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1 Impact factor: 3.958/ICV: 4.10 ISSN: Pharma Science Monitor 8(3), Jul-Sep 2017 PHARMA SCIENCE MONITOR AN INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES Journal home page: STABILITY INDICATING HPTLC METHOD DEVELOPMENT AND VALIDATION FOR LURASIDONE Roshni B. Patel*, Zarna R. Dedania, S. M. Vijayendra Swamy Bhagwan Mahavir College of Pharmacy, BMEF Campus, Bharthana, Vesu, Surat ABSTRACT A stability indicating high performance thin layer chromatographic (HPTLC) method was developed for Lurasidone. The chromatography was performed on pre-coated silica gel 60F254 aluminium plate using the mobile phase ethyl acetate: toluene: chloroform (5:3:2, v/v/v) with UV detection at 254 nm. The method was demonstrated to be precise, accurate and specific with no interference from the tablet excipients and was able to separate the drug from the degradation products produced under acid, base, oxidative, thermal and photo degradation. The method was validated for linearity, accuracy, precision and specificity. The linearity of peak area responses was demonstrated within the concentration range of ng/spot with R 2 = The limits of detection and limits of quantitation were found to be ng/spot and ng/spot respectively. Precision result was found to be within the 2% RSD. The % Recovery of the drug was achieved in the range of % ± ± The method was applied for estimation of Lurasidone in solid oral tablet dosage forms and assay result was found to be 99.95% ± 0.57 %. Degradation of the drug in different condition like, Acid, Alkali, Oxidation, Thermal and Photolytic was found to be 48.96%, 72.19%, 30.21%, 24.86% and % respectively. It was found that alkaline stress condition is more susceptible to degradation. The results indicated that the proposed method can be used as a stability indicating method for estimation of Lurasidone. It was found that in Alkaline stress condition was for susceptible for degradation of Lurasidone. The validated Chromatographic method was further utilized to isolate the alkaline degradation product using preparative HPTLC technique and extensive FT-IR,ESI- MS/TOF and NMR studies were performed to ascertain the structure of degradant. The probable alkaline degradant was found to be (2-(piperazin 1 ylmethyl) cyclohexyl) methylamine. KEYWORDS: Lurasidone, HPTLC, Stability Indicating Method. INTRODUCTION Chemically Lurasidon is 1 [(3aR,4S,7R,7aS)-2-{(1R,2R)-2[4(1,2-benzisothiazol-3-yl) piperazin- 1 ylmethyl] cyclohexylmethyl} hexahydro-4,7- methano-2hisoindole-1, 3-dione)] show in fig.1. Lurasidone is a full antagonist at dopamine D2 and serotonin 5HT2A receptors, properties shared by most second-generation antipsychotics.
2 Impact factor: 3.958/ICV: 4.10 ISSN: Fig 1. Structure of Lurasidone The literature survey reveals that various methods for the determination of Lurasidone are reported. Among this UV spectrophotometric 2,3,4,5,6,7,8, HPTLC 9, RP-HPLC 10,11,12,13, stability indicating HPTLC methods 14,15,16 reported for Lurasidone. The stability indicating HPTLC for other antipsychotics are also reported. The aim of present study is to be developed and validate HPTLC method for Lurasidone and also to observe the degradation behaviour of Lurasidone under various stress condition to determine its Stability. To validate the developed analytical HPTLC method for Lurasidone according to ICH guidelines. To perform forced degradation study of Lurasidone under various stress conditions such as aqueous hydrolysis oxidatione, thermal stress and the photolytic conditions MATERIAL AND METHODS Materials HPTLC system Linomat V semi automatic sample applicator (Camag Linomat V, Muttenz, Switzerland).pure sample of Lurasidone was obtained for Enaltec leb Hyderabad, India. PREPARATION OF STANDARD SOLUTION Preparation of standard stock solution of Lurasidone Accurately weighed 100 mg of standard Lurasidone was transferred to 100 ml volumetric flask, dissolved in 25 ml methanol and diluted up to the mark with same to get stock solution having strength 1000 μg/ml. Preparation of calibration curve 0.5, 1, 1.5, 2, 2.5 and 3µl of standard stock solution of 1000 μg/ml of Lurasidone were spotted on pre-coated TLC plate under nitrogen stream using Linomat V semi automatic sample applicator. The plate was dried in the air and developed up to 80 mm using mixture of ethyl acetate : toluene : chlorofrom (5:3:2 v/v/v) as mobile phase in a twin trough chamber previously saturated with
3 Impact factor: 3.958/ICV: 4.10 ISSN: mobile phase for 30 minutes. The plate was removed from the chamber, dried in hot air oven and scanned and quantified at 254 nm in absorbance mode. The calibration curve was constructed by plotting area versus respective concentration (ng/spot). Preparation of mobile phase Pre coated silica gel aluminum plate 60F254 was washed with methanol and activated in oven at 60⁰C for 5 min. The standard stock solution of Lurasidone and degraded drug solutions were spotted separately on pre coated silica gel aluminum plate by using glass capillary tube and allowed to dry for few minutes. Different mobile phases (10 ml) were taken in 100 ml glass beaker and allowed to saturate for 30 minutes. The spotted plate was developed in mobile phase to about STABILLITY STUDY Forced degradation of Lurasidone was carried out under acidic, alkaline, oxidative, photolytic and dry heat conditions. Acidic degradation Accurately weighed 100 mg of Lurasidone was transferred to a 100 ml volumetric flask add 10 ml methanol. To the above solution 10 ml of 1M HCl was added. The solution was reflux for 2 hours at 60⁰C in water bath. After that cooled and neutralized by 1M NaOH and diluted up to mark with methanol. Alkaline degradation Accurately weighed 100 mg of Lurasidone was transferred to a 50 ml volumetric flask add 10 ml methanol. To the above solution 10 ml of 0.5M NaOH was added. The solution was reflux for 2 hours at 60⁰C in water bath. After that cooled and neutralized by 0.5N HCl and diluted up to mark with methanol. Oxidative degradation Accurately weighed 100 mg of Lurasidone was transferred to a 100 ml volumetric flask add 20 ml methanol. To the above solution add 5ml of 3% H2O2. The solution was reflux for 1 hour at 70⁰C in water bath. After that cooled and diluted up to mark with methanol. Photolytic degradation Accurately weighed 100 mg of Lurasidone was transferred to Petry plate with close lead. Plate was exposed to direct sunlight for 24 hrs. Add 20 ml methanol in petry plate and transfer it to 50 ml volumetric flask. Wash petry plate with small aliquots of methanol. Add it in volumetric flask and make up volume to 50 ml with methanol Thermal degradation (Dry heat degradation)
4 Impact factor: 3.958/ICV: 4.10 ISSN: Accurately weighed 100 mg of Lurasidone was transferred to Petry plate with close lead. Plate was heated in previously heated hot air oven at 800 C for 6 hrs. Remove petry plate and cooled it. Add 20 ml methanol petry plate and transfer it to 100 ml volumetric flask. Wash petry plate with small aliquots of methanol. Add it in volumetric flask and make up volume to 100 ml with methanol A volume of 3μl of each degraded solution was applied to TLC plate. The plate was dried in air and developed up to 80 mm using mixture of ethyl acetate : toluene: chlorofrom (5:3:2 v/v/v) as mobile phase in a Camag twin through chamber previously saturated with mobile phase for 30 minutes. The plate was removed from the chamber, dried in hot air oven and standard zones were scanned and quantified at 254 nm. METHOD VALIDATION The method was validated for its Liniarity range, accuracy, precision, Specificity, robustness. Method validation is carried out as per ICH guideline. Linearity and range The linearity was expressed in terms of correlation co-efficient of linear regression 5 analysis. The linearity range was determined by analysing 3 independent levels of calibration curve in the range of ng/spot for Lurasidone. A volume of 0.5, 1, 1.5, 2, 2.5, 3 µl of working standard solution (1000 µg/ml) were applied on TLC plate and analysed as per the proposed method. The calibration curve was prepared by plotting peak area vs. concentration and correlation coefficient was calculated. Specificity The spot of Lurasidone from dosage form were confirmed by comparing its Rf and absorbancereflectance spectrum with that of standard lurasidone. The peak purity of Lurasidone from each sample was determined by comparing the spectra scanned at peak start, peak apex, and peak end positions of the spot. Precision Repeatability of Measurement Standard stock solution of Lurasidone was spotted on a TLC plate, and analyzed by the proposed method. The obtained band was scanned seven times without changing plate position and percent RSD for measurement of peak area was calculated. Repeatability of Sample Application Standard solution 1000 ng/spot of Lurasidone was spotted on a TLC plate Six times, and analyzed by the proposed method. The area of seven spots was measured and percent RSD of peak area was calculated.
5 Impact factor: 3.958/ICV: 4.10 ISSN: Intra-Day and Inter-Day Precision Variation of the results within same day is called intra-day precision and variation of results amongst days is called inter-day precision. Intra-day precision and Inter-day precision of the proposed method was evaluated by analyzing the range of Lurasidone (1000, 1500 and 2000 ng/spot), three times on same day and three different days respectively. Accuracy Known amount of standard Lurasidone was added at 80%, 100% and 120% level to pre-analyzed sample of Lurasidone. The quantity of tablet powder equivalent to 40 mg of Lurasidone was transferred to four individual 100 ml volumetric flasks. Known amount of standard Lurasidone was spiked to pre-analyzed sample of Lurasidone according to table ml methanol was added to dissolve powder drug sample was made up to mark with methanol. A volume of 2 µl of all the solutions were spotted and analyzed. Limit of Detection Limit of detection was calculated using following equation as per ICH guidelines. LOD= 3.3 x SD/S Where SD is the standard deviation of the Y- intercepts of the five calibration curves and S is mean slope of the five calibration curves. Limit of Quantitation Limit of quantitation was calculated using following equation as per ICH guidelines. LOQ = 10 x SD/S Where SD is the standard deviation of the Y- intercepts of the five calibration curves and S is mean slope of the five calibration curves. Robustness By introducing small changes in the mobile phase composition, mobile phase volume and duration of chamber saturation time, the effects on the results were examined. Mobile phases having different compositions of ethyl acetate: toluene: chlorofrom 6:3:1 and 5:3:2 v/v/v) were tried and chromatograms were run. Mobile phase volume and duration of saturation were varied at 20±2ml (18, and 22 ml) and 20±10 min (10, and 30 min), respectively. Robustness of the method was studied in triplicate at a concentration level of 1000 ng/spot. Isolation and characterization of Alkali degradation of Lurasidone Accurately weighed 100 mg of Lurasidone was transferred to a 50 ml volumetric flask add 10 ml methanol. To the above solution 10 ml of 0.5M NaOH was added. The solution was reflux for 2 hours at 60⁰C in water bath. After that cooled and neutralized by 0.5N HCl and diluted up to
6 Impact factor: 3.958/ICV: 4.10 ISSN: mark with methanol. The alkaline degradation of the Lurasidone was confirmed by newly developed HPTLC method, where the major degradant formed in alkaline stressed condition was isolated through preparative HPTLC technique. FT-IR The FT-IR spectrum of Lurasidone s unknown degradant was recorded on the perkin Elmer model spectrum series FT-IR as pellets. Mass Spectroscopy The ESI spectrum of Lurasidone s unknown degradant was recorded on the Thermo scientific Mass Spectrophotometer. NMR The 1H NMR data for Lurasidone s unknown degradant was recorded in DMSO at 400 MHz on the FT NMR, Avance III, make Bruker. RESULT AND DISCUSSION OPTIMIZATION OF MOBILE PHASE The TLC procedure was optimized with a view to develop a stability indicating method to quantify the Lurasidone. Both the Lurasidone standard solutions and the degraded solutions prepared by forced degradation in different conditions were spotted on the TLC plates and were run in different solvents. Various mobile phases were tried are listed with inference in table 7.3. Finally mobile phase consisting Ethyl acetate: toluene: chlorofrom (5:3:2 v/v/v) showed good resolution with forced degradants and compact spot of Lurasidone was observed with R f value 0.64 ± This mobile phase was able to separate maximum the degradation products of Lurasidone in different stress conditions. Fig.2. Chromatogram of 3000 ng/spot of Lurasidone
7 Impact factor: 3.958/ICV: 4.10 ISSN: STABILITY STUDY ACID DEGRADATION After heating drug solution with 1M HCl at 60 C for 2 hr, the percentage degradation of Lurasidone in acidic condition was found to be 48.9 %. The chromatogram of acid treated Lurasidone showed additional peaks at R f = 0.60, Fig 3: Chromatogram of Lurasidone in acidic condition (3000 ng/spot) Degradation in Alkaline condition After heating drug solution with 1N NaOH at 60 C for 2 hr, the percentage degradation of Lurasidone in alkaline condition was found to be %.The chromatogram of alkali treated Lurasidone showed additional peaks at R f =0.48 and Fig. 4: Chromatogram of Lurasidone in basic condition (3000 ng/spot)
8 Impact factor: 3.958/ICV: 4.10 ISSN: Oxidative degradation After Refluxing drug solution with 5ml of 3 % hydrogen peroxide at 70 C for 1 hr, the percentage degradation of Lurasidone in oxidative condition was found to be %. The chromatogram of hydrogen peroxide treated Lurasidone showed one additional peak at R f = Fig.5: Chromatogram of Lurasidone in oxidative condition (3000 mg/spot) Photolytic degradation Drug sample was exposed to direct sunlight for 24 hr, the percentage degradation of Lurasidone in photolytic condition was found to be %. The chromatogram of direct sunlight treated Lurasidone showed additional peaks at R f = 0.29, 0.34,0.51). Fig. 6: Chromatogram Lurasidone in photolytic degradation study (3000 ng/spot) Thermal degradation Drug sample was exposed to dry heat 80 C for 6 hr in hot air oven, the percentage degradation of Lurasidone in thermal degradation was found to be %. The chromatogram of thermal degraded Lurasidone showed additional peaks at R f = 0.28, 0.68 and 0.75.
9 Impact factor: 3.958/ICV: 4.10 ISSN: Fig 7: Chromatogram of Lurasidone in thermal condition study TABLE 1: SUMMARY OF STABILITY STUDY Sr No. Force degradation condition 1 Acidic Condition 2 Alkaline condition 3 Oxidative Degradation 4 Photolytic Degradation 5 Dry heat Degradation Stress Lurasidone Rf value of % Condition remaining undergrad (%) degradants Degradation (1N , % HCl/60 C/2hrs) 0.75 (1N NaOH/60 C , % /2hr) 0.76 (3% v/v % H 2 O 2 /70 C/1hr) 80 C/6 hr , 0.34, % hours in , % sunlight 0.75 METHOD VALIDATION Linearity and range Linearity parameters for the Lurasidone peak area response versus the Lurasidone concentration were studied in the concentration range ng/spot.
10 Impact factor: 3.958/ICV: 4.10 ISSN: Fig 8. Chromatogram of 3000 ng/spot of Lurasidone TABLE 2: CALIBRATION CURVE DATA CONCENTRATION (ng/spot) PEAK AREA(Mean ± S.D.); (n=3) ± ± ± ± ± ± Area under curve (AU) y = 2.457x R² = Concentration (ng/spot) Fig 9: Calibration curve for Lurasidone ( ng/spot)
11 Impact factor: 3.958/ICV: 4.10 ISSN: LOD AND LOQ Detection limit and quantification limit was calculated by the method as described in Section and The signal-to-noise ratio of 3:1 and 10:1 were considered as LOD and LOQ and were found to be and ng/spot, respectively, which indicates the adequate sensitivity of the method. ACCURACY (% RECOVERY) The proposed method when used for extraction and subsequent estimation of Lurasidone from pharmaceutical dosage forms after spiking with 80,100 and 120% of additional drug afforded recovery of ± ± 0.99%. TABLE 3: RESULT OF ACCURACY (%RECOVERY) Level Amount from sample (mg) Amount Total Total Recovered % Recovery of Std. amount area amount (ng) Spiked (ng/spot) (Mea) SD (n=3) Lurasidone (mg) of spiked amount ± S.D (n=3) 0% % ± ± % ± ± % ± ± 0.73 PRECISION The data for intra-day and inter-day precision is presented in Table 7.9. The %RSD for peak area was found to be in the range of % and % for intraday and inter-day precision of Lurasidone respectively. TABLE 4: PRECISION Concentration (ng/spot) Intraday precision Interday precision ± ± ± ± ± ±
12 Impact factor: 3.958/ICV: 4.10 ISSN: ROBUSTNESS The % R.S.D. of the peak areas were calculated for change in mobile phase composition, mobile phase volume and chamber saturation time at a concentration level of 1000 ng/ spot in triplicate. The low values of % R.S.D. (<2) obtained after introducing small deliberate changes in the developed HPTLC method indicated the robustness of the method. The low value of % RSD indicated that the method is robust in the mentioned conditions. TABLE 5: SUMMARY OF VALIDATION PARAMETER Parameters Results Linearity range ng/spot Regression line equation y = 2.457x Correlation co-efficient(r2) Precision (%RSD) Repeatability of measurement (n=7) 1.18 Repeatability of sample application (n=7) 0.63 Intra-day precision (n=3) Inter-day precision (n=3) % Recovery(n=3) 99.81± ±0.99 Limit of Detection (LOD)(ng/spot) Limit of Quantitation (LOQ) (ng/spot) Specificity Specific ASSAY ANALYSIS The %Assay was found to be for 99.95% ± 0.57 Lurasidon. TABLE.6: Assay of tablet formulation Brand name of Label claim of Amount of % Label claim Tablet Tablet (mg) Lurasidone Obtained ±SD found (mg) (n=3) LUTADA 40mg ± ± 0.57 Isolation and characterization of Alkali degradation of Lurasidone The structure elucidation of isolated alkaline degradation product was carried out using IR, NMR and Mass spectral studies. The IR spectrum (KBr) of degradant was characterized by the absence
13 Impact factor: 3.958/ICV: 4.10 ISSN: of absorption frequency of C=O stretching which is present in standard Lurasidone spectrum at 1687 cm 1. Fig 10: Degradant FT-IR spectra for Lurasidone Alkali Degradant MASS Spectrum for Lurasidone The mass spectral data of Alkaline degradant Lurasidone characterized by the breaking of amide from the structure of Lurasidone confirms the appearance of base ion peak at m/z 205. Further the fragment was obtained at m/z 120. Fig 11: Alkali Degradant Mass spectra for Lurasidone
14 Impact factor: 3.958/ICV: 4.10 ISSN: Alkali Degradant NMR Spectrum for Lurasidon 1H NMR Data 1H NMR, 400 MHz, δ (ppm): 2.511(s, H of NH); (m, 2H of CH 2 ); 3.197(m, 2H of CH 2 ); 3.315(m, 2H, CH 2 ); 3.376(s, 2H, CH 2 ); 3.461(m, 2H, CH 2 ); 3.544(m, 2H, CH 2 ); 3.627(m, 2H, CH 2 ); 4.151(m, H, CH 2 ); 4.466(m, H, CH 2 ); 4.659(m, H, CH 2 ); 4.782(s, H, CH 2 ); 4.899(m, H, CH 2 ); 5.093(m, H, CH 2 NH 2 ); (d, 2H of NH 2 ). The δ (ppm) value between 3 to 4 is of cyclohexyl and between 4 to 5 of piperazine moiety. Fig 12: Alkali Degradant NMR spectra for Lurasidone The probable alkaline degradant from interpreting IR, NMR and Mass Spectral was found to be (2-(piperazin 1 ylmethyl) cyclohexyl) methylamine. CONCLUSION The proposed Stress testing HPTLC method provides simple, accurate and reproducible quantitative analysis for determination of Lurasidone without any interference from the related
15 Impact factor: 3.958/ICV: 4.10 ISSN: substances, impurities. The developed HPTLC method has advantages over other analytical methods due to many samples can be run simultaneously using a small quantity of mobile phase, thus minimizing analysis time and cost per analysis. REFERENCES 1. Chatwal GR., and Sham KA., Instrumental Methods of Chemical Analysis; 5th Edn; Himalaya Publishing House, 2011, pp Mali NP and Patel M, Development and Vallidated UV Spectrophotometric Method for estimation of Lurasidone in bulk and pharmaceutical dosage. Int. J. Res. Pharm and Sci. 2012, 2, Joshi NK and Dumashiya MN, Development and validation of Spectrophotometric method for estimation of Lurasidone hydrochloride: a novel antipsychotic drug in bulk and pharmaceutical dosage from. Int. J. Pharm. Sci. 2012, 3, Ishiyama T, Tokuda K and Ishibashi T Validated Spectrophotometric method for the estimation of Lurasidone and Pharmaceutical dosage from. Eur J Pharm. 2007, 572, Sudhir MS and Nadh RV, Simple and validated Ultraviolet Spectrophotometric method for the estimation of Lurasidone in bulk drug. Res. J. of pharmaceutical Bio and chem. Sci. 2013, 4, Muvvala SS and Ratankaram VN, Validated UV Spectrophotometric method for Quantitative analysis of Lurasidone hydrochloride in pharmaceutical dosage from. Res. J. of pharmaceutical Bio and chem. Sci. 2013, 4, Tadashi I and Tokuda K, Development and validation of spectrophotometric method for estimation of Lurasidone hydrochloride a novel antipsychotic drug in bulk and pharmaceutical dosage. Eur. J. of Pharm. 2010, Polwar AR and Damle MC. Development and validation UV spectrophotometric method for Estimation of Lurasidone in bulk and pharmaceutical formulation. Int. J. Res. Pharm. and chem. 2014, 4, Krunal JP and Satish P Method Development and validation for the estimation of Lurasidone by HPTLC. Int. J. Pharm.Drug. Ana. 2012, 2, Damodar K and Bhogineni S Development and validation RP-HPLC method for estimation of lurasidone in bulk pharmaceutical dosage form Drug. Inv. Tud. 2011; 3:
16 Impact factor: 3.958/ICV: 4.10 ISSN: Ishibashi T, Horisawa T, Tokuda K, Ishiyama T, Ogasa M and Tagashira R, Novel Analytical method Development and validation for the quantitative analysis of Lurasidone in Bulk and pharmaceutical dosage form by RP-HPLC. J Pharm. Exp The. 2010, 11, Kastani DS and Bala RJ. RP-HPLC Method development and validation for the Analysis of Lurasidone in pharmaceutical Dosage from. Drug inv.tod. 2013, Joshi NK and Shah NJ, Stability indicating RP-HPLC method for determination and validation of Lurasidone hydrochloride in bulk and pharmaceutical dosage from. Pharma sci. mon. 2012, 3, Chhabda PJ and Balaji M Development and Vallidation of Stabillity indicating HPTLC Method for quantification of Lurasidone dosage from by HPTLC, Int. J. Pharm. Res. Dev. 2013, Vadera N, Subramanian G, and Musmade P, Development and validation of Stabilityindicating method for determination of lurasidone in bulk drug and pharmaceutical dosage form by HPLC. J. Pharma. & Bio. Ana. 2006, 43, Dedania ZR and Sheth NR and Dedania RR, Stability indicating High-Performance Thin- Layer Chromatographic Determination of Quetiapine Fumarate. Int. J. Pharmaceu. Sci. Res.,2013,4(6):
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