Vol-3, Issue-4, Suppl-2, Nov 2012 ISSN: Joshi et al PHARMA SCIENCE MONITOR

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1 PHARMA SCIENCE MONITOR AN INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES DEVELOPMENT AND VALIDATION OF RP-HPLC METHOD FOR ESTIMATION OF LURASIDONE HYDROCHLORIDE: A NOVEL ANTIPSYCHOTIC DRUG IN BULK AND PHARMACEUTICAL DOSAGE FORM Nirav K. Joshi*, Nehal J. Shah Department of Quality Assurance, Indubhai Patel College of Pharmacy and Research Center, Dharmaj, Dist. - Anand (Gujarat) ABSTRACT A Rapid, Simple, Specific, Accurate, Precise and Reproducible validated RP- HPLC method for the estimation of Lurasidone Hydrochloride in the Bulk and Pharmaceutical dosage form. RP-HPLC analysis was carried out using Acetonitrile: Methanol: Acetic Acid (30:45:25) mobile phase and Inertsil C18 ODS-3V column (250 mm x 4.6 mm, 5.0 ì particle size) as stationary phase with detection wavelength of 254 nm utilising Shimadzu HPLC (LC- 2010HT) equipped with UV-Visible Detector. Linearity was obtained in the concentration range of µg/ml for Lurasidone Hydrochloride. The retention time for Lurasidone Hydrochloride was 3.19 ± 0.11 minutes. The % recovery of the drug was found to be %. LOD and LOQ were found to be and μg/ml at 254 nm respectively for Lurasidone Hydrochloride. The method was found to be precise with RSD for intraday (n=3) and RSD for interday (n=3) for Lurasidone Hydrochloride Method was statistically validated for Accuracy, Precision, Specificity, LOQ, Robustness and Ruggedness according to ICH guidelines and can be used for routine analysis of Pharmaceutical dosage form. Keywords: Lurasidone Hydrochloride, Mobile Phase, RP-HPLC. INTRODUCTION Lurasidone is an atypical antipsychotic developed by Dainippon Sumitomo Pharma. It was approved by the U.S. Food and Drug Administration (FDA) for treatment of schizophrenia on October 28, Lurasidone Hydrochloride is not official in any Pharmacopoeia. Lurasidone Hydrochloride ( 3aR,4S,7R,7aS ) -{(1R,2R) 2 -[ 4 -( 1,2 - benzisothiazol -3-yl) piperazin 1 ylmethyl ] cyclohexylmethyl } hexahydro - 4, 7- methano -2 Hisoindole 1,3 - dione hydrochloride is a azapirone derivative antipsychotic used in the treatment of schizophrenia. IC Value

2 Figure 1 Structure of Lurasidone Hydrochloride Chemical Name : (3aR,4S,7R,7aS) 2 - {(1R,2R) 2 -[4 - (1,2 - benzisothiazol -3-yl) piperazin 1 ylmethyl] cyclohexylmethyl} hexahydro - 4, 7- methano -2 Hisoindole 1,3 - dione hydrochloride Molecular weight : : Lurasidone free base : Lurasidone Hydrochloride salt Pharmacology [4,5] : The mechanism of action of Lurasidone Hydrochloride, as with other drugs having efficacy in schizophrenia, is unknown. It has been suggested that the efficacy of Lurasidone Hydrochloride in schizophrenia is mediated through a combination of central dopamine Type 2 (D2) and serotonin Type 2 (5HT2A) receptor antagonism. And it give Antipsychotric Activity. Lurasidone may be useful for treating cognitive and memory deficits seen in schizophrenia for several reasons: 1) unlike many other antipsychotics, lurasidone does not block the muscarinic acetylcholine receptors, an action well-known to impair learning and memory; 2) lurasidone has prominent activity at 5-HT1A, 5-HT2A, 5-HT7, and α2cadrenergic receptors, all of which have been implicated in enhancement of cognitive function if modulated properly; 3) due to its low liability for extra pyramidal symptoms, lurasidone is unlikely to require co-administration of anticholinergics, which impair IC Value

3 cognition in their own right. In animal studies, lurasidone was found to be superior to all of the other antipsychotics examined in reversing dizocilpine induced learning and memory impairment,including risperidone, olanzapine, quetiapine, clozapine, aripiprazole, and haloperidol. Side effects are Leucopenia, Neutropenia, Tachycardia, Blurred vision, Decreased appetite, Rhabdomyolysis, Dysuria, Amenorrhea, Dysmenorrhea Side effects are generally similar to other antipsychotics. OBJECTIVE Survey of literature showed RP HPLC method for the estimation of Lurasidone Hydrochloride is not available in pharmaceutical preparations. Acetonitrile: Methanol: Acetic Acid (30:45:25) is used as a mobile phase. Attempt was made to develop RP- HPLC method for the estimation of Lurasidone Hydrochloride in bulk and Pharmaceutical Dosage Form. MATERIAL AND METHOD EXPERIMENTAL: Instrumentation: Chromatographic analysis was performed with a Shimadzu HPLC (LC-2010 HT) equipped with UV-Visible detector. Software LC Solution was used for LC peak integration along with data acquisition and data processing. The column used was Inertsil C18 column (250 x 4.6mm id, 5 µm particle size). Injector was Rhenodyne valve with 20μl fixed loop. Ultrasonic bath (Frontline FS 4 ultrasoniccleaner, Mumbai) was used for sonication for degassing of mobile phase. UV-1800, Shimadzu Corporation Ltd, Kyoto, Japan with UV Probe 2.32 software was used to obtain the overlay spectra of the drug to determine the analytical wavelength. Material: Lurasidone Hydrochloride API Marketed preparation:- Proprietary Name of Lurasidone Hydrochloride is Latuda and Manufactured by Sunavion Pharmaceutical Pvt.Ltd, U.S.A. IC Value

4 Each Tablet contains: Lurasidone Hydrochloride 40mg. Excipients q.s. Reagent: Acetonitrile (HPLC Grade) RFCL limited, NewDelhi. Acetic Acid (HPLC Grade) SD Fines chemicals, Bombay. Methanol (HPLC Grade) SD Fines chemicals, Bombay. Water (HPLC Grade) RFCL limited, NewDelhi. Method: Selection of detection wavelength The sensitivity of HPLC method that uses UV detection depends upon proper selection of detection wavelength. An ideal wavelength is the one that gives good response for the drug that is to be detected. In the present study drug solution of 10 µg/ml Lurasidone Hydrochloride was prepared in solvent mixtures of 30 ml Acetonitrile and 45 ml Methanol and 25 ml Acetic acid. This drug solution was than scanned in the UV region of nm and the overlain spectrum was recorded. Selection of chromatographic condition The drug selected for the present study are polar in nature and hence either reversed phase or ion-pair or ion-exchange chromatography can be used. Reversed phase HPLC was selected for the initial separations because of its simplicity and suitability. To optimize the chromatographic conditions, the effect of chromatographic variables such as mobile phase ph, flow rate, and solvent ratio were studied. The resulting chromatograms were recorded and the chromatographic parameters such as capacity factor, asymmetric factor, and resolution and column efficiency were calculated. The conditions that gave the best resolution, symmetry and capacity factor were selected for estimation. Effect of ratio of mobile phase The standard solution containing 40 µg/ml of Lurasidone Hydrochloride was chromatographed with mobile phase of 1) Acetonitrile: water (50:50% v/v) IC Value

5 2) Acetonitrile : Methanol (60:40 %v/v) 3) Acetonitrile : Water : Methanol (50:20:30 % v/v/v) 4) Acetonitrile: Methanol: Acetic Acid (50:30:20 %v/v/v) 5) Acetonitrile: Methanol: Acetic Acid (40:40:25 %v/v/v) 6) Acetonitrile: Methanol: Acetic Acid (30:40:30 %v/v/v) at a flow rate of 1.0 ml/min and the chromatograms were recorded. Estimation of Lurasidone Hydrochloride by RP-HPLC Method Preparation of mobile phase A mixture of 30 ml Acetonitrile, 45 ml Methanol and 25 ml Acetic Acid (30:45:25 v/v) filtered through 0.45 µm filter paper, sonicated for 10 minutes to degas the mixture and used as mobile phase. Preparation of standard stock solution Lurasidone Hydrochloride standard stock solution: (100 µg/ml) A 100 mg of standard Lurasidone Hydrochloride accurately was weighed and transferred to a 100 ml volumetric flask and dissolved in 10 ml Diluent. The flask was sonicated for 10 min. The flask was shaken and volume was made up to the mark with Diluent to give a solution containing 1000 µg/ml Lurasidone Hydrochloride. From this solution 10 ml was transfer to 100 ml volumetric flask. The volume was adjusted to the mark with the Diluent to give a solution containing 100 µg/ml Lurasidone Hydrochloride. Calibration curve for Lurasidone Hydrochloride: Calibration curve for the Lurasidone Hydrochloride (10-60 µg/ml): Appropriate volume of aliquot from standard Lurasidone Hydrochloride stock solution was transferred to same volumetric flask of 10 ml capacity. The volume was adjusted to the mark with Diluent to give a solution containing 10, 20, 30, 40, 50 and 60 µg/ml Lurasidone Hydrochloride. The standard solution was chromatographed for 5 minutes using mobile phase at a flow rate of 1.0 ml/min (Fig. 2, 3, 4, 5, 6 and 7). The graph was plotted for peak area vs. concentration for Lurasidone Hydrochloride. (Fig. 10) Determination of Lurasidone Hydrochloride from Tablet dosage form Sample preparation IC Value

6 Twenty tablets were weighed and finely powdered. The powder equivalent to 40 mg Lurasidone Hydrochloride was accurately weighed and transferred to volumetric flask of 100 ml capacity. 50 ml of diluent was transferred to volumetric flask and sonicated for 10 min. The flask was shaken and volume was made up to the mark with Diluent(400 µg/ml ). The above solution was filtered through whatmann filter paper (0.45µ). 1 ml of aliquot was taken and transferred to volumetric flask of 10 ml capacity and volume was made up to the mark with the Diluent. This solution was used for the estimation of Lurasidone Hydrochloride (40 µg/ml). Estimation of Lurasidone Hydrochloride in Tablet dosage form The prepared sample solution was chromatographed for 5 minutes using mobile phase at a flow rate of 1.0 ml/min (Fig.8). From the peak area obtained in the chromatogram, the amount of the drug was calculated. VALIDATION OF THE DEVELOPED HPLC METHOD: (1) Accuracy Accuracy is the closeness of the test results obtained by the method to the true value. To study the accuracy 20 tablets were weighed and powdered and analysis of the same was carried out. Recovery studies were carried out by addition of standard drug to the sample at 3 different concentration levels taking into consideration percentage purity of added bulk drug samples. (2) Precision The precision of an analytical method is the degree of agreement among individual test results when the method is applied repeatedly to multiple samplings of homogenous samples. It provides an indication of random error results and was expressed as coefficient of variation (RSD). (3) Repeatability Standard mixture solutions of Lurasidone Hydrochloride (10, 20, 30, 40, 50 and 60µg/ml) was prepared and chromatograms were recorded. Area was measured of the same concentration solution six times and RSD was calculated. (4) Intra and inter day precision IC Value

7 Variation of results within the same day (intra day), variation of results between days (inter day) were analyzed. Intraday precision was determined by analyzing Lurasidone Hydrochloride for three times in the same day. Inter day precision was determined by analyzing the drug daily for three days. (5) Reproducibility The areas were measured at different laboratory using another instrument by another analyst and the values obtained were evaluated using t-test to verify their reproducibility. (6) Linearity and Range The linearity of analytical method is its ability to elicit test results that are directly proportional to the concentration of analyte in sample within a given range. The range of analytical method is the interval between the upper and lower levels of analyte that have been demonstrated to be determined within a suitable level of precision, accuracy and linearity. (7) Specificity and selectivity Specificity is a procedure to detect quantitatively the analyte in presence of component that may be expected to be present in the sample matrix. While selectivity is the procedure to detect qualitatively the analyte in presence of components that may be expected to be present in the sample matrix. Commonly used excipients in Tablet preparation such as Soluble Starch, Lactose, Mg. Stearate were spiked in a pre weighed quantity of drug and then area was measured and calculations done to determine the quantity of the drug. (8) Ruggedness The solutions were prepared and then analyzed with change in the analytical conditions like different laboratory, different analyst, and different instrument. RESULTS AND DISCUSSION Chromatogram of standard solutions containing Different Concentration of Lurasidone Hydrochloride using Mobile Phase Acetonitrile: Methanol: Acetic Acid (30:45:25) IC Value

8 Vol-3, Issue-4, Suppl-2, Nov 2012 ISSN: Joshi et al 12 mau 254nm,4nm (1.00) mau 254nm,4nm (1.00) m in min FIGURE 2: 10 µg/ml Lurasidone Hcl FIGURE 3: 20 µg/ml Lurasidone Hcl 30.0 mau 254nm4nm (1.00) mau 254nm4nm (1.00) m in min FIGURE 4: 30 µg/ml Lurasidone Hcl FIGURE 5: 40 µg/ml Lurasidone Hcl mau 254nm4nm (1.00) 50 mau 254nm,4nm (1.00) m in min FIGURE 6: 50 µg/ml Lurasidone Hcl FIGURE 7: 60 µg/ml Lurasidone Hcl IC Value

9 1 3 2 Vol-3, Issue-4, Suppl-2, Nov 2012 ISSN: Joshi et al 40.0 m AU 254nm 4nm (1.00) m in FIGURE 8: Tablet formulation containing 40 µg/ml Lurasidone Hcl uv min FIGURE 9: Overlain Spectra of Lurasidone Hydrochloride in Methanol TABLE 1: RESULT OF CALIBRATION READINGS FOR LURASIDONE HYDROCHLORIDE IN MOBILE PHASE Concentrations Area (µg/ml) Mean ± S.D. (n=6) % RSD ± ± ± ± ± ± IC Value

10 FIGURE 10: Calibration curve of Lurasidone Hydrochloride by HPLC method TABLE 2: SYSTEM SUITABILITY TEST PARAMETER System Suitability Parameters Proposed Method Lurasidone Hydrochloride Retention times (R T ) (min) ± 0.11 Theoretical plates (N) Tailing factor (A S ) TABLE 3: STATISTICAL DATA FOR LURASIDONE HYDROCHLORIDE BY RP- HPLC METHOD Parameter Lurasidone Hydrochloride Linear Range(µg/ml) Slope Intercept Standard deviation of slope Standard deviation of intercept Limit of Detection (μg/ml) Limit of Quantitation (μg/ml) IC Value

11 TABLE 4 : DETERMINATION OF ACCURACY Spiking Amt of sample Amt. of drug added Amt. recovered % Recovery % Lurasidone Lurasidone Lurasidone Lurasidone Hydrochloride Hydrochloride Hydrochloride Hydrochloride (µg/ml) (µg/ml) (µg/ml) 80 % % % TABLE 5: PRECISION DATA FOR LURASIDONE HYDROCHLORIDE Conc. µg/ml Intra day (n=3) RSD Inter day (n=3) RSD ± ± ± ± ± ± TABLE 6: REPRODUCIBILITY DATA FOR LURASIDONE HYDROCHLORIDE (40 ΜG/ML) Instrument 1 Instrument 2 Result of t-test* Inference Area ± S.D (n=3) Area ± S.D (n=3) ± ± No significant difference * At 95% confidence interval, (t-tabulated = 4.30) TABLE 7: SPECIFICITY AND SELECTIVITY STUDY Study Specificity Selectivity Lurasidone Hydrochloride Specific Selective TABLE 8: SOLVENT SUITABILITY STUDY Time Area Result % Lurasidone Hydrochloride (40 μg/ml) Lurasidone Hydrochloride 0 hr ± hrs ± hrs ± hrs ± hrs ± IC Value

12 Factors ph of Mobile Phase Wavelength (nm) TABLE 9: ROBUSTNESS Retention time(min) Asymmetric Factor Min./nm/ml Lurasidone HCL 40 µg/ml Lurasidone HCL 40 µg/ml Mean± S.D ± ± Mean± S.D ± ±0.09 Flow Rate Mean± S.D ± ±0.08 TABLE 10: SUMMARY OF VALIDATION PARAMETERS OF RP-HPLC Parameters Lurasidone HCl Recovery % % Repeatability (RSD, n=6) Precision(RSD) Intra-day (n=3) Inter-day (n=3) Specificity Specific Solvent suitability Solvent suitable for 48 hrs TABLE 11: ASSAY RESULTS OF MARKETED FORMULATION Formulation Actual concentration µg/ml Lurasidone Hydrochloride Amount obtained µg/ml Lurasidone Hydrochloride % Lurasidone Hydrochloride Tablet ± ± IC Value

13 TABLE 12: OPTIMIZED CHROMATOGRAPHIC CONDITIONS FOR LURASIDONE HYDROCHLORIDE S. No Parameter Conditions 1. Mobile phase Acetonitrile : Methanol : Acetic Acid (30:45:25, % v/v/v) 2. Pump mode Isocratic 3. Stationary phase Column C 18, 250 x 4.6 mm, Particle size 5 µm 4. Flow rate (ml/min) Run time (min) Volume of Injection (μl) Detection wavelength (nm) Retention time (min) 3.19 ± Diluent Methanol CONCLUSION RP-HPLC method for estimation of Lurasidone Hydrochloride in Bulk and Pharmaceutical Dosage Form was developed and validated. The value of %RSD for intra-day and inter-day precision was found less than 2.This value confirms that method is precise. The value of % recovery greater than 98 % for this method shows that the method is accurate. The values of % recovery for analysis of formulations are found within the range. The observations and results obtained from this study including linearity, accuracy and precision (method precision as repeatability and intermediate precision as intra and inter day precision and ruggedness) are well within acceptable limit. From the experimental studies it was concluded that proposed method is sensitive, accurate and precise and can be adopted for the routine analysis of drug in Bulk and Pharmaceutical Dosage Form. ACKNOWLEDGEMENT First of All, I thank Almighty god choicest blessing and who has been the source of strength throughout my life. I humbly owe my gratitude and sincere regards to my mentor and esteemed guide Dr. Nehal J. Shah, Principal, Indubhai Patel College of Pharmacy and Research Centre, Dharmaj. IC Value

14 REFERENCES 1. Tadashi Ishibashi, Pharmacological Profile of Lurasidone, a Novel Antipsychotic Agent with Potent 5-HT7 and 5-HT1A Receptor Activity, JPET Fast Forward. April 19, Leslie Citrome Lurasidone for Schizophrenia: A Brief Review of a New Second-Generation Antipsychotic New York University School of Medicine, Department of Psychiatry, New York, December 13, Latuda (lurasidone HCl) was Associated with Low Rates of Weight Gain and Metabolic Changes in Patients with Schizophrenia in Data, 164th Meeting of the American Psychiatric Association. 4. Validation of Analytical Procedures: Methodology, ICH Harmonized Tripartite Guidelines, 1996, pp Quality Assurance of Pharmaceuticals, (A compendium of guidelines and related materials), 1997, Volume I, WHO, Geneva, pp Meltzer HY, Lurasidone in the treatment of schizophrenia: a randomized, double-blind, placebo- and olanzapine-controlled study., Department of Psychiatry, Vanderbilt University School of Medicine, Nashville, Tenn., USA., Latuda monograph,october 2011, 8. Kyeong-Ryoon Lee et al, Pharmacokinetics of Lurasidone, a novel atypical anti-psychotic drug in rats, Vol. 41, No. 12,2011, pp For Correspondence: Nirav Joshi niravjoshi1989@yahoo.com IC Value

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