Nota Técnica. Quim. Nova, Vol. 35, No. 4, , 2012
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1 Quim. ov, Vol. 35, o. 4, , 2012 DEVELPMET AD VALIDATI F A VEL STABILITY IDICATIG RP-UPLC METHD FR SIMULTAEUS DETERMIATI F IZATIDIE, METHYLPARABE AD PRPYLPARABE I RAL LIQUID PHARMACEUTICAL FRMULATI vneet Kumr*, Bhupendrsinh Vghel nd P. Sunil Reddy Dr. Reddy s Lbortories Ltd., IPD, Bchuplly, Hyderbd , A.P, Indi D. Sngeeth Deprtment of Chemistry, S.A.S., V.I.T. University, Vellore , Tmilndu, Indi Recebido em 24/8/11; ceito em 12/10/11; publicdo n web em 4/1/12 ot Técnic A selective nd ccurte stbility-indicting grdient reverse phse ultr performnce liquid chromtogrphic method hs been developed nd vlidted for the simultneous determintion of niztidine, methylprben nd propylprben in phrmceuticl orl liquid formultion. The seprtion ws chieved on Acquity UPLC TM HSS T3 1.8 µm column by using mobile phse contining grdient mixture of solvent A (0.02 Mol L -1 KH 2 P 4, ph 7.5) nd B (60:40 v/v mixture of methnol nd cetonitrile) t flow rte of 0.4 ml min -1. Drug product ws exposed to the stress conditions of oxidtive, cid, bse, hydrolytic, therml nd photolytic degrdtion. The developed method ws vlidted s per interntionl ICH guidelines with respect to specificity, linerity, ccurcy, precision nd robustness. Keywords: niztidine; stbility-indicting; UPLC-UV. ITRDUCTI iztidine is histmine H2-receptor ntgonist commonly used in the tretment of gstroesophgel reflux disese, duodenl nd gstric ulcertion. Its chemicl designtion is -[2-[[[2-[(dimethylmino) methyl]-4-thizoyl] thio]- -methyl-2-nitro-1,1-ethenedimine (Figure 1). 1 iztidine cn be found in mny phrmceuticl forms such s tblets, cpsules, injections nd orl liquids. Compred to tblet nd cpsule, liquid formultions fvour most rpid bsorption of ctive substnce. Liquid preprtions re prticulrly suceptible to mocrobil growth becuse of the nture of their ingrdtient. Such preprtions require the presence of preservtives nd ntimicrobil gents, to prevent chemicl ltertion nd degrdtion of drug substnce. () (b) H S Figure 1. Structures of () niztidine, (b) methylprben nd (c) propylprben Prben, group of lkyl esters of p-hydroxybenzoic cid re widely used s ntimicrobil preservtives in cosmetics, food nd phrmceuticl products. 2 The prbens re effective over wide ph rnge nd present brod sprectrum of ntimicobil ctivity, lthough they re most effective ginst yest nd molds. Methylprben nd *e-mil: nvneetrjpoot21@yhoo.com S (c) H H H + propylprben hve been used for the preservtion of niztidine orl solution (Figure 1b-c). The nlysis of these preservtives in commercil phrmceuticl product is prticulrly importnt for both, qulity ssurnce nd consumer protection. Indin drugs nd cosmetics ct 3 nd Interntionl Conference on Hrmoniztion (ICH) 4 guidnce recommends tht relese nd stbility testing for preservtive content should be performed nd finished product self-life specifiction should lso include identifiction test, preservtive content nd limits for ntimicrobil preservtive present. Therefore, the nlysis of niztidine into orl solution in combintion with preservtive is required nd essentil. Some liquid chromtogrphy (LC) methods re vilble for the determintion of niztidine in biologicl fluids. 5-8 Literture reported the HPLC nlysis for fmotidine, rnitidine, cimetidine nd niztidine in drug products nd stbility indicting LC method for niztidine nd its impurities. 9,10 iztidine monogrph is lso listed in United Sttes Phrmcopoie (USP) 11 nd Europen Phrmcopoei (Eur. Ph.). 12 USP monogrph describes chromtogrphic ssy method for niztidine with runtime of 40 min nd Ph.Eur. describes ssy method for niztidine with runtime of 25 min. o phrmcopoeil monogrph is vilble for niztidine orl solution. Severl nlyticl procedures hve been reported for the determintion of methylprben nd propylprben sepertely or in combintion with the other drugs by LC nd other techniques These methods my not be suitble for simultneous determintion of niztidine, methylprben nd propylprben together in one chromtogrphic run. To the best of our knowledge, there is no stbility indicting LC method reported for the estimtion of niztidine, methylprben nd propylprben in orl liquid formultion. Therefore, ttempts were mde in this study to develop fst, sensitive, selective, robust nd stbility indicting reverse phse ultr-performnce liquid chromtogrphy (UPLC) method for the simultneous determintion of niztidine, methylprben nd propylprben in orl liquid formultion. The developed LC method ws vlidted with respect to specificity, linerity, precision, ccurcy nd robustness. Force degrdtion studies were performed on the plcebo nd drug products. Developed method seprtes ll degrdtion products from niztidine, methylprben nd
2 828 Kumr et l. Quim. ov propylprben, nd exhibits stbility indicting nture. These studies were performed in ccordnce with estblished ICH guidelines. 18,19 Developed method cn be used for routine nlysis of production smples nd stbility testing of the niztidine orl solution to ensure the qulity of the product. EXPERIMETAL Regents nd chemicls iztidine stndrd (99.6% pure) nd orl solution ws supplied by Dr. Reddy s lbortories limited, Hyderbd, Indi. Methylprben (99.9% pure) nd propylprben (100% pure) were procured from United Stte Phrmcopoei (USP). The high performnce liquid chromtogrphy (HPLC) grde cetonitrile nd methnol; nd nlyticl grde potssium di-hydrogen ortho-phosphte nd sodium hydroxide were purchsed from Merck, Mumbi, Indi. High purity wter ws prepred by using Millipore Milli-Q Plus wter purifiction system (Millipore, Milford, MA, USA). Instrumenttion nd chromtogrphic conditions The chromtogrphy nlysis ws performed using Wters Acquity TM UPLC seprtion module (Wters Corportion, Milford, USA) equipped with photo diode rry (PDA) detector, binry solvent mnger nd uto smpler system. The output signl ws monitored nd processed using Empower 2 softwre. The seprtion ws chieved on Acquity UPLC TM HSS T3 (100 x 2.1 mm) 1.8 µm column (Wters Corportion, Milford, USA) with mobile phse contining grdient mixture of solvent A (0.02 Mol L -1 potssium dihydrogen ortho-phosphte, ph djusted to 7.5 with sodium hydroxide solution) nd B (60:40 v/v mixture of methnol nd cetonitrile) t flow rte of 0.4 ml min -1. The grdient progrm (Time (min)/%b) ws set 0/20, 1/25, 5/37, 7/55, 8/65, 8.5/65, 8.6/20 nd 10/20. The column oven temperture ws mintined t 35 C nd eluted compounds were monitored t the wvelength of 254 nm. The smple injection volume ws 4 µl. Cintex digitl wter bth ws used for hydrolysis studies. Photo-stbility studies were crried out in photo-stbility chmber (Snyo, Leicestershire, UK). Therml stbility studies were performed in dry ir oven (Cintex, Mumbi, Indi). The ph of the solutions ws mesured by ph meter (Mettler-Toledo, Switzerlnd). Preprtion of stndrd solution Solvent A nd methnol in the rtio of 80:20 v/v ws used s diluent. A stock solution of niztidine (0.6 mg ml -1 ) ws prepred by dissolving n pproprite drug in diluent. The stock solutions of methylprben (0.72 mg ml -1 ) nd propylprben (0.2 mg ml -1 ) were prepred in methnol, seprtely. A mixed stock solution contining 72 µg ml -1 methylprben nd 8 µg ml -1 of propylprben ws prepred from their respective stock solutions. Working stndrd solution ws prepred in diluent from mixing bove stock solutions of niztidine, methylprben nd propylprben with finl concentrtion of 120, 14.4 nd 1.6 µg ml -1, respectively. Clibrtion curves were prepred by diluting stock solutions of niztidine, methylprben nd propylprben with diluent to get series of solutions contining finl concentrtions of 0.34, 11.9, 59.6, 89.5, 119.3, nd µg ml -1 for niztidine; nd 0.11, 1.45, 7.26, 10.9, 14.5, 16.7 nd 21.8 µg ml -1 for methylprben; nd 0.07, 0.16, 0.82, 1.22, 1.63, 1.88 nd 2.45 µg ml -1 for propylprben. A grph ws plotted s concentrtion of nlyte versus pek re response nd found to be liner for ll three nlytes. Preprtion of smple solution An mount (bout 2 g) of orl solution equivlent to 30 mg niztidine ws trnsferred into 50 ml volumetric flsk, dded 35 ml of diluent nd ultrsonicted for 10 min, nd then diluted to volume with diluent. 5 ml of this solution ws diluted to 25 ml with diluent, to give solution contining 120 µg ml -1 of niztidine, 14.4 µg ml -1 of methylprben nd 1.6 µg ml -1 of propylprben (Figure 2). RESULTS AD DISCUSSI Method development nd optimiztion The min objective of the chromtogrphic method ws to seprte nd quntitte nizitidine, methylprben nd propylprben in presence other plcebo components like flvor gents nd colors. An isocrtic method employed using 0.02 Mol L -1 potssium dihydrogen ortho-phosphte (ph 3.0) nd cetonitrile in the rtio of 70:30 s mobile phse, Acquity UPLC BEH Shield (150 x 2.1 mm) 1.7 µm column with flow rte of 0.4 ml min -1 on UPLC equipped with photo diode rry detector. iztidine pek ws eluted too erly long with plcebo peks nd propylprben retined strongly. To retin nd seprte niztidine from plcebo peks nd reduce the run time n ttempt ws mde with grdient elution with mobile phse 0.02 Mol L -1 potssium dihydrogen ortho-phosphte buffer (ph 3.5) s solvent-a nd solvent-b (mixture of cetonitrile nd wter in the rtio of 80:20 v/v). iztidine ws retined but mny plcebo peks co-eluted with niztidine. To resolve the niztidine from plcebo, solvent A modified to 0.15 Mol L -1 mmonium formte hving ph 5.5 nd Acquity UPLC TM HSS T3 (100 x 2.1 mm) 1.8 µm selected for seprtion. But stisfctory resolution ws not chieved between niztidine nd plcebo peks. To chieve good seprtion, solvent A modified to 0.02 Mol L -1 potssium dihydrogen ortho-phosphte buffer (ph 7.5) nd solvent B modified to mixture of methnol nd cetonitrile in the rtio of 60:40 (v/v), respectively. n the optimiztion of grdient progrm, niztidine, methylprben nd propylprben peks wre well resolved form ech other nd plcebo peks with shorter run time. Bsed on these experiments, the finl optimized conditions re described below. Acquity UPLC TM HSS T3 (100 x 2.1 mm) 1.8 µm ws used s the sttionry phse. The mobile phse A consist of 0.02 Mol L -1 potssium dihydrogen ortho-phosphte hving ph 7.5 nd mobile phse B contined mixture of methnol nd cetonitrile in the rtio of 60:40 (v/v). The flow rte ws 0.4 ml min -1 with grdient progrm of (time (min)/ %B) 0/20, 1/25, 5/37, 7/55, 8/65, 8.5/65, 8.6/20 nd 10/20. The column temperture ws mintined t 35 C nd detection ws monitored t 254 nm. The injection volume ws 4 µl. The typicl reltive retention time of methylprben nd propylprben with respect to niztidine were 1.38 nd 2.58, respectively. Vlidtion of the method The proposed method ws vlidted by determining its performnce chrcteristics regrding specificity, ccurcy, precision, limit of detection nd quntifiction, linerity, rnge nd robustness. 18,19 System suitbility System suitbility shll be checked for the conformnce of suitbility nd reproducibility of chromtogrphic system for nlysis. System suitbility ws determined before smple nlysis from five replicte injections of the stndrd solution contining 120, 14.4 nd 1.6 µg ml -1 of niztidine, methylprben nd propylprben, respectively. The cceptnce criteri were less thn 2% reltive stndrd
3 Vol. 35, o. 4 Development nd vlidtion of novel stbility indicting RP-UPLC method 829 Tble 1. System suitbility results of precision nd intermedite precision study Compound USP Tiling %RSD Intermedite USP Tiling % RSD iztidine Methylprben Propylprben % RSD of the nlyte pek res from five replicte injections. Specificity/stress studies Specificity is the bility of the method to mesure the nlyte response in the presence of its potentil degrdnts nd plcebo mtrix. In the present study, injections of blnk nd plcebo were performed to demonstrte the interference with the elution of niztidine, methylprben nd propylprben. These results demonstrte tht there ws no interference from the other compounds nd, therefore, confirms the specificity of the method (Figure 2b). Force degrdtion studies of drug product were lso performed to evlute the stbility-indicting property nd specificity of proposed method. The solutions of drug product nd plcebo were exposed to cid hydrolysis (1 Mol L -1 HCl t 60 C for 2 h), bse hydrolysis (1 Mol L -1 H t 60 C for 15 min), oxidtion (3% H 2 2 t room temperture for 5 min), hydrolytic (wter t 60 C for 24 h), therml (105 C for 2 h) nd photolytic degrdtion (drug product exposed to visible light for 240 h resulting n overll illustrtion 1.2 million lux hours nd UV light for 250 h resulting n overll illustrtion 200 w h/m 2 t 25 C). Significnt degrdtion observed during cid, bse hydrolysis nd oxidtive degrdtion (Figure 2c-e). Pek purity test ws crried out for the niztidine, methylprben nd propylprben peks by using PDA detector in stress smples. The purity of ll three substnces ws unffected by the presence of degrdtion products, nd, thus confirms the stbility-indicting power of the developed method. A summry dt of stress study is shown in Tble 2. Limits of detection (LD) nd quntifiction (LQ) The LD nd LQ were determined t signl-to-noise rtio of 3:1 nd 10:1, respectively, by injecting series of dilute solutions with known concentrtions. The limit of detection nd limit of quntifiction vlues re reported in Tble 3. Linerity Figure 2. Typicl chromtogrms of () smple preprtion, (b) overly chromtogrms of blnk, plcebo nd smple (c) cid degrdtion smple treted with 1 Mol L -1 HCl t 60 C for 2 h, (d) bse degrdtion smple treted 1 Mol L -1 H t 60 C for 15 min nd (e) oxidtive degrdtion smple treted with 3% H 2 2 t room temp for 5 min. Chromtogrphic conditions: Acquity UPLC TM HSS T3 (100 x 2.1 mm) 1.8 µm column t 35 C; mobile phse A: 0.02 Mol L -1 KH 2 P 4, ph 7.5 nd mobile phse B: methnol nd cetonitrile (60:40; v/v); 0.4 ml min -1 of flow rte; grdient progrm: (time (min)/ %B) 0/20, 1/25, 5/37, 7/55, 8/65, 8.5/65, 8.6/20 nd 10/20; wvelength of 254 nm devition (RSD) for pek res, USP tiling fctor less thn 2.0 for niztidine, methylprben nd propylprben peks from stndrd solution. All criticl prmeters tested met the cceptnce criteri (Tble 1). Linerity test solutions were prepred by diluting the stock solutions to the required concentrtions. The solutions were prepred t seven concentrtion levels from LQ to 150% levels of test concentrtion (LQ- 180 µg ml -1 for niztidine, LQ µg ml -1 for methylprben nd LQ- 2.4 µg ml -1 for propylprben). Clibrtion curves were plotted between the responses of pek versus nlyte concentrtions. The coefficient correltion, slope, y-intercept of the clibrtion curve nd % bis t 100% response re reported (Tble 3) nd result shows tht n excellent correltion existed between pek re nd concentrtion of niztidine, methylprben nd propylprben. The precision of method ws verified by repetbility nd
4 830 Kumr et l. Quim. ov Tble 2. Summry of forced degrdtion results Stress Condition Acid hydrolysis (1 Mol L -1 HCl t 60 C, 2 h) Bse hydrolysis (1 Mol L -1 H t 60 C, 15 min) xidtion (3% H 2 2 t room temp, 5 min) iztidine Methylprben Propylprben % Degrdtion Purity ngle Purity threshold Purity ngle Purity threshold Purity ngle Purity threshold Therml (At 105 C, 3 h) Hydrolytic (Wter t 60 C, 24 h) Photolytic (1.2 million lux h visible light nd 200 wh/m 2 UV light) Tble 3. Evlution of LD, LQ nd linerity dt Prmeter iztidine Methylprben Propylprben LD (µg/ml) LQ (µg/ml) Correltion coefficient Intercept () Slope (b) Bis t 100% response intermedite precision. Repetbility ws checked by injecting six individul preprtions of niztidine orl solution contining niztidine, methylprben nd propylprben t 10, 100 nd 125% level of test concentrtion (11.9, 119.3, µg ml -1 for niztidine, 1.45, 14.5, 18.1 µg ml -1 for methylprben, 0.16, 1.6, 2.0 µg ml -1 for propylprben). The intermedite precision of the method ws lso evluted using different nlyst nd different instrument nd performing the nlysis on different dys. The reltive stndrd devition of the res of ech pek ws clculted nd found to less thn 0.9% in repetbility nd less thn 0.7 % in intermedite precision, which confirms the good precision of the method. The %RSD vlues re presented in Tble 4. Tble 4. results determined during method vlidtion Prmeter Accurcy Amount spiked % RSD (n=6) iztidine Methylprben Propylprben Repetbility 10% Intermedite 100% % % % % Amount of ll three nlyte spiked with respect to trget concentrtion. Accurcy of the method for niztidine, methylprben nd propylprben ws evluted in triplicte t 10, 50, 100 nd 125% level of test concentrtion (11.9, 59.7, 119.3, µg ml -1 for niztidine, 1.45, 7.25, 14.5, 18.1 µg ml -1 for methylprben, 0.16, 0.8, 1.6, 2.0 µg ml -1 for propylprben). The percentge recoveries for ll three components were clculted (Tble 5). The percentge men recovery of niztidine, methylprben nd propylprben from the formultion vried from 98.8 to 101.2% indicting tht the developed method ws ccurte for the determintion of niztidine, methylprben nd propylprben in phrmceuticl formultion. Tble 5. Recovery results determined during method vlidtion Amount spiked Robustness The robustness of the method ws evluted during development by mking smll, but deliberte, chnges to the method prmeters. An experiment design ws used to determine how chnges in column temperture, flow rte nd mobile phse composition ffect the chromtogrphy of niztidine, methylprben nd propylprben. As shown in Tble 6, four fctors were evluted t two levels ech. A solution contining 120, 14.4 nd 1.6 µg ml -1 of niztidine, methylprben nd propylprben, respectively, ws ssyed ccording to the experimentl conditions listed in Tble-5. All of the experimentl conditions yielded cceptble results (Tble 7). Stbility of nlyticl solution % Recovery b iztidine Methylprben Propylprben 10% 99.1 ± ± ± % 98.9 ± ± ± % 99.7 ± ± ± % ± ± ± 0.3 Amount of ll three nlyte spiked with respect to trget concentrtion. b Men ± %RSD for three determintions Tble 6. Conditions for the robustness study Fctor Level Low (-) ominl High (+) ph MeH (%) Flow rte (ml min -1 ) Column temperture ( C) The solution stbility of niztidine, methylprben nd propylprben in the ssy method ws investigted by leving smple test solutions in tightly cpped volumetric flsk t room temperture for 24 h. The sme smple solutions were nlysed t the end of the study period ginst freshly prepred stndrd solutions. The vribility in
5 Vol. 35, o. 4 Development nd vlidtion of novel stbility indicting RP-UPLC method 831 Tble 7. Robustness results of UPLC method Expt. o. ABCD iztidine Methylprben Propylprben t R b A c T d K e t R A T K t R A T K 1 ominl A, ph; B, MeH (%); C, Flow rte (ml min -1 ); D, Column Temperture ( C). b Retention time (min) of the nlyte pek. c % RSD of the nlyte pek res from 5 injections. d Tiling fctor of the nlyte pek. e Cpcity fctor of the nlyte pek the ssy of ll three substnces ws within + 3% during solution stbility. The results from solution stbility experiments confirmed tht smple solution nd stndrd solutions were stble up to 24 h. CCLUSIS A simple nd efficient reverse-phse UPLC method ws developed nd vlidted for quntittive nlysis of niztidine, methylprben nd propylprben in phrmceuticl dosge forms. The method found to be precise, ccurte, liner, robust nd rugged during vlidtion. Stisfctory results were obtined from the vlidtion of the method. The method is stbility indicting nd cn be used for routine nlysis of production smples nd to check the stbility of the niztidine orl solution. ACKWLEDGEMET The uthors re thnkful to the mngement of Dr. Reddy s Lbortories Ltd., Hyderbd for providing fcilities to crry out this work. REFERECES 1. ccessed July Rieger, M. M.; Hndbook of phrmceuticl excipients, 2 nd ed., The phrmceuticl press: London, Deprtment of Helth, Government of Indi; Appendix IX, Stbility testing of new drugs, Drug nd cosmetics ct nd rules, 1940, p ICH Q6A; Specifictions: Test procedures nd cceptnce criteri for new drug substnces nd new drug products: Chemicl substnces, Interntionl Conference on Hrmoniztion, Yusuf, A.; Al Dgither, S.; Hmmmi, M. M.; Ther. Drug Monti. 2006, 28, Trcqui, A.; Kintz, P.; Mngin, P.; J. Chromtogr. Biomed. Appl. 1990, 529, Imre, S.; Vlse, L.; Leucut. S. E.; Rev. Roum. Chim. 2007, 52, Ashiru, D. A. I.; Ptel, R.; Bsit, A. W.; J. Chromtogr., B: Anl Technol. Biomed. Life Sci. 2007, 860, Ho, C.; Hung, H. M.; Hus, S. Y.; Shw, C. Y.; Chng, B. L.; Drug Dev. Ind. Phrm. 1999, 25, Gomes, A. R.; Rghurm, P.; Srirmulu, J.; Srinivs,.; Am. J. Anl. Chem. 2011, 2, The United Sttes Phrmcopoei, 34 th ed., The United Sttes Phrmcopoeil Convention: Rockville, Europen Phrmcopoei 4.2, Council of Europe, Hjkov, R.; Solich, P.; Dvoik, J.; J. Phrm. Biomed. Anl. 2003, 32, Seong, K.; Hsuck, K.; J. Phrm. Biomed. Anl. 1997, 15, Dine, K.; Bel, K.; J. Chromtogr., B: Anl. Technol. Biomed. Life Sci. 1998, 707, Mngus, A.; Atemnkeng, E. M.; Jcqueline, P.; J. Phrm. Biomed. Anl. 2007, 43, Petruci, J. F. S.; Crdoso, A. A.; Pereir, E. A.; Quim. ov 2011, 34, ICH Q2 (R1); Vlidtion of Anlyticl Procedures: Text nd Methodology, Interntionl Conference on Hrmoniztion, ICH Q1A (R2); Stbility Testing of new Drug Substnces nd Products, Interntionl Conference on Hrmoniztion, 2003.
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