(ACE) inhibitor class that is primarily used in cardiovascular. conditions. Lisinopril was introduced into therapy in the early
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1 107 CHAPTER 5 METHODDEVOLOPMENT FOR SIMULTANEOUS DETERMINATION OF LISINOPRIL AND HYDROCHLOROTHIAZIDE RELATED IMPURITIES IN LISINOPRIL AND HYDROCHLOROTHIAZIDE COMBINED TABLET DOSAGE FORMS USING HPLC
2 Introduction Pharmacologically Lisinopril is a Angiotension converting enzyme (ACE) inhibitor class that is primarily used in cardiovascular conditions. Lisinopril was introduced into therapy in the early 1990s.Lisinopril is chemically (S0)-[N 2 -[(S)-1-Carboxy-3-phenylpropyl]- L-lysyl]-L-proline dihydrate. Molecular formula is C 21 H 31 N 3 O 5 2H 2 O and structural formula is (1) (1) Hydrochlorothiazide, abbreviated HCTZ, HCT, or HZT, is a diuretic drug of the thiazide class. Hydrochlorothiazide is also used in combination with many popular drugs used to treat hypertension (2 to 5). Hydrochlorothiazide is chemically 6-chloro-3,4-dihydro-2H- 1,2,4-benzothiadiazine-7-sulphonamide1,1-dioxide. Molecular formula is C7H8ClN3O4S2 and structural formula is (2) (2)
3 109 The serious side effects of hypertension and renal failure associated with administration of higher doses of Lisinopril alone can be eliminated by the use of diuretic like hydrochlorothiazide in combination with Lisinopril. [1] So combined dosage form of Lisinopril and Hydrochloro thiazide is most useful combination drug (2, 3-5.) Aim and Literature Various analytical methods of HPLC [6, 7-9] and UV (10-11) and have been reported in literature for the assay of lisinopril and Hydrochlorothiazide singly and in combination. Lisinopril and Hydrochlorothiazide drug substances are official in USP [12-13) and EP (14-15). Lisinopril tablets and Hydrochlorothiazide Tablets are individually official in USP [16-17) and BP (18-19). However they are not selective for impurities in Lisinopril and hydrochlorothiazide combined formulations. Literature survey reveals that there is no reported method for the simultaneous determination of impurities of both these drugs from their combined tablet formulation. We attempted to develop a single method for simultaneous determination of all impurities in Lisinopril and Hydrochlorothiazide tablets. The developed method was validated. The structures of impurities of Lisinopril and Hydrochlorothiazide are serially given (3-11) (2RS)2-Amino-4- Phenyl Lisinopril-R,S,S- Isomer S,S,S- Diketo piperazine Butanoic Acid (3) (4) ( 5)
4 110 Cyclohexyl Analogue Salamide Chlorothiazide (7) (8) (9) 5-Chloro Hydrochlorothiazide Hydrochlorothiazide Dimer (10) (11) Lisinopril and Hydrochlorothiazide Related impurities 5.3. Experimental Materials and Equipment Lisinopril and Hydrochlorothiazide Tablets were manufactured by Aurobindo Pharma Ltd. Working standards and impurities were prepared by Chemical Research Department of Aurobindo Pharma Research Center. Acetonitrile, Methanol, Orthophosphoric acid, Triethylamine, 1-Hexane Sulphonic acid sodium salt were procured from Merck (India) Limited andpurified water USP was used. Reagents and solvents used were analytical or HPLC grade instruments used was same as given chapter-2. Column: Symmetry C18 (150 mm X 4.6 mm) 5µm particle size column HPLC Method(Developed) Mobile Phase Mobile Phase A: Hexane sulphonic acid buffer (ph 2.4): This was prepared by dissolving 1 g of sodium salt of Hexane sulphonicacid
5 111 in 1 litre of water, 5 ml triethyl amine was added. The ph was adjusted to 2.4 ± 0.1 with Orthophosphoric acid v/v. Mobile Phase B: Acetonitrile and methanol in the ratio of 90: Chromatographic Conditions flow rate was 1.5 ml/min. UV Detection was at 215 nm and column oven temperature was 50 C. Gradient pump mode was used. Time (Min) Mobile Phase A (v/v) Mobile Phase B (v/v) T T T T T Preparation Of Diluent Hexane sulphonic acid ph 3 buffer was used as diluents Preparation of System Suitability Stock Solution Weigh about 5 mg of chlorothiazide and about 3 mg of Lisinopril R-S-S-Isomer were transferred into a 50 ml volumetric flask, dissolved in 5 ml of methanol and made up to volume with methanol Preparation of System Suitability Solution
6 112 Accurately weighed quantities of about 45 mg of Lisinopril and 50 mg of Hydrochlorothiazide working standards were transferred into a 50 ml volumetric flask. 5 ml of methanol was added and sonicated to dissolve the drug. To this 2.5 ml of system suitability stock solution was added, mixed, made up to volume with diluent and then filtered. The above solution yielded a concentration of 5µg/ml of chlorothiazide, 3µg/ml of R.S.S isomer, 900µg/ml of Lisinopril and 1000µg/ml of Hydrochlorothiazide Preparation of Standard Solution Accurately weighed quantities of about 45 mg of Lisinopril and 50 mg of Hydrochlorothiazide working standards were transferred into a 100 ml clean, dry volumetric flask. 5mL of methanol was added, sonicated for 5 minutes to dissolve the drug and made upto volume with diluent. This solution was further serially diluted with diluent to obtain concentration of 4.5µg/ml of Lisinopril and 5µg/ml of Hydrochlorothiazide Preparation of Sample Solution A quantity of powder equivalent to about 50 mg of Hydrochlorothiazide was transferred to a 50 ml volumetric flask. 5 ml of methanol was added, the solution was sonicated for 15 minutes and made up to volume with diluent. The solution was centrifuged
7 113 and the supernatant was filtered.. (1000µg/ml of Hydrochlorothiazide and 800µg/ml of Lisinopril) Preparation of All Impurity mix solution The solutios each of 5 mcg/ml of impurities namely Salamide, Chlorothiazide, 2-Amino-4-Phenyl butanoic acid, 5 chlorohydrochlorothiazide, Lisinopril R,S,S isomer, Hydrochlorothiazide dimer, S,S,S Diketopiparazine, RSS diketopiperazine, cyclohexyl analogue were prepared Forced degradation studies for Specificity 5 M Sodium hydroxide, 5 M Hydrochloric acid and 30% Hydrogen peroxide solutions were used for forced degradation of Lisinopril and Hydrochlorothiazide tablets. Separately weighed and transferred tablets powder equivalent to about 50 mg of Hydrochlorothiazide into three different 50 ml volumetric flasks. To each flask 5ml of methanol was added and sonicated for 5minutes, 20 ml of diluent was added and sonicated for 15 minutes. For the first flask 5 ml of 5 M Hydrochloric acid was added and heated on water bath at 85 C for 15 minutes. For the second flask 5 ml of 5 M Sodium hydroxide was added and heated on water bath at 85 C for 30 minutes. For the third flask 5 ml of 30% Hydrogen peroxide was added and heated on water bath at 85 C for 30 minutes. All three flasks were cooled to room temperature, neutralized and made up to the mark with diluent.
8 114 The effect of light on the stability of Lisinopril and Hydrochlorothiazide was studied for tablets powder by exposing to low intensity UV lamp for 12,000 Lux/288 hours Test solutions for Linearity and Range 0.2 to 15 mcg/ml solutions of each of Lisinopriil, Hydrochlorothiazide and their related substances were used for studying the linearity and range of the method Preparation of Solutions for Testing Accuracy Sample solutions of Lisinopril and Hydrochlorothiazide and their impurities were prepared by transferring sample equivalent to about 50 mg of Hydrochlorothiazide and impurities,, in the range of 0.06 to 0.9 mg.final dilution was done using the diluent Solutions For Precision And Stability: Sample solutions of Lisinopril and Hydrochlorothiazide and their impurities were prepared by transferring sample equivalent to about 50 mg of Hydrochlorothiazide and impurities (0.20mg of each Lisinopril related impurities and 0.25 mg of each Hydrochlorothiazide impurities) into 50 ml volumetric flask.volume was made up to 50 ml with diluents Placebo Solution Placebo solution was prepared by an accurately weighed portion of the Placebo powder equivalent to 50 mg of Hydrochlorothiazide into a 50 ml volumetric flask. Added 5 ml of methanol and sonicated for 5 minutes. About 30 ml diluents was added and the flask was again sonicted for 15 minutes. The volume was made up to 50 ml with
9 115 diluents and the solution was centrifuged for 10 minutes at 5000 rpm. The supernatant was filtered. 5.4.Results and Discussions Method development and Optimization The method evaluation for determination of impurities was started using the monograph methods for individual drugs. The USP monograph method for Lisinopril tablets could not detect the Hydrochlorothiazide dimer impurity (Fig-5.1) Fig-5.1. Chromatogram of Lisinopril HCTZ tablets by USP method for Lisinopril tablets The EP monograph method for Hydrochlorothiazide drug substance could not detect the Lisinopril impurities(fig-5.2). Fig-5.2. Chromatogram of Lisinopril HCTZ tablets by the EP HCTZ method The monograph methods were also modified for its capability of simultaneous determination. Lisinopril and Hydrochlorothiazide had different PKa values (Lisinopril 3.3 and Hydrochlorothiazide 8.7)..Based upon the results obtained by our experimental trials we optimized the method. Some of critical parameters of optimization are as below.
10 116 Column: Optimized to Symmetry C 18, 5 µ ( mm) where in satisfactory baseline and separation was achieved. Mobile phase: The peak due to Hydrochlorothiazide was not retained irrespective of the change in the buffer and gradient programme. Hence introduction of ion pair reagent was required. The ph of mobile phase was optimized to 2.4 ± 0.1 for separation of all the impurities of Lisinopril and Hydrochlorothiazide. Maximum absorbance for Lisinopril was at 215 nm and for Hydrochlorothiazide was at 270 nm. At 215 nm, it was found that response of Lisinopril and Hydrochlorothiazide impurities was found to be satisfactory. So we have optimized nm as 215 nm. Optimized method was subjected to validation 5.3.FIG-LC Chromatogram of diluent by developed method 5.4.FIG-LC Chromatogram of System suit Method Validation Specificity All impurity solutions of Lisinopril and Hydrochlorothiazide were prepared and injected to conform the retention times. Sample solutions were prepared with and without spiking of impurities and injected into the HPLC.
11 117 The peak purity data of Lisinopril and Hydrochlorothiazide peaks in controle sample and spiked sample (known impurities spiked sample) indicated that the peaks are specific and are not co-eluting indicating specificity of the method. The data is presented in Table 5.1
12 FIG-LC Chromatogram of Placebo 5.6. FIG-LC Chromatogram of control sample 5.7. FIG-LC Chromatogram of spiked sample with all known impurities Table 5.1. Specificity-Peak purity results Name of the compound RT (min) RRT Purity angle Peak Purity Purity Threshold Salamide Chlorothiazide Hydrochlorothiazide * 0.286* 2-Amino-4-phenyl butanoic acid Chloro hydrochlorothiazide Lisinopril Lisinopril R,S,S-isomer Hydrochlorothiazide dimmer S,S,S-Diketopiperazine R,S,S-Diketopiperazine Cyclohexyl analogue RT - Retention Time RRT - Relative Retention Time * Obtained from Spiked sample (20+25mg / Tablet) - diluted
13 119 Further these samples were subjected to LC-MS (PE SCIEX-API 2000) analysis. Based on the observed m/z values (Salamide), (Chlorothiazide), (Hydrochlorothiazide), (2-Amino-4- phenyl butanoic acid), (5-Chloro hydrochlorothiazide), (Lisinopril), (Lisinopril R,S,S-isomer), (Hydrochlorothiazide dimer), (S,S,S-Dikdetopiperazine), (R,S,S-Dikdetopiperazine) and (Cyclohexyl analogue)the specificity of the method was confirmed. Lisinopril and Hydrochlorothiazide tablets and its placebo were subjected to stress conditions (Acid, Base, Peroxide, Thermal, Photolytic, Humidity degradations) and solutions were prepared with respective stressed samples. Each stressed sample was injected into the HPLC. From the placebo and diluent chromatogram, it was concluded that no peak was observed at the retention times of known impurities, Lisinopril and Hydrochlorothiazide peaks. Hence it can be concluded that no interference was found due to placebo also in the forced degraded samples it was observed that the sample purity angle is less than purity threshold. The data is presented in Table 5.2
14 120 Table 5.2. Forced degradation Degradation Mechanism Degradati on Condition % Area* % Degra dation Lisinopril Peak Purity Purity angle Purity thresh old Hydrochlorothiazide Peak Purity Purity angle Purity threshold - Un degraded M HCl Acid / 85 C 15 degradation min M NaOH Base / 85 C 30 degradation min % H Peroxide 2 O 2 / 85 C / degradation 30 min C / Thermal 288 degradation Hours ,000 Photolytic Lux / degradation Nil Hours 92% RH Hours Humidity / 25 C / degradation Nil * Sum of % Area of Hydrochlorothiazide and % Area of Lisinopril Limit of Detection (LOD) and Limit of Quantification (LOQ) The LOQ value for each impurity is well below the 50% of specification level, indicating that the method is sufficiently precise for the quantification of the Lisinopril and Hydrochlorothiazide impurities in Lisinopril and Hydrochlorothiazide tablets Linearity A series of solutions were prepared using Lisinopril and Hydrochlorothiazide working standards and their related substances
15 121 at concentration levels from Limit of Quantification (LOQ) to 150% of specification level and each solution was injected to the HPLC. The correlation coefficient is more than for Lisinopril, Hydrochlorothiazide and impurities of Lisinopril and Hydrochlorothiazide. Hence, the response of Lisinopril, Hydrochlorothiazide and each impurity are linear The LOD, LOQ and linearity data are presented in Table 5.3. Table 5.3 Linearity data of impurity salamide Conc. (µg/ml) Area Correlation Coefficient Slope Intercept Residual sum of squares 3193 Response Factor 0.81 Table 5.4 Linearity data of Impurity Chlorothiazide Concentration (µg/ml) Area Slope Intercept 263 Residual Sum of Squares 4523 Correlation Coefficient Response Factor 1.20
16 122 Table 5.5 Linearity data of Hydrochlorothiazide Concentration (µg/ml) Area Slope Intercept Residual Sum of Squares 7675 Correlation Coefficient Table 5.6 Linearity data of 2-Amino-4-phenyl butanoic acid Concentration (µg/ml) Area Slope Intercept 1356 Residual Sum of Squares 1578 Correlation Coefficient Table 5.7 Linearity data of 5-chloro Hydrochlorothiazide Concentration (µg/ml) Area Slope Intercept 1530 Residual Sum of squ ares 1882 Correlation Coefficient
17 123 \ Table 5.8 Linearity data of Lisinopril Concentration (µg/ml) Area Slope Intercept Residual Sum of Squares 1548 Correlation Coefficient Table Linearity data of impurity Lisinopril R,S,S-isomer Concentration (µg/ml) Area Slope Intercept 2440 Residual Sum of Squares Correlation Coefficient Response Factor Method Precision and Ruggedness Six sample solutions were prepared individually using same batch of Lisinopril and Hydrochlorothiazide tablets powder spiked with impurities at 0.5% level and each solution was injected to the HPLC. To check the ruggedness, separate set of six sample solutions with impurities spiked at 0.5% level was prepared by different analyst, on a different day, using different column and HPLC system. The data of precision and ruggedness is presented in Table 4 and Table 5. The %
18 124 RSD of all the impurities were well within 10%. Hence the method is precise and rugged. Table 5.10 Precision results Lisinopril (20mg) + Hydrochlorothiazide (25mg) Strength Name of the compound S1 S2 S3 S4 S5 S6 Mean SD % RS D 95% Confidenc e Interval Salamide ± Chlorothiazi de 2-Amino-4- phenyl butanoic acid 5-Chloro hydrochlorot hiazide Lisinopril R,S,S-isomer Hydrochlorot hiade dimer ± ± ± ± ± S,S,S- Diketopipera zine R,S,S- Diketopipera zine Cyclohexyl analogue ± ± ± 0.021
19 125 Table 5.11 Ruggedness results Name of the compound Salamide Chlorothiazi de 2-Amino-4- phenyl butanoic acid 5-Chloro hydrochloro thiazide Lisinopril R,S,Sisomer Hydrochloro thiade dimer S,S,S- Diketopiper azine R,S,S- Diketopiper azine Cyclohexyl analogue Lisinopril (20mg) + Hydrochlorothiazide (25mg) Strength S1 S2 S3 S4 S5 S6 Mean SD % RS D 95% Confidenc e Interval ± ± ± ± ± ± ± ± ± Accuracy Accuracy of the method was established by injecting solutions pflisinopril and Hydrochlorothiazide Tablets powder spiked with impurities at levels 50%, 100% and 150% of specification level in triplicate.. Data is presented in the table 6. The recovery results are within %. Hence the developed method has an acceptable level of accuracy Robustness
20 126 System suitability solution and sample solution spiked with impurities at 0.5% level was prepared and injected to the HPLC at different variable conditions (Change of flow ± 10%, wavelength±5nm, ratio of Acetonitril : Methanol in mobile phase B ± 2%, column oven temperature 45 C to 55 C and buffer ph ± 0.2 and 0.1).From the data of analysis of system suitability solution and sample solution at above mentioned conditions, it was found that there is no effect on the Relative Retention Times of impurities in the system suitability solution. The resolution of all the impurities at the deliberately varied conditions was also not altered. However it was observed that the impurities, cyclohexyl analogue and R,S, S-Diketopiparazine coeluted at the ph variation. To further verify the ph effect, the buffer ph variation was reduced by ± 0.1 units and analysis was repeated. At this ph variation there was good separation of all the impurities, indicating the ph variation of mobile phase 2.4 ± 0.1 is suitable for analysis Conclusion The simultaneous method developed can be used for estimation of impurities of Lisinopril and Hydrochlorothiazide in fixed dose combination tablets formulation. This method can be effectively used for stability studies of the drug product. The developed method was validated as per ICH method validation protocol and all parameters were acceptable
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