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Determination of Thiazinamium, Promazine and Promethazine in Pharmaceutical Formulations Using a CZE Method Francisco J

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Determination of Thiazinamium, Promazine and Promethazine in Pharmaceutical Formulations Using a CZE Method Francisco J Analytica Chimica Acta 535 (2005) 101–108 Determination of thiazinamium, promazine and promethazine in pharmaceutical formulations using a CZE method Francisco J. Lara, Ana M. Garc´ıa-Campana˜ ∗, Ferm´ın Ales-Barrero,´ Juan M. Bosque-Sendra Department of Analytical Chemistry, Faculty of Sciences, University of Granada, Avd. Fuente Nueva s/n, E-18071 Granada, Spain Received 26 July 2004; received in revised form 30 November 2004; accepted 30 November 2004 Available online 15 January 2005 Abstract We present the validation of a developed method using capillary zone electrophoresis (CZE) for quantitative analysis of three phenoth- iazines: thiazinamium methylsulphate (TMS), promazine hydrochloride (PMH) and promethazine hydrochloride (PTH) in pharmaceutical formulations. The influence of various parameters affecting the CZE separation (buffer pH and concentration, acetonitrile percentage, capil- lary temperature and applied voltage) was investigated by means of multivariate optimization using experimental designs so as to obtain the highest efficiency. The method allows the separation of the phenothiazines in 5.0 min at optimized conditions: 100 mM tris(hydroxymethyl)- aminomethane (Tris) buffer at a pH 8.0, 15% acetonitrile, capillary with 58.5 cm in length at 25 ◦C and a voltage of 30 kV.Detection occurred at 254 nm. Acceptable precision (relative standard deviation (R.S.D.) 5.3%) and linearity were achieved using the internal standard (IS) method. The limits of detection (LODs) were 2.8 ␮gml−1 for TMS and 3.3 ␮gml−1 for PMH and PTH. The method has been successfully applied in the analysis of pharmaceutical formulations. © 2004 Elsevier B.V. All rights reserved. Keywords: Capillary zone electrophoresis; Thiazinamium methylsulphate; Promazine; Promethazine; Pharmaceutical analysis 1. Introduction alkyl piperazine group, a piperidine moiety, or an aliphatic side chain containing an amino group. Capillary electrophoresis (CE) is a complementary ana- Thiazinamium methylsulphate (TMS) (10-[2-trimethyla- lytical technique to high performance liquid chromatogra- mmonium-propyl]-phenothiazine-methylsulphate), has anti- phy (HPLC). It presents, as main advantages, low reagent histaminic and anticholinergic properties. It is administered and sample consumption, high separation efficiency and re- by intramuscular injection to patients suffering from chronic duced analysis time. Despite these advantages, CE remains respiratory diseases. Few methods were developed for the less used in industrial routine analysis; it might be due to the determination of TMS, based on amperometric detection relative limited number of validated quantitative analytical [5], spectrophotometric detection [6], fluorescence quench- methods in CE [1–3]. ing [7], gas chromatography [8] or thin layer chromatography Phenothiazines are a group of basic drugs including a [9]. More recently, a validated method was established using phenothiazine ring with different substituents attached at reverse phase HPLC with UV detection for pharmaceutical the 2- and 10-position, which are used as antipsychotics, quality control [10]. Promazine hydrochloride (PMH) (10- neuroleptics and antihistamines [4]. The 10-substituent is an [3-dimethylamino-propyl]-phenothiazine), is a neuroleptic agent with strong anticholinergic, hypotensive and sedative effects. It is used mainly as an antipsychotic and antiemetic ∗ Corresponding author. Tel.: +34 958 248594; fax: +34 958 249510. agent and additionally as an adjunct agent in the management E-mail address: [email protected] (A.M. Garc´ıa-Campana).˜ of severe pain. It is administered in solutions for intramus- 0003-2670/$ – see front matter © 2004 Elsevier B.V. All rights reserved. doi:10.1016/j.aca.2004.11.081 102 F.J. Lara et al. / Analytica Chimica Acta 535 (2005) 101–108 cular injection. Promethazine hydrochloride (PTH) (10-[2- pKa values were also determined by CZE [34]. Until now, dimethylamino-propyl]-phenothiazine), is widely used as an only one CZE method has been published for the determi- antihistaminic for the symptomatic relief of hypersensitiv- nation of thioridazine and promethazine using as electrolyte ity reactions or for enhancing the analgesic, anesthetic and tris–acetic acid, pH 5.0, containing a fluorinated cationic sur- sedative effects of others drugs. It is usually used as coated factant to reverse the EOF [35]. tablets, creams or in liquid injections. In this paper, a new CZE method has been developed Promazine and promethazine were analyzed by many for the simultaneous analysis of thiazinamium methylsul- spectrophotometric methods using UV [11,12], fluorimetric phate, promethazine and promazine (Fig. 1) to be applied [13–15] and chemiluminescence detection [16,17]. in quality control of pharmaceutical preparations. Response Liquid [18–20] and gas chromatography [21] methods surface methodology has been applied to carry out a sys- were also used for their determination. Thin layer chromatog- tematic optimization. The present method has been validated raphy [22] and electrochemical methods [23,24] have been and complies with the ICH guidance requirements [36] for less used. industry. In the literature, CE has been rarely used for the study of phenothiazine derivatives. Promethazine and thioridazine were separated and detected in spiked urine by CZE with 2. Experimental end-column amperometric detection giving a detection limit − − in the 10 8 mol l 1 range [25]. Micellar electrokinetic chro- 2.1. Reagents and chemicals matography (MEKC) using a micellar citrate buffer pH 3.5 containing cyclodextrins was used for the separation of All chemicals and solvents were of analytical grade. Ace- thioridazine, trimeprazine, promethazine, ethopropazine and tonitrile (MeCN), methanol and sodium hydroxide were ob- methotrimeprazine [26]. Different studies were carried out tained from Panreac-Qu´ımica (Madrid, Spain). Hydrochlo- to establish the influence of different chiral selectors such as ric acid was purchased from Scharlaub (Barcelona, Spain). cyclodextrins [27–30] or proteins [31,32] and to study the Tris(hydroxymethyl)-aminomethane (Tris) was purchased influence of ␤-cyclodextrins [33] of structurally related phe- from Merck (Darmstadt, Germany). Thiazinamium methyl- nothiazines. The influence of pH on the electrophoretic be- sulphate and promethazine hydrochloride were obtained from havior of these structurally related phenothiazines and the Alfa Pharma (Belgium) and promazine hydrochloride was Fig. 1. Chemical structures of the studied phenothiazines. Promazine and promethazine are isomers. F.J. Lara et al. / Analytica Chimica Acta 535 (2005) 101–108 103 obtained from Federa (Belgium). Propylparaben, used as claim: 32.5 mg ml−1) were diluted up to 100 ml with wa- internal standard (IS) was purchased from Fluka (Stein- ter (260 ␮gml−1). An aliquot of 770 ␮l of this solution was heim, Germany). TMS ampoules were supplied by a hos- spiked with 500 ␮l of a propylparaben solution (1 mg ml−1) pital laboratory (Ghent, Belgium) and promethazine tablets diluting with deionized water to a final volume of 5 ml. Final (FRINOVA®) was purchased from local drugstore and are concentrations of 40 ␮gml−1 for TMS and 100 ␮gml−1 for produced by Rhone-Poulenc.ˆ PMH ampoules were prepared propylparaben were obtained. in our laboratory by mixing 50 mg of promazine hydrochlo- In the case of PMH ampoules, an aliquot of 200 ␮lwas ride, 3.6 mg sodium citrate, 0.75 mg citric acid and 1.0 mg diluted up to 10 ml, and 500 ␮l of this solution were spiked sodium formaldehyde sulphoxylate with 1 ml of water. with 1 ml of a propylparaben solution (1 mg ml−1) diluting − Deionized water (18.2 M cm 1) was prepared with a to 10 ml with deionized water to obtain a final concentration Milli-Q system (Millipore, Bedford, MA, USA). of 50 ␮gml−1 for PMH and 100 ␮gml−1 for propylparaben. A promethazine pill (label claim: 25 mg per unit) was 2.2. Instrumentation and CE procedures finely powdered and homogenized in a mortar, being dis- solved in an approximate volume of 70 ml with deionized CE experiments were carried out with a HP3D CE instru- water, sonicated for 15 min and filtered through a filter pa- ment (Agilent Technologies, Waldbron, Germany) equipped per. The filtrate was diluted with deionized water to a final with a diode-array detector. Data were colleted using the soft- volume of 100 ml. For CE analysis, 1 ml of this solution was ware provided with the HP ChemStation, version A.09.01. spiked with 500 ␮l of a propylparaben solution (1 mg ml−1) Analytes were monitored at 254 nm with a bandwidth of and completed with deionized water to a final volume of 30 nm. Separation was carried out in a silica fused capil- 5 ml, obtaining concentrations of 50 ␮gml−1 of PTH and lary 58.5 cm × 50 ␮m i.d. (effective length 50 cm) in normal 100 ␮gml−1 of propylparaben. mode, applying a voltage of 30 kV. For pH measurements, a pH meter (Crison model pH 2000, Barcelona, Spain) was employed. 2.4. Statistical software Samples injections were made in a hydrodynamic mode over 5 s under a pressure of 50 mbar. Optimized background For the estimation of the regression model and for the electrolyte solution was 100 mM tris aqueous solution ad- application of experimental designs in the multioptimiza- justed to pH 8.0 with hydrochloric acid and containing 15% tion procedure, STATGRAPHICS [37] was used. Peak purity (v/v) acetonitrile. When a new capillary was used, the cap- evaluation was carried out by CHEMSTATION [38] soft- illary was conditioned 20 min with 1 M NaOH solution, fol- ware. Data analysis was carried out by using the ALAMIN lowed by 30 min with deionized water. At the beginning of [39] software to estimate the performance characteristics. each day, the capillary was prewashed for 2 min with 0.1 M NaOH, 3 min with water and 7 min with running buffer. Af- ter each run, the capillary was postwashed for 1 min 0.1 M 3. Results and discussion NaOH, 4 min with deionized water and 3 min with buffer to maintain adequate reproducibility of run-to-run injections. 3.1. Optimization of experimental conditions 2.3.
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