Login Register Cart 0
Generic placeholder image

Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Synthesis, Analytical Characterization and Spectroscopic Investigation of Chloramphenicol Impurity A for the Quality Control of Chloramphenicol and its Formulation as Per International Compendium

Author(s): Aparna Wadhwa, Faraat Ali*, Sana Parveen, Robin Kumar and Gyanendra N. Singh

Volume 17, Issue 5, 2020

Page: [382 - 388] Pages: 7

DOI: 10.2174/1570179417666200410170237

Price: $65

Abstract

Objective: The main aim of the present work is to synthesize chloramphenicol impurity A (CLRMIMP- A) in the purest form and its subsequent characterization by using a panel of sophisticated analytical techniques (LC-MS, DSC, TGA, NMR, FTIR, HPLC, and CHNS) to provide as a reference standard mentioned in most of the international compendiums, including IP, BP, USP, and EP. The present synthetic procedure has not been disclosed anywhere in the prior art.

Methods: A simple, cheaper, and new synthesis method was described for the preparation of CLRM-IMP-A. It was synthesized and characterized by FTIR, DSC, TGA, NMR (1H and 13C), LC-MS, CHNS, and HPLC.

Results: CLRM-IMP-A present in drugs and dosage form can alter the therapeutic effects and adverse reaction of a drug considerably, it is mandatory to have a precise method for the estimation of impurities to safeguard the public health. Under these circumstances, the presence of CLRM-IMP-A in chloramphenicol (CLRM) requires strict quality control to satisfy the specified regulatory limit. The synthetic impurity obtained was in the pure form to provide a certified reference standard or working standard to stakeholders with defined potency.

Conclusion: The present research describes a novel technique for the synthesis of pharmacopoeial impurity, which can help in checking/controlling the quality of the CLRM in the international markets.

Keywords: Chloramphenicol IMP A, degradation product, LC-MS, NMR, FTIR, DSC, HPLC.

« Previous Next »
Graphical Abstract

[1]
Roy, J. Pharmaceutical impurities-A mini-review. AAPS PharmSciTech, 2002, 3(2) E6
[http://dx.doi.org/10.1208/pt030206] [PMID: 12916943]
[2]
Bloom, N.N. Neurotransmission and the central nervous systemThe pharmacological basis of therapeutics, 9th ed; Hardman, J.G.; Limbird, L.E., Eds.; McGraw-Hill: New York, 2001, pp. 267-293.
[3]
Pilaniya, K.; Chandrawanshi, H.K.; Pilaniya, U.; Manchandani, P.; Jain, P.; Singh, N. Recent trends in the impurity profile of pharmaceuticals. J. Adv. Pharm. Technol. Res., 2010, 1(3), 302-310.
[http://dx.doi.org/10.4103/0110-5558.72422] [PMID: 22247862]
[4]
Federal Register. International Conferences on Harmonization 2000.
[5]
Tripathi, K.D. Essentials of Medical Pharmacology, 7th ed; Jaypee Brothers: New Delhi, 2013, pp. 1-1020.
[6]
Harmonized Tripartite Guideline, ICH Q3B (R3) Impurities in New Drug Products, November, 2003.
[7]
Harmonized Tripartite Guideline, ICH Q3C (R4) Impurities: Guidelines for residual solvents, November, 2016.
[8]
Harmonized Tripartite Guideline, ICH Q3A (R2) Impurities in New Drug Substances, October 2006.
[9]
Gupta, L.K. Spectroscopic characterization and quantitative determination of atorvastatin calcium impurities by novel HPLC method. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2012, 97, 495-501.
[http://dx.doi.org/10.1016/j.saa.2012.06.037] [PMID: 22842103]
[10]
Kaviyarasu, K.; Magdalane, C.M.; Anand, K.; Manikandan, E.; Maaza, M. Synthesis and characterization studies of MgO:CuO nanocrystals by wetchemical method. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2015, 142, 405-409.
[http://dx.doi.org/10.1016/j.saa.2015.01.111] [PMID: 25725447]
[11]
Gruhzit, O.M.; Fisken, R.A.; Reutner, T.F.; Martino, E. Chloramphenicol (chloromycetin), An antibiotic pharmacological and pathological studies in animals. J. Clin. Invest., 1949, 28(5 Pt 1), 943-952.
[http://dx.doi.org/10.1172/JCI102184] [PMID: 16695768]
[12]
Benford, D.; Ceccatelli, S.; Cottrill, B.; Di Novi, M.; Dogliotti, E.; Edler, L.; Farmer, P.; Fürst, P.; Hoogenboom, L.; Knutsen, H.K.; Lundebye, A-K.; Metzler, M.; Mutti, A.; Nebbia, C.S.; O’Keeffe, M.; Petersen, A.; Rietjens, I.; Schrenk, D.; Silano, V.; van Loveren, H.; Vleminckx, C.; Wester, P. Scientific Opinion on Chloramphenicol in food and feed. EFSA J., 2014, 12(11), 3907.
[13]
Sarmah, A.K.; Meyer, M.T.; Boxall, A.B. A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment. Chemosphere, 2006, 65(5), 725-759.
[http://dx.doi.org/10.1016/j.chemosphere.2006.03.026] [PMID: 16677683]
[14]
Balbi, H.J. Chloramphenicol: a review. Pediatr. Rev., 2004, 25(8), 284-288.
[http://dx.doi.org/10.1542/pir.25-8-284] [PMID: 15286274]
[15]
Jithan, A.V.; Mohan, C.K.; Vimaladevi, M. Development and evaluation of a chloramphenicol hypertonic ophthalmic solution. Indian J. Pharm. Sci., 2008, 70(1), 66-70.
[http://dx.doi.org/10.4103/0250-474X.40334] [PMID: 20390083]
[16]
Al-Rimawi, F. Analysis of chloramphenicol and its related compound 2-amino-1-(4-nitrophenyl) propane-1,3-diol by reversed-phase high performance liquid chromatography with UV detection. Chromatography. Res. Int., 2011, 6.
[17]
Le Belle, M.J.; Young, D.C.; Graham, K.C.; Wilson, W.L. High performance liquid chromatographic determination of chloramphenicol and 1-(4′-nitrophenyl)-2-aminopropane- 1,3-diol in pharmaceutical formulations. J. Chromatogr. A, 1979, 170, 282-287.
[http://dx.doi.org/10.1016/S0021-9673(00)84268-5]
[18]
Mildred, C.R.; Crooks, H.M.; John, C.; Quentin, R. Bartz.; Chloramphenicol (Chloromycetin). l IV.la Chemical Studies. J. Am. Chem. Soc., 1949, 71(7), 2458-2462.
[http://dx.doi.org/10.1021/ja01175a065]
[19]
Vigh, G.; Inczédy, J. Separation of some chloramphenicol intermediates by high-pressure liquid chromatography. J. Chromatogr. A, 1976, 116(2), 472-474.
[http://dx.doi.org/10.1016/S0021-9673(00)89921-5] [PMID: 1245584]
[20]
Wiese, B.; Martin, K.; Hermansson, J. Determination of chloramphenicol and its monosuccinate ester in piglet plasma using HPLC. Chromatographia, 1982, 15(12), 737-742.
[http://dx.doi.org/10.1007/BF02261367]
[21]
Boer, Y.; Pijnenburg, A. HPLC determination of chloramphenicol degradation in eye drops. Pharm. Weekbl. Sci., 1983, 5(3), 95-101.
[http://dx.doi.org/10.1007/BF01960984] [PMID: 6878004]
[22]
Seth, S.; Bannerjee, N.R. Estimation of chloramphenicol in presence of its degradation products. Indian J. Pharm. Sci., 1987, 49(2), 58-60.
[23]
Hong, L.; Altorfer, H. Determination of assay and impurities of gamma irradiated chloramphenicol in eye ointment. J. Pharm. Biomed. Anal., 2001, 24(4), 667-674.
[http://dx.doi.org/10.1016/S0731-7085(00)00460-X] [PMID: 11272324]
[24]
Bogusz, M.J.; Hassan, H.; Al-Enazi, E.; Ibrahim, Z.; Al-Tufail, M. Rapid determination of chloramphenicol and its glucuronide in food products by liquid chromatography-electrospray negative ionization tandem mass spectrometry. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2004, 807(2), 343-356.
[http://dx.doi.org/10.1016/j.jchromb.2004.04.027] [PMID: 15203049]
[25]
Ali, S.L. Separation and determination of the hydrolysis products of chloramphenicol in pharmaceutical preparations by high-performance liquid chromatography. J. Chromatogr. A, 1978, 154(1), 103-105.
[PMID: 670363]
[26]
Indian Pharmacopoeia 7th ed. 2014. pp. 2668-2669. Available at https:// www.pmda.go.jp/files/000214416.pdf
[27]
United States Pharmacopoeia. National Formulary 26; Rockville, MD: USA, 2008, 31. Available at https://www.who.int/medicines/areas/ quality_safety/ quality_assurance/resources/US_Pharmacopoeia.pdf?ua=1
[28]
Chinese Pharmacopoeia. 10th ed; 2015. Available at http://wp.chp.org.cn/ en/content.html?id=ff8080814fd5ba0a014fd6f0402c0143
[29]
The Japanese Pharmacopoeia. The ministry of health, labour and welfare, 17th ed; (JP17), 2015. Available at https://jpdb.nihs.go.jp/jp/index.aspx
[30]
British Pharmacopoeia. London, UK, 2007 Available at https://www. pharmacopoeia.com/the-british-pharmacopoeia
[31]
Long, A.G. Williams, R.L. United States Pharmacopoeia: National Formulary. Available athttps://www.who.int/medicines/areas/quality_safety/ quality_assurance/resources/US_Pharmacopoeia.pdf?ua=1
[32]
Silverstein, R.M.; Webster, F.X.; Kiemle, D.J. Spectrometric Identification of Organic Compounds, 7th ed; John Wiley and Sons, Inc.: New York, 2005.
[33]
Pavia, DL.; Lampmen, GM.; Kriz, G.S. Introduction to spectroscopy, 4th ed; Brooks Cole, 2008.

Rights & Permissions Print Cite
Article Metrics
9
1
© 2024 Bentham Science Publishers | Privacy Policy