Enantioselective determination of chlorpheniramine in various formulations by HPLC using carboxymethyl-β-cyclodextrin as a chiral additive

Abstract

A chiral mobile phase HPLC method is described for chiral separation and determination of chlorpheniramine (CP) enantiomers in various commercial preparations. Chromatographic separation was achieved on a conventional ODS column with a mixture of aqueous sodium phosphate (5 mM) containing 0.5 mM carboxymethyl-beta-cyclodextrin, methanol and triethylamine (73:25:2, v/v/v, pH 4.3) as the mobile phase. The flow rate of isocratic elution was 0.24 mL/min and peaks were detected at 224 nm. The method was applied to nine commercial CP preparations in six dosage forms and CP enantiomers were well separated without any disturbance of other ingredients or impurities present. The results showed that only one preparation was d-CP and the others were dl-CP preparations. The contents of all the preparations were found to be in the range of 97%-104% of labeled contents. This method was economical and convenient, affording sufficient accuracy, precision and reproducibility, as well as sensitivity and selectivity.

Enantioseparation of basic drugs by reverse phase high‐performance liquid chromatography system using carboxymethyl‐β‐cyclodextrin as chiral mobile phase additive

“…24,25 The primary attribute of β-CDs that allows them to affect diverse chiral substances is their chiral recognition ability to be easy-to-form inclusions with a range of sizes suitable for neutral or ionic guest molecules. 26,27 In addition, β-CDs can be modified to possess groups that will allow native β-CDs to have better aqueous solubility and therefore better chiral recognition ability than native β-CD, can be chemically modified to produce derivative neutral or anionic or cationic CDs, such as hydroxypropylβ-cyclodextrin (HP-β-CD), [28][29][30] sulfobutyl etherβ-cyclodextrin (SBE-β-CD), [31][32][33][34] and carboxymethylβ-cyclodextrin (CM-β-CD) [35][36][37] and others. 38 Moreover, the anionic β-CD derivatives have been widely explored in the separation of basic chiral compounds containing amino groups, due to the electrostatic interactions, besides the hydrophobic inclusions, which enhanced the stability of compounds-CD inclusions.…”

Synthesis of imprinted beads by aqueous suspension polymerisation for chiral recognition of antihistamines

“…CP and BP are antihistamine (H 1 -receptor antagonist) drugs often used as ingredients in 'over-the counter' treatments for the common cold and allergic conditions [12]. Both CP and BP bear chiral centres and exhibit enantioselectivity in their pharmacological responses [13]. The antihistaminic drugs are marketed as a racemic mixture.…”

Halogenation effects of pheniramines on the complexation with β-cyclodextrin

“…However, pharmacological activity of such compounds is attributed primarily to their S-enantiomers, which have been reported to exhibit higher plasma concentrations and a longer half-life than the R-enantiomers. S-enantiomers are approximately 100 times more potent than the R-enantiomers, while R-enantiomers are largely responsible for the sedative side effects of these drugs [4][5][6]. Thus, methods of separation to obtain singleenantiomer forms to improve the efficacy of the drug or suppress the side effects associated with the other enantiomer must be developed [1,7].…”