CHAPTER-5. Sumatriptan Succinate
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1 110 CHAPTER-5 Sumatriptan Succinate
2 111 CHAPTER-5 Chapter-5 : Sumatriptan succinate S. No. Name of the Sub- Title Page No. 5.1 Introduction Experimental Method validation Procedure Result& Discussion Conclusion 134
3 112 CHAPTER Introduction Sumatriptan Succinate is a triptan sulfa drug including a sulfonamide cluster. It is utilized for the cure of migraine headaches. Chemically named as 1-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]-Nmethyl methane sulfonamide. The chemical structure of sumatriptan succinate is shown in fig.5.1 Structurally, it is an analog of the obviously taking place neuro-active alkaloids dimethyltryptamine (DMT), 5-methoxy-dimethyl tryptamine and bufotenine, with an N- methyl sulfonamidomethyl- cluster at situation C-5 on the indole ring. 93 Fig. 5.1: Structure of Sumatriptan succinate The different analytical techniques have been statement in place of the EP 94 and U.S Pharmacopeia 95, sumatriptan succinate containing four impurities. Several efforts were made to expand a stability representative LC , methodology for assessment of related impurities of Sumatriptan succinate in the tablets formulations of sumatriptan succinate and naproxen. In the current experimentation, we illustrate a RP-HPLC technique for the severance and quantification of progression impurities of Sumatriptan succinate. The specificity, accuracy,
4 Imp-C Imp-D 113 quantification limit (LOQ), detection limit (LOD), precision and robustness of the technique was resolute as per the ICH strategy and establish to be appropriate for quality declaration of Sumatriptan succinate. The processed impurities were mentioned in below table.5.1. Table 5.1: Sumatriptan succinate impurities Impurity Chemical structure Chemical Name Molecular Weight Imp-A 1-(3-(2-dimethyl amino) ethyl)-2((3-(2-(dimethyl amino)ethyl)-1h-indole-5- yl)-n-methylmethane foramide Imp-B N-Methyl-1-(3-2-(methyl amino)ethyl)-1h-indole yl) methanesulfoamide 1-(3-(2-(dimethyl amino)ethyl)-1-(hydroxy methyl)-1h-indole-5-yl)- N-methylmethane sulfonamide 1-(3-(2-(dimethyl amino)ethyl)-1h-indole-5- yl)-n-methylmethane sulfonamide N-oxide
5 Imp-E (3-(2-aminoethyl)-1Hindole-5-yl)-N-methyl methane sulfonamide Experimental Chemicals Reference material of standard of Sumatriptan succinate and impurities specifically impurity-a, B, C, D and E be received gift samples from M/s Dr Reddys Laboratories Ltd, Hyderabad, India. All other chemicals employed were of analytical rating if acknowledged or else. Acetonitrile, Milli Q water and KH2PO4, Orthophosphoric acid were procured from Merck (Germany) Instruments The High performance liquid chromatography system was arranged through pumps having quaternary channels with auto injector and auto sampler (Replica: Alliance 2695, create :Waters) associated with PDA detector restricted with Empower software ( Make: Waters ) Preparation Standard and sample solutions The analyte and standard deliberation for assay were 0.125, 0.250, 0.375, 0.50, 0.625, and 0.75 mg/ml were arranged to conduct the linearity studies. Stock solutions of Sumatriptan succinate (0.5mg/mL) as well as all impurities (0.5mg/mL) were arranged in eluent for purity by HPLC. The impaled solution were primed by taking 50% 100% and 150% of all impurities in eluent stock solutions for the assessment of quantification limit, limit of detection, Accuracy, linearity and
6 115 precision in concord with ICH strategy. Sumatriptan succinate analyte solution from stock solution is spiked with the concentration of 0.05% to 0.30% of all impurities to find precision, robustness and ruggedness. The amount of impurities were deliberate from peak areas Chromatographic conditions The eluent-a consists of 0.05 M KH2PO4 buffer ph attuned 4.5 with dilute H3PO4 and eluent-b consists of 10% aqueous in Acetonitrile, filtered during 0.45 µm filter and degassed by make use of ultrasonicator for 5 minutes earlier to utilize. The instrument was equilibrated for some time until clear base line and analysis was performed in gradient circumstances make use of a flow rate of the eluent was held at 1.0 ml/min at 35 o C temperature. chromatograms were examined at 225 nm Wave length selection From the UV absorption spectra of every recognized impurities, the detection for supervising the impurities were preferred as 225 nm. absorption spectrum of Sumatriptan succinate and its impurities certification in HPLC system make use of PDA recognition. The UV absorption spectrum of Sumatriptan succinate and associate impurities are about 225 nm. Consequently, wavelength 225 nm is preferred for the division and quantification of processed impurities in Sumatriptan succinate (Fig.5.2)
7 116 Fig. 5.2: UV spectrums of Sumatriptan succinate impurities Stationary phase and Eluent selection The purpose of this study is to divide Sumatriptan succinate from impurity-a, B, C, D and E. The impurities were not alienated with Sumatriptan succinate and also co-eluted applying dissimilar stationary phases like Phenyl,C18 and C8 as well as dissimilar eluents.
8 117 Experiment - 1 Column Eluent-A : Zorbax C8, 150mm X 4.6, with 3.5 microns : 0.05 M potassium dihydrogen orthophosphate in 1000ml Milli-Q-Water, ph attuned to 4.5 through dil. ortho phosphoric acid Eluent-B Flow rate Detection Diluent Elution : 10% aqueous in Acetonitrile : 1.0 ml/min : 225 nm : Eluent-A and B(1:1 ratio) : Gradient Gradient Program(T/%B) : 0/20, 4/20, 10/50, 18/50, 18.5/20 and 20/15 Column Temp. Run time : 35 o C : 15 min Injection volume : 1 μl Fig. 5.3: Representative chromatogram of blend solution Observation: In this experiment we observed impurity-b and Sumatriptan succinate peak are eluting same retention time. So need to change column polarity, hence we go for C18 column for further experiment.
9 118 Experiment - 2 Experimental conditions were same as above experiment-1, only stationary phase change from C8 to C18. Observation: Even though by changing C18 stationary phase,there is no separation between impurity-b and Sumatriptan succinate peak. Hence we need to further development with different stationary phase like phenyl and cyano column. Experiment - 3 Column Eluent-A : Zorbax phenyl 150 mm X 4.6mm and 3.5 microns : 0.05 M potassium dihydrogen orthophosphate ph attuned to 4.5 with dil.h3po4 Eluent-B Flow rate Wavelength Diluent Elution : Acetonitrile : 1.0 ml/min : 225 nm : the proportion of 1:1 Eluent-A and B : Gradient Gradient Program(T/%B) : 0/15, 4/15, 10/50, 18/30, 13.5/15 and 20/15 Column Temp. Injection volume : 35 o C : 1 μl Fig. 5.4:Representative chromatogram of blend solution
10 AU IMP-E IMP-C IMP-B SUM IMP-A IMP-D Conclusion In this experiment selectivity of sumatriptan and impurity -C is varying and impurity-b, impurity-c and Sumatriptan succinate peaks were separated with low resolution. So phenyl column was also not suitable for the separation of impurity-b, impurity-c and Sumatriptan succinate. Experiment - 4 Column Eluent-A : Zorbax CN, 150 mm X 4.6 mm, 3.5 microns : 0.05 M potassium dihydrogen orthophosphate ph attuned to 4.5 with dil.h3po4. Eluent-B Flow rate Wavelength : 100% Acetonitrile : 1.0 ml/min : 225 nm Diluent : Eluent-A and B in the proportion of 1:1 Elution mode : Gradient Gradient Program(T/%B) : 0/15, 5/15, 10/70, 12/70, 13.1/15 and 20/15 Column Temp. : 35 o C Injection volume : 1 μl Minutes Fig. 5.5:Representative chromatogram of blend solution
11 AU IMP-E IMP-B IMP-C SUMATRIPTAN IMP-D IMP-A Conclusion In this experimentation the resolution among Impurity B & Impurity C was below 1.5, and all other peaks good separation observed,so need to optimize solvent strength in eluent -B. Experiment - 5 Column Eluent-A : Zorbax CN, 150mm X 4.6mm, 3.5 microns : 0.05 M potassium dihydrogen orthophosphate ph attuned to 4.5 with dil. H3PO4 Eluent-B Flow rate Detection : 10% aqueous in Acetonitrile : 1.0 ml/min : 225 nm Diluent : Eluent-A and B in the proportion of 1:1 Mode of Elution : Gradient Gradient Program(T/%B) : 0/15, 5/15, 10/55, 12/55, 13.1/15 and 15/15 Column Temp. Run time : 35 o C : 15 min Injection volume : 1 μl Minutes Fig. 5.6:Representative chromatogram of blend solution
12 121 Conclusion From the above experimental conditions we observed good separation between impurity-b, impurity-c and Sumatriptan succinate. The resolution among all impurities from Sumatriptan succinate is exceeding 1.5 and symmetrical peak nature was observed. From the data, the appropriate chromatographic division was accomplished on an Zorbax Cyano 150 mm 4.6 mm, 3.5 μm column. The Eluent-A consists of buffer 0.05 M KH2PO4, ph attuned to 4.5 with dil. ortho phosphoric and Eluent-B consists of water - acetonitrile 10:90 (v/v). The eluent flow rate was reserved at 1.0 ml/ min, temperature of column maintained at 35 C, the peak nature of the Sumatriptan succinate was symmetrical. In finalized chromatographic circumstances Sumatriptan succinate, impurity-a, B, C, D and E were alienated with resolution exceeding 1.5, retention time of impurities about 6.02 min, 9.15 min,5.19min, 5.53 min,8.92 min and 4.42 min, respectively. 5.3 Method validation Procedure Specificity The specificity of HPLC technique for Sumatriptan succinate was performed in the occurrence of impurities i.e. impurity-a, B, C, D and E. Stability representative possessions and specificity of the anticipated technique were conducted with the aid of forced degradation studies for sumatriptan succinate bulk drug premeditated humiliation was effort to stress situation of UV light at
13 nm, thermal humiliation at 105 C, hydrolysis of 0.1 N HCl acid at 70 C, base hydrolysis of 0.1N NaOH at 70 C and oxidation hydrolysis at 3.0 % H2O2 to estimate the aptitude of the anticipated LC method to division of Sumatriptan succinate from its humiliation products. The experimentation time was 10 days for thermal and UV light degradation experimentation, for the hydrolysis of a base and acid for 12 Hrs, oxidation for was 24 Hrs. Peak purity experiment was performed for the Sumatriptan peak by employed PDA detector in strain samples. The Assay test was performed for stress samples in opposition to eligible Sumatriptan succinate reference standard. Assay was also deliberate for Sumatriptan succinate analyte by spiking all impurities at 0.15 % Precision The precision for assay technique was estimated for Sumatriptan succinate test sample in opposition to a qualified primary standard. Six independent assays were conducted and calculated the % RSD for replicate assay determinations. Six individual arrangements of Sumatriptan succinate(0.5 mg/ml) spiked with 0.15% level of all impurities pertaining to Sumatriptan succinate analyte concentration were considered for the evaluation of precision of the related substance technique and % Relative standard deviation of area for every impurity was deliberate for six replicate injections.
14 Quantification limit (QL) and Detection Limit (DL) The quantification limit (LOQ) and detection limit (LOD)can be resolute by quantifying the importance of analytical environment. The LOQ and LOD were indomitable from slope signal-to- noise relation method. The LOQ and LOD pro impurity-a, B, C, D and E were indomitable by injecting a sequence of dilutions with recognized concentration solutions Linearity Test solutions to evaluate linearity for the assay technique were arranged from Sumatriptan succinate stock solutions at different concentrations from 25% to 150 % of assay concentration i.e, 0.125, 0.250, 0.375, 0.5, and 0.75 mg/ml respectively. The concentration versus peak area information was generated by leastsquares linear regression study. Test solutions to evaluate linearity for the purity technique be arranged by reducing stock solutions to get the necessary concentration levels. The solutions were ready at different concentration amount from 50% to 200 % (0.5 mg/ml) of the measurement level i.e 0.15% Accuracy The assay technique was estimated in triplicate at three dissimilar concentration amount, i.e. 50%, 100% and150% level regarding test concentration. The percentage of recoveries was deliberate. The accuracy study of purity of sumatriptan succinate was performed in triplicate concentrations amount at 50%,100% and
15 %of the Sumatriptan succinate requirement level i.e 0.15%. Calculated the percentages of revitalization for impurities Robustness The robustness of the industrial LC technique was estimated by intentionally changing experimental situations and the resolution among Impurity-B and Impurity-C, Impurity-C and sumatriptan was documented. The conditions which were altered deliberately were flow rate of the eluent, temperature of the column oven and ph variation for conducting flow of the eluent was 1.0 ml/min. The outcome of flow rate on the declaration was examined with a flow 0.8 and 1.2 ml/min respectively, as an alternative of 1.0 ml/min. The achievement of the different temperature on declaration was deliberate at 35 C and 45 C as an alternative of 40 C Mobile phase stability and Solution stability The solution strength of Sumatriptan succinate in the assay technique was executed by parting together the solutions of reference standard and sample in strongly restriction flasks at ambient temperature for 48 Hrs. The similar sample solutions were performed assayed for every 6 Hrs intermission up to the final time era. The eluent stability was also executed by assaying the newly arranged sample solutions in opposition to newly arranged reference standard solution for every 6 Hrs intermission up to 48 Hrs. Eluent arranged was kept reliable throughout the experimentation period. The % RSD
16 125 for the assay of Sumatriptan succinate was considered throughout the solution and mobile stability trials. The solution stability of Sumatriptan succinate and its impurities in the purity technique was conducted by parting spiked sample solutions in strongly capped flasks at ambient temperature for 48 Hrs. Substance of each impurity was indomitable for every 12 Hrs intermission up to the experiment period. The eluent stability was in addition conducted for 48 Hrs by introducing the newly arranged sample solutions for each 12 Hrs intermission. Substance of related impurities were ensured in the test solutions. 5.4 Results and discussion Specificity During forced degradation studies, it was experiential that the humiliation was not experiential in Sumatriptan succinate sample as subjected to stress circumstances like thermal, photolytic and base hydrolysis. Sumatriptan succinate was tainted to imp-a in acid hydrolysis and was despoiled to imp- A and E beneath oxidation. Peak purity outcome accomplished by employing Photo diode array detector established that the Sumatriptan succinate peak is pure and homogenous in all the investigated stress analytes. The assay of Sumatriptan is unchanged in the occurrence of all known impurities and its humiliation products authenticates the stability representative strength of the methodology. The review of forced humiliation results is mentioned in below table-5.2
17 AU Peak IMP-B IMP-C SUMATRIPTAN IMP-A Peak Table 5.2: Specificity Results Degradation condition Time % degradation Peak Purity As such sample NA NA Pass Acid hydrolysis 24hr 1.56 Pass Base hydrolysis 24hrs 2.88 Pass Oxidation 24hrs 0.04 Pass Thermal (105 C) solid 10days 0.02 Pass Photo degradation at 254nm 10days 0.05 Pass Water hydrolysis at 70 C 24 hrs 0.03 Pass Minutes Fig. 5.7: Representative chromatograms of Sumatriptan succinate Fig. 5.8: Representative chromatogram of base hydrolysis
18 127 Fig. 5.9: Representative chromatogram of Oxidation degradation Fig. 5.10: Representative chromatogram of Acid degradation Method validation results System suitability The system suitability solution was introduced for the Assay and estimated the% RSD for reproduce injections were ealuated in below table 5.3. The system suitability solution was introduced for purity method and chromatographic constraint like plate count, resolution and tailing factor and were estimate in table 5.4.
19 128 Table 5.3: Assay System suitability results S.No Area Sumatriptan succinate Peak Avgerage STDEV % RSD 1.18 Table 5.4: System suitability results for Purity Parameter Imp-E Imp-B Imp-C SUM Imp-D Imp-A Rt RRT Rs N Asymmetry factor Precision The % RSD of Sumatriptan throughout the assay method precision experimentation was below 1.2% and % RSD for the area impurity-a, B, C, D and E in purity methodology was less than 5.0%. The % RSD of the assay outcome achieved in the intermediate precision experimentation was below 1.2 % and the % RSD area of impurity-a, impurity-b, impurity-c, impurity-d for the and impurity-e were below 4.5 %, complaint superior precision of the technique.
20 129 Table 5.5: Precision (% RSD, n=6) Compound Rt RRT % RSD Impurity-A Impurity-B Sumatriptan ( Assay) Impurity-C Impurity-D Impurity-E Limit of detection and quantification The detection limit for all the impurities specifically impurity-a, B, C, D and E was capable at % for 1 μl injection volume. The limit of quantification for all above five impurities namely Impurity-A, Impurity-B, Impurity-C, Impurity-D and Impurity-E was capable at % for injection volume of 1 μl. The correctness at LOQ level concentration for A, B, C, D and E impurities were lower than 3.6%. The accuracy at LOQ level of all impurities between % Table 5.6: LOD and LOQ data for Impurities Compound Rt RRT LOD ( %) LOQ(%) Impurity-A Impurity-B Sumatriptan Impurity-C Impurity-D Impurity-E
21 Linearity The calibration curve for linearity of the assay methodology was achieved over the calibration series experienced i.e mg/ml and correlation coefficient acquired was in excess of Linearity was performed for the assay methodology above the similar concentration series for 3 different days. The % RSD principles of the Y-intercept of the calibration arc and slope were 0.56 and 1.43, correspondingly. The consequence proves that an outstanding correlation survived among the concentration of the analyte and peak area. Conc. in mg/ml Table 5.7: Sumatriptan Linearity Area Correl.Coefficient Slope Y-Intercept y = 1E+07x R² = The calibration plot for Linearity study of the purity method for related impurities was gained above the calibration series tested, i.e % to 0.3% for all impurities namely, impurity-a, impurity-b, impurity-c, impurity-d and impurity-e. The correlation coefficient achieved was exceeding The above result proves that an admirable correlation survived among the concentration of imp-a, B, A R E A LINEARITY OF SUMATRIPTAN CONCENTRATION, MG/ML
22 131 C, D and E and peak areas of impurities. Linearity data of all impurities data mentioned in below table 5.8. Table 5.8: Impurities Linearity data S.No % Imp -A Imp -B Imp -C Imp -D Imp -E Conc Correlation coefficient Y-Intercept Slope A R E A LINEARITY OF IMPURITY-A y = 3E+06x R² = CONCENTRATION, MG/ML A R E A LINEARITY OF IMPURITY-B y = 9E+06x R² = CONCENTRATION, MG/ML
23 132 A R E A LINEARITY OF IMPURITY-C y = 1E+07x R² = CONCENTRATION, MG/ML A R E A LINEARITY OF IMPURITY-D y = 4E+06x - 52 R² = CONCENTRATION, MG/ML A R E A LINEARITY OF IMPURITY-E y = 9E+06x R² = CONCENTRATION, MG/ML Fig. 5.9:Linearity graphs for (a) Impurity-A (b) Impurity-B (c) Accuracy Impurity-C (d) Impurity-D (e) Impurity-E The recovery for assay of Sumatriptan analyte was series from to %. The % recovery of all five impurities in Sumatriptan samples different beginning 88.5 to %. The details of the study were listed in the table 5.9.
24 133 Table 5.9:Results for Accuracy (% Recovery, n=3 ) Compound Rt RRT Recovery Impurity-A % Impurity-B % Sumatriptan % Impurity-C % Impurity-D % Impurity-E % Robustness The Robustness of the methods was fruitfully demonstrated and in all the deliberately various chromatographic circumstances such as column temperature, flow rate and variation of ph, the resolution among critical pair, i.e. Imp-B and C, impurity-c and Sumatriptan were exceeding 1.5, representing the robustness of the method. The outcomes achieved from all the deliberately varied condition were summarized in the table 5.10 Table 5.10: Results for Robustness Parameter Imp-A Imp-B Imp-C SUM Imp-D Imp-E Rt RRT Different Flow, ml/min Different buffer ph Different Column Temperature, o C
25 stability of Solution and Eluent stability The % RSD (n=6) of the assay of Sumatriptan for the duration of solution constancy experimentation were contained by 0.8 %. No considerable alterations were experiential in the content of related substances of Sumatriptan specifically impurity-a, B, C, D and E throughout eluent stability and solution stability testing when executed employing the purity method. The mobile phase constancy and solution stability testing data authenticate that the mobile phases and sample solutions utilized throughout assay and the purity functions were stable for not less than 48 hrs. 5.5 Conclusion The RPLC technique made-up for quantitative and qualitative willpower of Sumatriptan and its related impurities were specific, accurate, rapid, and precise. The technique was wholly authenticated viewing adequate information for all the technique confirmation constraints experienced. The developed technique is stability representative and can be easily utilized by analytical laboratories/pharmaceutical industries to establish the purity and assay in normal sumatriptan succinate production as well as stability samples.
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