), 65-80.
[http://dx.doi.org/10.1007/s11010-017-3096-8] [PMID: 28612231]
[14]
Shepherd, J.A.; Nibbelink, D.W.; Stegink, L.D. Rapid chromatographic technique for the determination of epsilon-aminocaproic acid in physiological fluids. J. Chromatogr. A, 1973, 86(1), 173-177.
[http://dx.doi.org/10.1016/S0021-9673(01)81248-6] [PMID: 4765306]
[15]
Zhuang, W.J.; Mao, X.Y. Determination of aminocaproic acid in aminocaproic acid injection by HPLC. Anti. Infect. Pharm., 2016, 13(3), 506-510.
[16]
Keucher, T.R.; Solow, E.B.; Metaxas, J.; Campbell, R.L. Gas-chromatographic determination of an antifibrinolytic drug, epsilon-aminocaproic acid. Clin. Chem., 1976, 22(6), 806-809.
[http://dx.doi.org/10.1093/clinchem/22.6.806] [PMID: 1277465]
[17]
Adams, R.F.; Schmidt, G.J.; Vandemark, F.L. Determination of epsilon-aminocaproic acid in serum by reversed-phase chromatography with fluorescence detection. Clin. Chem., 1977, 23(7), 1226-1229.
[http://dx.doi.org/10.1093/clinchem/23.7.1226] [PMID: 872368]
[18]
Moorthy, G.S.; Stricker, P.A.; Zuppa, A.F. A simple and selective liquid chromatography-tandem mass spectrometry method for determination of ε-aminocaproic acid in human plasma. J. Appl. Bioana., 2015, 1(3), 99-107.
[http://dx.doi.org/10.17145/jab.15.016]
[19]
Sjoerdsma, A.; Arne, H. Determination of epsilon-aminocaproic acid in urine by means of high-voltage paper electrophoresis. Acta Chem. Scand., 1959, 13, 2150-2151.
[http://dx.doi.org/10.3891/acta.chem.scand.13-2150]
[20]
Pinto, P.C.A.G.; Saraiva, M.L.M.F.S.; Santos, J.L.M.; Lima, J.L.F.C. Fluorimetric determination of aminocaproic acid in pharmaceutical formulations using a sequential injection analysis system. Talanta, 2006, 68(3), 857-862.
[http://dx.doi.org/10.1016/j.talanta.2005.06.008] [PMID: 18970401]
[21]
Mulliken, R.S. Intensities of electronic transitions in molecular spectra II. charge-transfer spectra. J. Chem. Phys., 1939, 7, 20-33.
[http://dx.doi.org/10.1063/1.1750319]
[22]
Xuan, C.S.; Wang, Z.Y.; Song, J.L. Spectrophotometric determination of some antibacterial drugs using p-nitrophenol. Anal. Lett., 1998, 31(7), 1185-1195.
[http://dx.doi.org/10.1080/00032719808002855]
[23]
Khan, I.M.; Ahmad, A. Spectrophotometric and thermodynamic studies of charge transfer complexes of 8-hydroxyquinoline with π acceptor p-nitrophenol in different solvents. Mol. Cryst. Liq. Cryst. (Phila. Pa.), 2009, 515(1), 159-170.
[http://dx.doi.org/10.1080/15421400903290865]
[24]
Foster, R. Organic Charge-Transfer Complexes Academic Press:: London, 1969; p. 51. 387.
[25]
Saleh, G.A. Charge-transfer complexes of barbiturates and phenytoin. Talanta, 1998, 46(1), 111-121.
[http://dx.doi.org/10.1016/S0039-9140(97)00251-8] [PMID: 18967133]
[26]
Li, W.Y.; Chen, X.F.; Xuan, C.S. Study of fluorescence characteristics of the charge-transfer reaction of quinolone agents with bromanil. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2009, 71(5), 1769-1775.
[http://dx.doi.org/10.1016/j.saa.2008.06.045] [PMID: 18701342]
[27]
Benesi, H.A.; Hildebrand, J.H. A Spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc., 1949, 71(8), 2703-2707.
[http://dx.doi.org/10.1021/ja01176a030]
[28]
Person, W.B. Thermodynamic properties of donor-acceptor complexes. J. Am. Chem. Soc., 1962, 84(4), 536-540.
[http://dx.doi.org/10.1021/ja00863a007]

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