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Asian Journal of Chemistry; Vol Asian Journal of Chemistry; Vol. 26, No. 13 (2014), 3823-3826 ASIAN JOURNAL OF CHEMISTRY http://dx.doi.org/10.14233/ajchem.2014.15952 A Validated UV Spectroscopic Method for Simultaneous Determination of Benzil and Benzophenone Impurities in Phenytoin Sodium * POOJA KORDE and P.N. SANJAY PAI Department of Quality Assurance, Goa College of Pharmacy, Panaji-403 001, India *Corresponding author: E-mail: [email protected]; [email protected] Received: 24 June 2013; Accepted: 26 December 2013; Published online: 23 June 2014; AJC-15353 A simple, accurate, precise, economical and reproducible UV spectrophotometric method has been developed for the simultaneous determination of benzophenone and benzil impurities in phenytoin sodium. The method employs formation and solving of simultaneous equation using 222, 257 and 263 nm as the analytical wavelengths. Method was found to be precise and was reproducible as shown from the validation studies. Keywords: Benzil, Benzophenone, Phenytoin sodium, Simultaneous equation method. INTRODUCTION Benzophenone apart from being a raw material for synthesis of phenytoin sodium, is also reported to be a Phenytoin (5,5-diphenylimidazolidine-2,4-dione) is a degradant formed due to oxidative hydrolysis with potassium hydantoin antiepileptic used to control partial and generalized permanganate10. tonic-clonic seizures. It has also been used in treatment of Literature review revealed various HPLC methods11-13 for 1 trigeminal neuralgia and cardiac arrhythmias . the analysis of phenytoin sodium, but methods for analysis Benzophenone is used in the manufacture of hypnotic of its product related impurities could not be found in the 2 class of drugs and so it is considered as a potential impurity literature. British Pharmacopoeia (BP) specifies a TLC method 3-4 in phenytoin bulk powder and its dosage forms . Benzophe- to limit benzophenone in phenytoin3. United States Pharma- none is irritating to the eyes, the skin and the respiratory tract copoeia (USP) has recommended HPLC method for the deter- and at excessive exposure, CNS disturbance and coma may mination of benzophenone as main impurity in phenytoin4. A 2 5 6 be noted . Chhabra and Rhodes et al. have reported that liver polarographic and a derivative spectrophotometric method is a primary target organ of benzophenone toxicity in rats and have been used for the determination of benzophenone, as an mice. The toxicological profile of benzophenone is similar to impurity, in phenytoin14-15. However, no methods could be a number of known hepatocarcinogens, suggesting that benzo- found for the simultaneous determination of phenytoin along phenone is a potential liver carcinogen. The kidney was also with two of its potential impurities, benzophenone and benzil. identified as a target organ of benzophenone toxicity. Therefore, it was desirable to develop a simple and sensitive Phenytoin can also be synthesized by a base catalyzed simultaneous UV spectrophotometric method that could be addition of urea to benzil followed by a benzilic acid rearrange- applied in quality control laboratories for the simultaneous ment (1,2 phenyl migration) to form the desired product, determination of benzophenone and benzil as impurities, in known as the Biltz synthesis of phenytoin. Hence benzil is phenytoin drug samples. The proposed method is based on also considered as potential product related impurity in the formation and solving of simultaneous equation using 222, 7 phenytoin bulk powder . Benzil is irritating to eyes and skin 257 and 263 nm as the analytical wavelengths. on contact. Inhalation causes irritation of the lungs and respi- ratory system. Inflammation of the eye is characterized by EXPERIMENTAL redness, watering and itching. Skin inflammation is charac- terized by itching, scaling, reddening, or occasionally, blistering8. UV visible double beam spectrometer, Perkin Elmer 25 Repeated or prolonged exposure to benzil can produce target lambda with spectral bandwidth of 1 nm and a pair of matched organs damage9. quartz cells was used. 3824 Korde et al. Asian J. Chem. All the chemicals used were of analytical reagent grade 0.8 y = 0.063x + 0.045 and the solvents were of spectroscopic grade. Gift sample of 0.7 2 R = 0.997 phenytoin sodium was kindly provided by Goa Antibiotics 0.6 e c Private Limited, Tuem, Pernem Goa. Pure samples of benzo- n 0.5 a b phenone and benzil, methanol AR, sodium hydroxide and r 0.4 o s distilled water was used in the present study. b 0.3 A Solvent system: After assessing the solubility of compo- 0.2 nents in different solvents, a mixture of methanol, 0.1 N sodium 0.1 hydroxide and distilled water in the ratio of 4:3:3 was used as 0 solvent system for developing spectral characteristics. 0 5 10 15 Preparation of standard stock solution: Standard stock Concentration (µ g/mL) solution of benzophenone, benzil and phenytoin sodium was Fig. 3. Calibration curve of benzophenone at 257 nm prepared by dissolving 10 mg each, in 10 mL of solvent system 1.4 and final volume adjusted with same solvent. Working standard y = 0.105x + 0.222 1.2 solutions (100 µg/mL) were prepared by subsequent dilution R2 = 0.996 to 10 mL with same solvent system. 1.0 e c Construction of calibration graphs: Working standard n a 0.8 b r solutions of 10 µg/mL were prepared, heated on water bath o s 0.6 for about 1 h, cooled and scanned over the entire UV range b A 400-200 nm to obtain overlain absorption spectra (Fig. 1). 0.4 Wavelength of 222, 257 and 263 nm were selected as they are 0.2 λmax for phenytoin sodium, benzophenone and benzil, respec- 0 tively (Table-4). 0 5 10 15 Concentration (µ g/mL) 1.2 Fig. 4. Calibration curve of benzil at 263 nm 1.1 1.0 Benzil 263 nm The absorptivity values (A 1 %, 1 cm) were calculated at 0.9 the selected wavelengths for phenytoin sodium, benzophenone 0.8 and benzil. The concentration of each component was deter- 0.7 Benzophenone 257 nm mined by using simultaneous equation method. The concen- 0.6 tration of each component can be calculated using following 16 0.5 equation . 0.4 A1 = aX1 bcY + aY1 bcY + aZ1 bcZ (1) Phenytoin 22 nm 0.3 A2 = aX2 bcX + aY2bcY + aZ2 bcZ (2) 0.2 A3 = aX3bcX + aY3 bcY + aZ3bcZ (3) 0.1 A a( a – a a ) – a (A a – a A ) + a (A a – a A ) C = 1 Y2 Z3 Z2 Y3 Y1 2 z3 z2 3 1z 2 Y3 Y2 3 0 X (4) a X1 a( Y2a Z3 – a Z2a Y3 ) – a Y1 a( X2a z3 – a z2a X3 ) + a 1z a( X2a Y3 – a Y2a X3 ) 200 220 240 360 280 300 320 340 360 380 400 NM a (A a – a A ) – A (A a – a a ) + a a( A – A a ) C = X1 2 Z3 Z2 3 1 X2 z3 z2 X3 1z X2 3 2 X3 Fig. 1. Overlain spectra of phenytoin sodium, benzil and benzophenone Y (5) a X1 a( Y2a Z3 – a Z2a Y3 ) – a Y1 a( X2a z3 – a z2a X3 ) + a 1z a( X2a Y3 – a Y2a X3 ) a a( A – A a ) – a a( A – A a ) + A a( a – a a ) For linearity study, aliquots of standard solution were further C = X1 Y2 3 2 Y3 Y1 X2 3 2 X3 1 X2 Y3 Y2 X3 Z a a( a – a a ) – a a( a – a a ) + a a( a – a a ) (6) diluted with solvent system to get final working standard of X1 Y2 Z3 Z2 Y3 Y1 X2 z3 z2 X3 1z X2 Y3 Y2 X3 concentration ranging from 5-70, 1-10 and 1-10 µg/mL for where, A1, A2 and A3 are the absorbance values of the mixture phenytoin sodium, benzophenone and benzil, respectively at 222, 257 and 263 nm, respectively. aX1, aX2 and aX3 are the (Table-4). The calibration curves at their respective λmax were absorptivities of phenytoin at 222, 257 and 263 nm, respec- prepared from the absorbance values obtained (Figs. 2-4). tively. aY1, aY2 and aY3 are the absorptivities of benzophenone at 222, 257 and 263 nm, respectively. a , a and a are the 3.0 Z1 Z2 Z3 absorptivities of benzil at 222, 257 and 263 nm, respectively. 2.5 CX, CY and CZ are the concentration of phenytoin (x), e c 2.0 benzophenone (y) and benzil (z), respectively. n a b Application of the proposed method for the analysis r 1.5 o s y = 0.036x + 0.089 of benzophenone and benzil in phenytoin drug: Accurately b 1.0 A R2 = 0.998 measured aliquots of the suitable working standard solutions 0.5 of all the three compounds were transferred into a series of 0 10 mL volumetric flasks to prepare mixtures of benzophenone, 0 20 40 60 80 benzil and phenytoin sodium. The solutions were then diluted Concentration (µ g/mL) with solvent system to volume. Aliquots of suitable concen- Fig. 2. Calibration curve of phenytoin sodium at 222 nm trations were prepared and analyzed as described under Vol. 26, No. 13 (2014) Simultaneous Determination of Benzil and Benzophenone Impurities in Phenytoin Sodium 3825 construction of the calibration graphs. The concentration of accuracy was described by % recovery which was calculated benzophenone, benzil and phenytoin sodium was determined in the test solution using the simultaneous equation. using the simultaneous equation. The precision of the method (Table-1) was determined RESULTS AND DISCUSSION by analyzing six replicate mixtures of phenytoin (50 µg/mL) The proposed method developed for simultaneous analysis spiked with 1 µg/mL of impurity-1 (benzil) and impurity-2 of phenytoin sodium, benzil and benzophenone in mixture (benzophenone).
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