Artigo. Quim. Nova, Vol. 35, No. 5, , 2012
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1 Quim. ov, Vol. 35, o. 5, , 2012 IMULTAEU DETERMIATI F -TERIDAL ATI-IFLAMMATRY DRUG I PHARMACEUTICAL FRMULATI AD HUMA ERUM BY REVERED PHAE HIGH PERFRMACE LIQUID CHRMATGRAPHY Muhmmd wz Deprtment of Chemistry, University of Krchi, Krchi-75270, Pkistn Recebido em 8/7/11; ceito em 29/11/11; publicdo n web em 23/1/12 Artigo A rpid nd sensitive method using high performnce liquid chromtogrphy hs been developed nd vlidted for the simultneous determintion of non-steroidl nti-inflmmtory drugs (AIDs) in phrmceuticl formultions nd humn serum. ix AIDs including: nproxen sodium, diclofenc sodium, meloxicm, flurbiprofen, tiprofenic nd mefenmic cid were nlyzed simultneously in presence of ibuprofen s internl stndrd on Mediterrne C 18 (5 µm, 250 x 0.46 mm) column. Mobile phse comprised of methnol: cetonitrile: H 2 (60:20:20, v/v; ph 3.35) nd pumped t flow rte of 1 ml min -1 using 265 nm UV detection. The method ws liner over concentrtion rnge of μg ml -1 (r 2 = ). Keywords: AIDs; serum; reversed phse high performnce liquid chromtogrphy. ITRDUCTI on-steroidl nti-inflmmtory drugs (AIDs) (Figure 1) hve nlgesics, ntipyretics nd nti-inflmmtory ctivities nd re widely used in the tretment of cute nd chronic pin, osteorthritis, rheumtoid rthritis nd relted conditions. The phrmcologicl ctions of AIDs re relted to inhibition of cyclooxygense (CX), H H e-mil: nwwz@gmil.com H H H 3 C CH F 3 H Mefenmic cid H Tiprofenic cid CH 3 Ibuprofen (internl stndrd) H H Cl Cl Diclofenc proxen Figure 1. Chemicl structures of non-steroidl nti-inflmmtory drugs H H H key enzyme of prostglndin biosynthesis t the site of inflmmtion. The simultneous mesurement of these AIDs concentrtions in biologicl smples is required in clinicl nd toxicologicl screening, phrmcokinetic studies, s well s in therpeutic monitoring. Furthermore, it is lso very importnt to precisely quntify these AIDs in phrmceuticl formultions for qulity control. 1 Until now, vriety of chromtogrphic methods hve been proposed for the determintion of AIDs in phrmceuticl formultions nd biologicl fluids, by gs chromtogrphy, 2-4 spectrofluorometry, 5 high performnce liquid chromtogrphy 6-17 nd cpillry electrophoresis. 18 Generlly, it is impossible tht one ptient would be prescribed for more thn one kind of AIDs t the sme time; however simultneous determintion of these drugs is useful in phrmceuticl routine nlysis nd biologicl smples. This pper reports the simultneous determintion of AIDs in phrmceuticl formultions nd humn serum. It is precise, ccurte nd rpid method. EXPERIMETAL Mterils nd regents Pure tiprofenic cid ws obtined from Aventis Phrm (Pvt) Ltd, meloxicm from AGP (Pvt) Ltd, diclofenc sodium, flurbiprofen, ibuprofen nd nproxen sodium from Phrmevo (Pvt) Ltd. Dosges form of Tiprofenic cid (urgm 300 mg) diclofenc sodium (Voltrl 50 mg) flurbiprofen (ynlgo 100 mg), meloxicm (Melfx 15 mg) nd mefenmic cid (Ponstn 250 mg) were purchsed from locl mrket. Methnol nd cetonitrile (nlyticl grde) were purchsed from Tedi, UA. Deionized wter ws used to prepre mobile phse. Instrumenttion nd chromtogrphic conditions The development of the method nd vlidtion of the work ws performed on liquid chromtogrphic system consisting of himdzu model LC-10AT VP pump with PD-10AT VP, vrible wvelength UV-Visible detector. Chromtogrphic system ws integrted vi himdzu model CBM-102 Communiction Bus Module
2 940 wz Quim. ov to Pentium-4 PC. Anlysis ws conducted on Mediterrne C18 (Teknokrom, Krchi, Pkistn) (5 µm, 250 x 0.46 mm) column, mobile phse consisted of methnol: cetonitrile: H 2 (60:20:20, v/v) nd ph ws djusted to 3.35 (pprent ph) with orthophosphoric cid. Mobile phse ws filtered dily using 0.45 µm membrne filter (Millipore, Germny) nd degssed in n ultrsonic bth. The smples were introduced through rheodyne injector vlve with 20-mL smple loop. Assys were performed t mbient temperture t flow rte of 1 ml min -1 nd detection t 265 nm. Preprtion of stndrd solutions tndrd solution of non-steroidl nti-inflmmtory drugs nd internl stndrd (100 μg ml 1 ) were prepred by dissolving them in methnol. Internl stndrd solution ws further diluted with methnol to give concentrtion 50 μg ml 1. Preprtion of clibrtion curves Approprite dilution of stndrd solution (100 μg ml 1 ) of nonsteroidl nti-inflmmtory drugs were mde using methnol to obtin solution of concentrtion of 0.25, 1.0, 2.50, 5.0, 12.50, 25.0 nd 50.0 μg ml 1. A correltion between pek re nd concentrtion μg ml 1 of non-steroidl nti-inflmmtory drugs were estblished nd clibrtion curves were obtined. Limit of detection nd quntifiction (LD nd LQ) The limit of detection is the lowest quntity of nlyte in ny smple which cn be detected but cnnot be quntified where s the quntittion limit of ny nlyticl procedure is the lowest mount of nlyte in smple which cn be quntittively nlyzed with suitble precision nd ccurcy. The eqution used to clculte LD nd LQ re: LD = 3.3ơ/ nd LQ =10ơ/ ơ = stndrd devition of the lowest stndrd concentrtion, = slope of the stndrd curve. Precision nd ccurcy The precision of proposed method ws evluted through intr-dy (repetbility) nd inter-dy (intermedite precision) t concentrtion of 0.25, 2.50 nd μg ml 1. Three replictes were mde for intr- nd inter-dy study. The precision is expressed s percentge reltive stndrd devition (% RD). To evlute the ccurcy of the proposed method, recovery tests for ll nlytes were performed by dding known mounts of stndrd solutions to smples followed by nlysis using proposed method. Accurcy ws expressed s percen tge recovery nd determined t three concentrtion levels (0.25, 2.50 nd μg ml 1 ). Three replictes were mde for ccurcy study. electivity The selectivity of the method ws evluted by nlyzing blnk drug-free serum smples obtined from helthy volunteer nd spiked serum smples. The probble interferences from endogenous substnces were ssessed by observing the chromtogrms of blnk nd spiked serum smples. on-steroidl nti-inflmmtory drugs phrmceuticl formultions were lso nlyzed nd compred with the stndrd chromtogrms of drugs for excipients interference. Dosge nlysis The contents of 20 tblets of tiprofenic cid (urgm 300 mg) diclofenc sodium (Voltrl 50 mg) flurbiprofen (ynlgo 100 mg), meloxicm (Melfx 15 mg) nd mefenmic cid (Ponstn 250 mg) were weighed nd finely grounded. A mss of powder equivlent to the verge mss of tblet ws trnsferred to volumetric flsks with methnol. olutions were sonicted in ultrsonic bth for 10 min nd then diluted to volume with methnol. These primry stock solutions were filtered through Whtmn filter pper nd the filtrtes were further diluted suitbly to prepre secondry stock solution. Aliquots of the secondry stock solution were diluted to concentrtion of 0.25, 2.50 nd μg ml 1 nd the smples were nlyzed using bove mentioned chromtogrphic conditions. erum drug nlysis The recoveries of non-steroidl nti-inflmmtory drugs from pooled humn serum were determined by the stted chromtogrphic conditions. Multiple blood smples (10 ml) of 15 helthy non-smoker volunteers (ge rnging from yers), not tking ny other medicments were collected in glss tubes. 10 ml of cetonitrile ws then dded to ech serum smples to precipitte the proteins. After 15 min of centrifugtion t 3000 rpm, ll the upper lyers from the serum smples were put together to receive representtive pool of humn serum smples. This pool of serum smples ws mixed with AIDs nd internl stndrd in 1:1:1 rtio, filtered nd nlyzed. 19,20 REULT AD DICUI Isocrtic-mode of HPLC with UV detection ws developed for the determintion of non-steroidl nti-inflmmtory drugs in phrmceuticl formultions nd in humn serum. erum deproteintion for the determintion of drugs is commonly ccepted s the simplest methods s compred liquid-liquid extrction or solid-phse extrction from plsm smples nd usully hve high reproducibility. ptimiztion of chromtogrphic conditions In order to chieve suitble seprtion of nlytes from endogenous compounds of serum mtrix, the isocrtic elution mode ws chosen. The method ws optimized by vrition in ph of the mobile phse nd the percentge nd nture of the orgnic modifier (cetonitrile or methnol). Firstly, n ttempt ws mde regrding the composition of the mobile phse nd ph. Proportions of wter higher thn 20% gve rise to chromtogrphic signls which suffered mjor frontings. Higher percentge of methnol thn 60% results in long retention time nd 20% of cetonitrile ws found suitble in mobile phse. When percentge of cetonitrile ws incresed in mobile phse peks were emerged. Chromtogrphic peks obtined t ph 3.35 were shrp (Figure 2) thn those observed t ph 4 nd lso bsorbnce of endogenous components of serum ws lower t ph 3.35 (Figure 3 nd 3b). o mobile phse consisting of methnol:cetonitrile:h 2 (60:20:20, v/v) nd ph 3.35 ws optiml for the seprtion of non- -steroidl nti-inflmmtory drugs nd it provides high sensitivity. The system suitbility ws performed by studying the prmeters which include column efficiency or theoreticl pltes (), resolution (R), pek symmetry or tiling fctor (A ) nd cpcity fctor (k). The low vlue of pek symmetry or tiling fctor nd high vlues of column efficiency or theoreticl pltes, resolution nd cpcity fctor indicted the suitbility nd proper selection of mobile phse. These prmeters re presented in Tble 1.
3 Vol. 35, o. 5 imultneous determintion of non-steroidl nti-inflmmtory drugs 941 Figure 2. Chromtogrm of non-steroidl nti-inflmmtory drugs in the presence of ibuprofen s internl stndrd: (1) tiprofenic cid, (2) meloxicm, (3) nproxen sodium, (4) flurbiprofen, (5) diclofenc sodium, (6) ibuprofen, (7) mefenmic cid Tble 1. Chromtogrphic dt for seprtion of AIDs on Mediterrne C 18 column under the optimum seprtion conditions Anlytes K As b c Rs d Tiprofenic proxen Diclofenc Mefenmic cpcity fctor; b pek symmetry; c number of theoreticl pltes, d resolution Method development nd vlidtion ws crried out ccording to ICH vlidtion guidelines. 21 Linerity nd sensitivity The linerity of the method ws evluted by injecting six replicte of different concentrtions. Linerity ws observed in the concentrtion rnge of μg ml 1. For the determintion of linerity, stndrd clibrtion curve ws used. The sttisticl results of the linerity, LD nd LQ vlues re given in Tble 2. Precision nd ccurcy The precision ws expressed s percentge reltive stndrd devition (% RD) nd it rnged in % nd % for Figure 3. Chromtogrms of: () drug-free humn serum; (b) non-steroidl nti-inflmmtory drugs spiked in humn serum: (1) serum peks, (2) tiprofenic cid, (3) meloxicm, (4) nproxen sodium, (5) flurbiprofen, (6) diclofenc sodium, (7) ibuprofen, (8) mefenmic cid intr- nd inter-dy respectively in phrmceuticl formultions while in serum it ws less thn 3% (Tble 3). Accurcy ws expressed s percentge recovery nd it ws determined t three concentrtion levels. Three replictes were mde for ccurcy study, intr- nd inter-dy percentge recoveries from phrmceuticl formultions rnged in % nd %, respectively. Recoveries from humn serum rnged in % (Tble 4). electivity The chromtogrms obtined from blnk, spiked serum smples nd phrmceuticl formultions were identicl with tht obtined chromtogrm from stndrd solution of AIDs. There ws no pek Tble 2. Clibrtion curves nd limit of detection nd quntifiction of non-steroidl nti-inflmmtory drugs in phrmceuticl formultions Anlytes Concentrtion rnge Regression eqution r 2 LD b LQ c Tiprofenic y = x y =681.90x proxen y = x y = x Diclofenc y = x Mefenmic y = x Correltion of coefficient, b limit of detection (/=3), c limit of quntifiction (/=10)
4 942 wz Quim. ov Tble 3. Accurcy nd precision of non-steroidl nti-inflmmtory drugs in phrmceuticl formultions Conc. dded Tiprofenic Intr-dy Inter-dy RD% b % Rec. c RD% % Rec Diclofenc sodium Mefenmic cid proxen Concentrtion, b reltive stndrd devition, c % recovery Tble 4. Accurcy nd precision of non-steroidl nti-inflmmtory drugs in humn serum Conc. dded Tiprofenic % recovery Intr-dy RD% Precision Inter-dy RD% Diclofenc Mefenmic proxen observed when the nlysis of plcebo solution of AIDs were done. In ddition, pek purity index of ll nlytes were investigted nd found to be > Thus method demonstrted good resolution nd found to be free of interferences. Ruggedness Method ruggedness ws evluted by two nlysts performing ssy on seprte lots of non-steroidl nti-inflmmtory drugs. Ech nlyst prepred smples in triplicte nd used seprte instruments, regents, diluent nd mobile phse solutions. Reltive stndrd devition (n = 3) of for ll of the smples for ech lot ws less thn 2.0% indicting cceptble robustness. The method did not show ny notble devition in results from cceptble limits. CCLUI The proposed method using reversed phse high performnce liquid chromtogrphy ws found to be suitble for simultneous determintion of non-steroidl nti-inflmmtory drugs in phrmceuticl formultions nd humn serum. The detector response ws found to be liner over wide concentrtion rnge. Results re ccurte nd precise nd re confirmed by the sttisticl prmeters. The precision nd ccurcy of the method re well within the limits required for bionlyticl ssys. The lower limit of quntifiction permitted the use of the method for phrmcokinetic studies. ACKWLEDGEMET The uthor is thnkful to his fmily members for their finncil support.
5 Vol. 35, o. 5 imultneous determintion of non-steroidl nti-inflmmtory drugs 943 REFERECE 1. un, Y.; Tkb, K.; Kido, H.; kshim, M..; kshim K.; J. Phrm. Biomed. Anl. 2003, 30, Kim, K. R.; Yoon, H. R.; J. Chromtogr., B: Anl. Technol. Biomed. Life ci. 1996, 682, Wy, B. A.; Wilhite, T. R.; mith, C. H.; Lnde, M.; J. Clin. Lb. Anl. 1997, 11, El Hj, B. M.; Al Ainri, A. M.; Hssn, M. H.; Bin Khdem, R. K.; Mrzouq, M..; Forens. ci. Int. 1999, 105, Dmini, P. C.; Berzotti, M.; Cbezon, M. A.; J. Phm. Biomed. Anl. 2001, 25, Jedzinik, P.; zprengier-juszkiewicz, T.; Młgorzt,.; Żmudzki J.; Anl. Chim. Act 2010, 672, Aguilr-Arteg, K.; Rodriguez, J. A.; Mirnd, J. M.; Medin, J.; Brrdo, E.; Tlnt 2010, 80, Mdni, A. U.; Ahmd, M.; Akhtr,.; Usmn, M.; World Acd. ci. Engin. Technol. 2009, 55, Ibrhim, H.; Boyer, A.; Boujil, J.; Couderc, F.; epveu, F.; J. Chromtogr., B: Anl. Technol. Biomed Life ci. 2007, 857, Pnus, A.; Multri, A.; Incrnto, G.; Gnglirdi, L.; J. Phrm. Biomed. Anl. 2007, 43, Cnpro, R.; Muntoni, E.; Zr, G. P.; Dell, P. C.; Berno, E.; Cost, M.; Endi, M.; Biomed. Chromtogr. 2000, 14, Arcelloni, C.; Lnzi, R.; Pedercini,.; Molteni, G.; Fermo, I.; Pontiroli, A.; Proni, R.; J. Chromtogr., B: Anl. Technol. Biomed Life ci. 2001, 763, Mikmi, E.; Goto, T.; hno, T.; Mtsumoto, H.; Ingki, K.; Ishihr, H.; ishid, M.; J. Chromtogr., B: Anl. Technol. Biomed Life ci. 2000, 744, Mrtin, M. J.; Pblos, F.; Gonzlez, A. G.; Tlnt 1999, 49, Hiri, T.; Mtsumoto,.; Kishi, I.; J. Chromtogr., B: Anl. Technol. Biomed Life ci. 1997, 692, iops, I.; Mmzoridi, K.; J. Chromtogr., B: Anl. Technol. Biomed Life ci. 1994, 656, Kzemifrd, A. G.; Moore, D. E.; J. Chromtogr., B: Anl. Technol. Biomed Life ci. 1990, 533, Heitmeier,.; Blschke, G.; J. Chromtogr., B: Anl. Technol. Biomed Life ci. 1999, 721, Aryne, M..; ultn,.; wz, M.; J. Anl. Chem. 2008, 63, Aryne, M..; ultn,.; Agh, Z. M.; Frhn, A..; J. Chil. Chem. oc. 2010, 55, The Europen Agency for the Evlution of Medicl Products; ICH TopicQ2B ote for Guidnce on Vlidtion of Anlyticl Procedures: Methodology, GPMP/ICH/281/95, 1996.
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