Analysis of Orphenadrine Citrate in Various Chiral Stationary Phases: A Comparative Study

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Abstract

Background: Polysaccharide based chiral stationary phases (CSPs) were used to perform enantiomeric separation of Orphenadrine Citrate by Ultra-Fast Liquid Chromatography (UFLC) technique. Trials were conducted using the polar mode, reverse phase mode and normal phase mode. Amylose and Cellulose-based CSPs were used for the same.

Materials and Methods: Eight Amylose-based CSPs and four Cellulose-based CSPs were used in the reverse phase mode. Five Amylose-based CSPs and two Cellulose-based CSPs were used in polar mode. The only Cellulose-based CSP used in the normal phase mode could effectively separate Orphenadrine Citrate enantiomers with a good resolution.

Results and Discussion: Successful enantioseparation was obtained using Chiralcel OD-H containing Cellulose tris (3, 5- dimethylphenylcarbamate) as a chiral selector and n-hexane: Ethanol: Diethylamine (95: 05: 0.1, v/v/v) as the mobile phase. The developed method was validated in accordance with ICH guidelines (Q2R1).

Conclusion: The proposed objectives were successfully accomplished as the developed method could effectively resolve Orphenadrine Citrate enantiomers.

Keywords: Chiral stationary phase, enantioseparation, orphenadrine citrate, ultra-fast liquid chromatography, amylose-based CSPs, cellulose-based CSPs.

[1]
Tucker GT, Lennard MS. Enantiomer specific pharmacokinetics. Pharmacol Ther 1990; 45(3): 309-29.
[http://dx.doi.org/10.1016/0163-7258(90)90069-E] [PMID: 2405439]
[2]
Nation RL. Chirality in new drug development. Clinical pharmacokinetic considerations. Clin Pharmacokinet 1994; 27(4): 249-55.
[http://dx.doi.org/10.2165/00003088-199427040-00001] [PMID: 7834962]
[3]
Islam MR, Mahdi JG, Bowen ID. Pharmacological importance of stereochemical resolution of enantiomeric drugs. Drug Saf 1997; 17(3): 149-65.
[http://dx.doi.org/10.2165/00002018-199717030-00002] [PMID: 9306051]
[4]
Calcaterra A, D’Acquarica I. The market of chiral drugs: Chiral switches versus de novo enantiomerically pure compounds. J Pharm Biomed Anal 2018; 147: 323-40.
[http://dx.doi.org/10.1016/j.jpba.2017.07.008] [PMID: 28942107]
[5]
Tiritan ME, Ribeiro AR, Fernandes C, Pinto MM. Kirk-Othmer Encyclopedia of Chemical Technology; Sons, JW Pharmaceuticals, C, Ed; Wiley:. Hoboken, NJ, USA: Wiley 2016.
[6]
Aboul-Enein HY, Ali I. HPLC enantiomeric resolution of nebivolol on normal and reversed amylose based chiral phases. Pharmazie 2001; 56(3): 214-6.
[PMID: 11265585]
[7]
Ali I, Naim L, Ghanem A, Aboul-Enein HY. Chiral separations of piperidine-2,6-dione analogues on Chiralpak IA and Chiralpak IB columns by using HPLC. Talanta 2006; 69(4): 1013-7.
[http://dx.doi.org/10.1016/j.talanta.2005.12.004] [PMID: 18970673]
[8]
Ali I, Gaitonde VD, Aboul-Enein HY, Hussain A. Chiral separation of β-adrenergic blockers on CelluCoat column by HPLC. Talanta 2009; 78(2): 458-63.
[http://dx.doi.org/10.1016/j.talanta.2008.11.043] [PMID: 19203609]
[9]
Ali I, Saleem K, Hussain I, Gaitonde VD, Aboul‐Enein HY. Polysaccharides chiral stationary phases in liquid chromatography. Separ Purif Rev 2009; 38: 97-147.
[http://dx.doi.org/10.1080/15422110802589916]
[10]
Ali I, Gupta VK, Aboul-Enein HY, Singh P, Sharma B. Role of racemization in optically active drugs development. Chirality 2007; 19(6): 453-63.
[http://dx.doi.org/10.1002/chir.20397] [PMID: 17393472]
[11]
Ali I, Sanagi MM, Aboul-Enein HY. Advances in chiral separations by nonaqueous capillary electrophoresis in pharmaceutical and biomedical analysis. Electrophoresis 2014; 35(7): 926-36.
[http://dx.doi.org/10.1002/elps.201300222] [PMID: 23913555]
[12]
Ali I, Aboul-Enein HY. Impact of immobilized polysaccharide chiral stationary phases on enantiomeric separations. J Sep Sci 2006; 29(6): 762-9.
[http://dx.doi.org/10.1002/jssc.200500372] [PMID: 16830488]
[13]
Pharmaceutical Technology, Single-Enantiomer Drugs Poised for Further Market Growth, Sandra Erb 2016.
[14]
Ali I, Aboul-Enein HY. Enantioseparation of some clinically used drugs by HPLC using cellulose Tris (3,5-dichlorophenylcarbamate) chiral stationary phase. Biomed Chromatogr 2003; 17(2-3): 113-7.
[http://dx.doi.org/10.1002/bmc.220] [PMID: 12717799]
[15]
Aboul-Enein HY, Ali I. Comparative study of the enantiomeric resolution of chiral antifungal drugs econazole, miconazole and sulconazole by HPLC on various cellulose chiral columns in normal phase mode. J Pharm Biomed Anal 2002; 27(3-4): 441-6.
[http://dx.doi.org/10.1016/S0731-7085(01)00575-1] [PMID: 11755745]
[16]
Aboul-Enein HY, Ali I. Studies on the effect of alcohols on the chiral discrimination mechanisms of amylose stationary phase on the enantioseparation of nebivolol by HPLC. J Biochem Biophys Methods 2001; 48(2): 175-88.
[http://dx.doi.org/10.1016/S0165-022X(01)00148-8] [PMID: 11356487]
[17]
Aboul-Enein HY, Ali I. Optimization strategies for HPLC enantioseparation of racemic drugs using polysaccharides and macrocyclic glycopeptide antibiotic chiral stationary phases. Farmaco 2002; 57(7): 513-29.
[http://dx.doi.org/10.1016/S0014-827X(02)01242-9] [PMID: 12164206]
[18]
Al-Othman ZA, Al-Warthan A, Ali I. Advances in enantiomeric resolution on monolithic chiral stationary phases in liquid chromatography and electrochromatography. J Sep Sci 2014; 37(9-10): 1033-57.
[http://dx.doi.org/10.1002/jssc.201301326] [PMID: 24634395]
[19]
Srinivas NR, Barbhaiya RH, Midha KK. Enantiomeric drug development: issues, considerations, and regulatory requirements. J Pharm Sci 2001; 90(9): 1205-15.
[http://dx.doi.org/10.1002/jps.1074] [PMID: 11745774]
[20]
Chan SH, Lee W, Asmawi MZ, Tan SC. Chiral liquid chromatography-mass spectrometry (LC-MS/MS) method development for the detection of salbutamol in urine samples. J Chromatogr B Analyt Technol Biomed Life Sci 2016; 1025: 83-91.
[http://dx.doi.org/10.1016/j.jchromb.2016.05.015] [PMID: 27232053]
[21]
Li D, Leng A, Qi Y, et al. Simultaneous quantification of Schisandrin B enantiomers in rat plasma by chiral LC-MS/MS: Application in a stereoselective pharmacokinetic study. J Pharm Biomed Anal 2018; 159: 186-91.
[http://dx.doi.org/10.1016/j.jpba.2018.06.056] [PMID: 29990885]
[22]
Ali I, Al-Othman ZA, Al-Warthan A, Asnin L, Chudinov A. Advances in chiral separations of small peptides by capillary elec-trophoresis and chromatography. J Sep Sci 2014; 37(18): 2447-66.
[http://dx.doi.org/10.1002/jssc.201400587] [PMID: 25044566]
[23]
Aboul-Enein HY, Ali I. Comparison of the chiral resolution of econazole, miconazole, and sulconazole by HPLC using normal-phase amylose CSPs. Fresenius J Anal Chem 2001; 370(7): 951-5.
[http://dx.doi.org/10.1007/s002160100884] [PMID: 11569882]
[24]
Aboul-Enein HY, Ali I, Gübitz G, Simons C, Nicholls PJ. HPLC enantiomeric resolution of novel aromatase inhibitors on cellulose- and amylose-based chiral stationary phases under reversed phase mode. Chirality 2000; 12(10): 727-33.
[http://dx.doi.org/10.1002/1520-636X(2000)12:10<727:AID-CHIR5>3.0.CO;2-T] [PMID: 11054831]
[25]
Ali I, Al-Othman ZA, Hussain A, Saleem K, Aboul-Enein HY. Chiral separation of β-adrenergic blockers in human plasma by SPE-HPLC. Chromatographia 2011; 73: 251-6.
[http://dx.doi.org/10.1007/s10337-010-1891-4]
[26]
Ali I, Singh P, Aboul-Enein HY, Sharma B. Chiral analysis of ibuprofen residues in water and sediment. Anal Lett 2009; 42: 1747-60.
[http://dx.doi.org/10.1080/00032710903060768]
[27]
Saleh OA, El Behairy MF, Badawey AM, El Azzouny AA, Aboul Enein HY. Analysis of Stiripentol Enantiomers on Several Chiral Stationary Phases: A Comparative Study. Chromatographia 2015; 78: 267-71.
[http://dx.doi.org/10.1007/s10337-014-2818-2]
[28]
Kumar RS, Meyyanathan NS, Gowramma B. A Validated Chiral Liquid Chromatographic Method for the Enantiomeric Separation of Orphenadrine Citrate in Pharmaceutical Dosage Form. Curr Pharm Anal 2016; 12: 357-64.
[http://dx.doi.org/10.2174/1573412912666160128224822]