QUANTITATIVE DETERMINATION OF ACETAMINOPHEN, PHENYLEPHRINE AND CARBINOXAMINE IN TABLETS BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY
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1 Quim. Nov, Vol. 32, No. 7, , 2009 QUANTITATIVE DETERMINATIN F ACETAMINPHEN, PHENYLEPHRINE AND CARBINXAMINE IN TABLETS BY HIGH-PERFRMANCE LIQUID CHRMATGRAPHY Crin de A. Bstos e Mrcone A. L. de liveir* Deprtmento de Químic, Universidde Federl de Juiz de For, Juiz de For - MG, Brsil Recebido em 30/9/08; ceito em 27/3/09; publicdo n web em 10/8/09 Not Técnic An lterntive methodology for nlysis of cetminophen (Ace), phenylephrine (Phe) nd crbinoxmine (Cr) in tblets by ion-pir reversed phse high performnce liquid chromtogrphy ws vlidted. The phrmceuticl preprtions were nlyzed by using C18 column (5 µm, 300 mm, 3.9 mm) nd mobile phse consisting of 60% methnol nd 40% potssium monobsic phosphte queous solution (62.46 mmol L -1 ) dded with 1 ml phosphoric cid, 0.50 ml triethylmine nd 0.25 g sodium luryl sulfte. Isocrtic nlysis ws performed under direct UV detection t 220 nm for Phe nd Cr nd t 300 nm for Ace within 5 min. Keywords: cetminophen; phenylephrine; crbinoxmine. INTRDUCTIN Common colds re virl disese cused minly by rhinovirus nd coronvirus, consisting of n cute infection of the upper respirtory system mucos. Infection occurs minly through direct contct nd rrely through sputter, sneezing nd cough. Infected people spred the etiologic gent by respirtory secretion such s nsl mucus, which infects hnds nd objects. The common cold is normlly hrmless nd generlly disppers within one or two weeks unless secondry bcteril infection is dignosed. nce no specific tretment cn be given, the usul procedure consists of lleviting the symptoms. The symptomtic tretment is bsed on the prescription of drugs tht llevite the nsl congestion, dry the mucous membrnes nd reduce both temperture nd pin. This is chieved through drug combintion since no single drugs cn hve ll these effects. The phrmceuticl ssocition is often used s they offer more convenient tretment thn single ones. 1 Some drugs currently vilble combine three phrmceuticls: cetminophen (Ace), n nlgesic nd ntipyretic; phenylephrine hydrochloride (Phe), nsl decongestnt; nd crbinoxmine mlete (Cr), n nti-histmine. Figure 1 shows the chemicl structure for the three compounds. Among the clssicl nlyticl methodologies used for nlysing these phrmceuticls re: titrimetry, 2 spectrometry UV-Visible, 2,3 cpillry electrophoresis 4-6 nd high performnce liquid chromtogrphy (HPLC) H pk 10.1 Cl H pk 8.9 H N CH3. HCl Figure 1. Chemicl structure of Ace, Phe nd Cr *e-mil: mrcone.oliveir@ufjf.edu.br N CH 3 H N. CH 3 pk 8.7 Phenylephrine hydrochoride (Phe) Crbinoxmine mlete (Cr) pk 9.5 H H N H Acetminophen (Ace) CH 3 As regrds HPLC methodologies, Brbs et l. 16 developed method for the determintion of cetminophen, phenylephrine hydrochloride nd chlorphenirmine mlete using two cynopropyl columns, constnt proportion of queous orgnic solvent (95:5, v/v) under grdient of ph from 7.5 to 2.0 with nlysis time of 14 min. Shervington et l. 18 optimized method for the determintion of cetminophen nd five of its substituted derivtives by reversed phse chromtogrphy system in isocrtic mode using mobile phse constituted of wter nd cetonitrile (70:30, v/v). Erk et l. 13 proposed n lterntive methodology for determining chorphenirmine mlete nd phenylephrine hydrochloride using UV detection t 269 nm nd reversed phse in isocrtic mode. Lu nd Mok 14 developed method for the determintion of eight ctive ingredients in cough-cold syrups, including phenylephrine hydrochloride, using cyno column nd wter, cetonitrile nd ethnol (36:60:2) contining 1 mmol L -1 perchloric cid s the mobile phse within 22 min. To our knowledge, the methods described in the literture do not cover the nlysis of the ssocition Ace/ Phe nd Cr/Ace. Therefore, the min contribution of this work ws to develop single seprtion method for nlyzing two different phrmceuticl ssocitions. This method cn lso be used s tool in the qulity control process of phrmceuticl industry or s n lterntive nlyticl monitoring procedure, which cn be used by the supervisory gencies such s Agênci Ncionl de Vigilânci Snitári (ANVISA). Within this context, simple lterntive methodology for determintion of these drugs in tblets using n isocrtic chromtogrphic mode in nlysis time of 5 min ws proposed. After prmeter vlidtion, the method proved to be successful nd ws pplied to the nlysis of commercil products contining these ctive ingredients. EXPERIMENTAL Mteril Regents nd chemicls Methnol ws of chromtogrphic grde nd ll other chemicls were of nlyticl grde. Phosphoric cid, potssium phosphte monobsic, methnol, ethnol, triethylmine nd sodium luryl sulfte were purchsed from Vetec (Rio de Jneiro, RJ, Brzil). Wter ws purified with Milli-Q, Milipore System. All solvents nd solutions were filtered through 0.45 µm millipore filter (Milipore millex-hv filter units) (São Pulo, SP, Brzil).
2 1952 Bstos e liveir Quim. Nov The following excipients were purchsed from Medquímic (Juiz de For, MG, Brzil): pregeltinized strch, povidone, steric cid, microcrystlline cellulose 102, glycolte strch sodium, opdry II 85F19193 trnslucent, titnium dioxide nd 10 yellow dye lcquer (commercil product 1) nd pregeltinized strch, povidone, steric cid, microcrystlline cellulose 102, opdry II 85F19193 trnslucent, titnium dioxide nd yellow dye lcquer 06 (commercil product 2). Phenylephrine hydrochloride (Phe) (99.9%) nd crbinoxmine mlete (Cr) (100.0%) were purchsed from Americn Phrmcopoei (Rockville, MD, USA). Acetminophen (Ace) (99.8%) ws purchsed from Brzilin Phrmcopoei (Rio de Jneiro, RJ, Brzil). Smples Twenty tblets of commercil product 1 (CP1) (20.0 mg Phe nd mg Ace) nd commercil product 2 (CP2) (4.0 mg Cr nd mg Ace) were purchsed from locl phrmcies (Juiz de For, MG, Brzil). Instrumenttion HPLC system: The experiments were performed in high performnce liquid chromtogrphy model Wters 1525 (Milford, (MA), USA) equipped with photo diode rry detector model 2996, temperture control device mintined t 27 C nd dt cquisition nd tretment softwre (Empower Build 1154). Column: The nlyticl column ws reversed phse Lun Phenomenex C18 (5 μm, 300 mm x 3.9 mm) (Torrnce, CA, USA). Methods Smple preprtions Twenty tblets of CP1 nd CP2 purchsed from locl phrmcies were seprtely weighed nd ground to homogeneously fine powders. The powder corresponding to CP1 (20.0 mg Phe nd mg Ace) nd CP2 (4.0 mg Cr nd mg Ace) were weighed nd dissolved with ml of mobile phse in seprte volumetric flsk. Five ml of these solutions were diluted gin with mobile phse in nother 50 ml volumetric flsk nd filtered through 0.45 µm millipore filter in order to obtin cler solutions. Chromtogrphic conditions All nlyses were performed t room temperture (bout 25 C) under isocrtic conditions. A mobile phse consisted of 60% methnol nd 40% potssium monobsic phosphte queous solution (62.46 mmol L -1 ) dded with 1.0 ml phosphoric cid, 0.50 ml triethylmine nd 0.25 g sodium luryl sulfte (ph of the whole mixture equl 4.10). Flow rte ws 1.0 ml min -1 nd volume injection ws 50 μl. The UV detection ws set t 220 for Cr nd Phe nd t 300 nm for Ace. At the beginning of the dy, mobile phse ws pumped through the HPLC system during 30 min until chieving bseline stbility. Wvelength selection The wvelength selection ws bsed on UV-Visible spectr obtined for ech compound by mens of diode rry detector in HPLC system. The wvelengths were selected t 220 for Phe nd Cr nd t 300 nm for Ace (Ace t 220 nm present offset pek signl sturted), s the three compounds presented cceptble pek signl for smple nlysis in these wvelengths. Stndrd solution preprtion Accurtely weighed mounts of stndrds of Cr nd Phe equivlent to 40.0 nd 50.0 mg were trnsferred to seprte volumetric flsks contining volume of (solution 1) nd 50.0 (solution 2) ml, respectively; 40.0 mg of Ace ccurtely weighed were trnsferred to volumetric flsk of ml contining 1.0 ml of the solution 1 nd 2.0 ml of the solution 2, forming the stndrd solution. All volumes were completed with mobile phse. Finl concentrtions were 4.0, 20.0 nd mg L -1 for Cr, Phe nd Ace, respectively. Stndrd solution ws filtered through 0.45 µm millipore filter nd diluted with mobile phse in order to obtin cler solutions. Clibrtion curves The following concentrtions levels for: Cr (3.2, 3.6, 4.0, 4.4 nd 4.8 mg L -1 ); Phe (16.0, 18.0, 20.0, 22.0, 24.0 mg L -1 ) nd Ace (320.0, 360.0, 400.0, 440.0, mg L -1 ) were obtined from ech stndrd solution, conveniently diluted with mobile phse in presence of the excipients. Ech solution ws injected in the chromtogrphic system (n=3) nd men vlues of pek res were plotted ginst concentrtion. The curves were fitted by liner regression with lest men squre method. RESULTS AND DISCUSSIN Preliminry study In order to investigte the method for drug nlysis in phrmceuticl formultions, preliminry tests were performed to select optiml conditions. Prmeters such s detection wvelength, idel mobile phse nd their proportions, optimum ph nd stndrd solution concentrtion were exhustively studied. Severl binry or ternry eluents were tested using different proportions of solvent, such s cetonitrile, methnol nd wter. However, stisfctory results were chieved through the ion-pir reversed phse liquid chromtogrphy (IRPLC) using sodium luryl sulfte s ionic pir regent. IRPLC ws investigted s n lterntive, bsed on the work described in the Americn Phrmcopei for chlorphenirmine mlete nlysis ssocited with phenylpropnolmine hydrochloride. 7 In the present cse, potssium phosphte monobsic nd phosphoric cid were used for ph djustment ( 4.10) nd to promote ionic pir formtion of the bsic solutes with the counter ion. Methnol ws used s n orgnic modifier nd triethylmine ws employed to reduce the tiling fctor of the bsic solutes, cused by the interction between these compounds nd the free silnol groups in the C18 surfce column. Figure 2 shows the chromtogrm for stndrd mixture obtined through the optimized vribles in ccordnce with the fetures described bove. The bseline seprtion of stndrd mixture through isocrtic mode within 5 min ws chieved. The smple loop size ws set t 50 µl in order to optimize the Cr signl, which ws in concentrtion much smller thn Ace in the smple. Mobile phse flow ws djusted t 1.0 ml min -1 in order to mintin pressure within the cceptble limit of the chromtogrphic system. Tble 1 shows nlyticl prmeters such s resolution (R), efficiency (N), symmetry (A/B), nd reltive retention (α) obtined for the optiml conditions. Vlidtion procedures After djusting the chromtogrphy conditions, some vlidtion prmeters for CP1 nd CP2, such s selectivity, linerity, precision, limit of detection (LD), limit of quntifiction (LQ), ccurcy nd robustness, were determined, s Resolution ANVISA RE n o 899, of 29/05/ Selectivity nd linerity Method selectivity ws ssessed by the pek purity test (comprison between nlyte pek nd uto threshold in the purity plot)
3 Vol. 32, No. 7 Quntittive determintion of cetminophen, phenylephrine nd crbinoxmine 1953 Tble 2. Sttisticl results obtined from linerity clcultion (stndrds + phrmceuticl excipients) Ace (±74.76) Phe (±736.05) Ace b (±136.33) Cr b (± ) Slope Intercept r p-vlue c (±29897) (±15009) (±54791) (±11480) Commercil product 1, b commercil product 2, c Shpiro-Wilk Normlity Test Figure 2. Chromtogrms for stndrd mixture of (1) Cr, 4.0 mg L -1 ; (2) Ace, mg L -1 ; nd (3) Phe, 20.0 mg L -1 using photo diode rry detector set t 220 nd 300 nm. pertionl conditions s indicted in the experimentl prt Tble 1. Anlyticl prmeters such s resolution (R), efficiency (N), symmetry (A/B), nd reltive retention (α) obtined for the developed method R c Ace Phe Ace b Cr b 7.0* 3.5* 7.0** 3.5** α c 3.2* 3.1* 3.2** 3.1** A/B c 1.4 ** 1.3 ** 1.3 ** 1.4 ** 1.4 * 1.2 * 1.3 * 1.4 * N c 2965* 4550* 3006* 2644* 2911** 4325** 2992** 2673** Commercil product 1, commercil product 2, c Men (n=6), *Stndrds; **stndrds + phrmceuticl excipients using diode rry detector. The nlyte chromtogrphic pek ws not found to be ttributble to more thn one component. 19,20 Linerity ws evluted tking into ccount the correltion coefficient (r). The correltion coefficient equl to or higher thn 0.99 is considered evidence of idel dt fitting to line regression performed through lest-squre tretment. 19 In order to evlute lck of fit of the regression, Shpiro-Wilk Normlity Test ws performed for the residues. 21 As the p-vlue clculted ws higher thn 0.05, the residue distribution is considered norml nd the model is liner within the rnge evluted (Tble 2). Precision, limit of detection (LD) nd limit of quntifiction (LQ) Precision cn be determined through the estimte of the reltive stndrd devition (RSD). 19 The precision in the vlidtion of this optimized method ws performed t two levels: repetbility nd intermedite precision. Repetbility (n=6) in smple re ws crried out for 100.0% of the test concentrtion. In the present cse, concentrtions t 4.0, 20.0 nd mg L -1 for Cr, Phe nd Ace, respectively were used. Intermedite precision (n=6) ws performed on different dys. All results presented cceptble precision vlues (not exceeding 5.00%) 19 s shown in Tble 3. LD nd LQ were clculted by mens of the stndrd devition rtio of the intercept of three clibrtion curves obtined from linerity by mens of the slopes of the respective curves multiplied by 3 nd 10, respectively. 19 LD nd LQ obtined presented cceptble vlues for smple nlysis s presented in Tble 3. Tble 3. RSD (%) in concentrtion found for smples obtined from repetbility nd intermedite precision. LD nd LQ vlues (mg L -1 ) Accurcy Accurcy, in the present cse, ws clculted s the percentge of recovery by the ssy of the known dded mount of nlyte in the smple. 19,20 Thus, recovery tests were performed by dding known mounts of stndrd in the smple t five levels of concentrtions for ech drug, s shown in Tble 5. For ccurcy test, men recovery percentge (R%) ws ± 2.0% nd single R% concentrtion ws ± 5.0% (Tble 4). The results obtined show tht the method presents cceptble ccurcy. Robustness Ace Phe Ace b Cr b Repetbility c 0.56* 0.64* 0.04* 0.24* 0.07** 0.14** 0.07** 0.31** Intermedite 2.31* 0.83* 0.49* 1.10* precision c 1.72** 1.37** 0.52** 0.24** LD 12.50** 0.36** 20.95** 0.99** LQ 41.69** 1.18** 69.86** 3.10** Commercil product 1, b commercil product 2, c Men (n=6), *Stndrds; **stndrds + phrmceuticl excipients The robustness ws evluted by intentionl minor modifictions in the chromtogrphic conditions in the proposed methodology. 19 Within this context, the prmeters selected to evlute robustness
4 1954 Bstos e liveir Quim. Nov Tble 4. Recovery dt of stndrd solutions dded to the smples nlyzed using the proposed HPLC method Ace Phe Ace b Cr b Added mount (mg) Found mount c Recovery (%) ± ± ± ± ± d ± ± ± ± ± d ± ± ± ± ± d ± ± 0, ± ± ± were: mobile phse, flow rte nd ph. Tble 6 shows the experiments performed for robustness evlution. It is importnt to remember tht for commercil product 1 the mximum flow rte ws set t 1.0 ml min -1 in order to mintin pressure lower thn 3000 psi. All prmeters were performed in six replictes. For the robustness test, the recovery chieved remined within the intervl of ± 5.0% s shown in Tble 5. Therefore, little vritions in the chromtogrphic prmeters 99 d Commercil product 1, b commercil product 2, c Men (n=3); d men of recovery rnge such s mobile phse, flow rte nd ph were found to be cceptble vlues in reltion to the reference vlue. Quntittive determintion in phrmceuticl preprtions purchsed from locl phrmcies After evluting some vlidtion prmeters, the optimized method ws pplied to the smple nlysis obtining 19.9 mg (± 7.1 x10-2 %) of Phe nd 396,1 mg (± 4.0 x10-3 %) of Ace for CP1 nd 3,9 mg (± 1.8 x 10-1 %) of Cr nd 402,4 mg (± 9.0 x 10-2 %) of Ace for CP2 s results. Figure 3 shows the chromtogrms obtined to smples nlyzed. Figure 3. Chromtogrms obtined for smple nlysis: (A) - commercil product 1 nd (B) - commercil product 2. pertionl conditions s indicted in the experimentl prt CNCLUSINS The simultneous seprtion of Ace, Phe nd Cr by isocrtic ion-pir reversed phse liquid chromtogrphy hs been chieved. All vlidtion prmeters of the method optimized hve obeyed the vrition limits permitted. Therefore, the vlidted method cn be useful for qulity ssurnce in the phrmceuticl industry of these preprtions, presenting simple mobile phse system, short nlysis Tble 5. Robustness results for commercil product 1 nd 2 clculted s the percentge of recovery Experiments Ace Phe Ace b Cr b A c B c C c D c E c F c G c Mobile phse (%MeH): (-) 55; (0) 60; (+) 65; 2- Flow (ml min -1 ): (-) 0.7; (0) 1.0; (+) 0.4 / 1.3 b ; 3- ph: (-) 3.1; (0) 4.1; (+) 5.1. Commercil product 1, b commercil product 2, c Men (n=6)
5 Vol. 32, No. 7 Quntittive determintion of cetminophen, phenylephrine nd crbinoxmine 1955 time, nd simple step of smple preprtion s dvntges in comprison with the methods described in the literture. ACKNWLEDGMENTS The uthors wish to cknowledge the Medquímic Indústri Frmcêutic Ltd, Coordenção de Aperfeiçomento de Pessol de Nível Superior (CAPES), Conselho Ncionl de Desenvolvimento Científico e Tecnológico (CNPq / nd /2008-2) nd Fundção de Ampro à Pesquis do Estdo de Mins Geris of Brzil (FAPEMIG CEX-APQ nd CEX-APQ 01837/08) for fellowships nd finncil support. REFERENCES 1. Korolkovs, A.: Frnç, F. F. A. C.; Dicionário Terpêutico Gunbr, 15 th ed., Gunbr Koogn S.A.: Rio de Jneiro, Brzilin Phrmcopei, 3 rd ed., Andrei: São Pulo, Brzilin Phrmcopei, 4 th ed., Atheneu: São Pulo, Mrin, A.; Brbs, C.; J. Phrm. Biomed. Anl. 2004, 35, Mrchesini, A. F.; Williner, M. R.; Mntovni, V. E.; Robles, J. C.; Goicoeche, H. C.; J. Phrm. Biomed. Anl. 2003, 31, kmoto, H.; Nkjim, T.; Ito, Y.; Aketo, T.; Shimd, K.; Ymto, S.; J. Phrm. Biomed. Anl. 2005, 37, United Sttes Phrmcopei, 29 th ed., United Sttes Phrmcopeil Convention: Rockville, Mrín, A.; Grcí, E.; Grcí, A.; Brbs, C.; J. Phrm. Biomed. Anl. 2002, 29, Rvisnkr, S.; Vsudevn, M.; Gndhimthi, M.; Suresh B.; Tlnt 1998, 46, Mrín, A.; Espd, A.; Vidl, P.; Brbs, C.; Anl. Chem. 2005, 77, Gil-Agustí, M.; Grci-Alvrez-Coque, M. C.; Esteve-Romero, J.; Anl. Chim. Act 2000, 421, Qi, M.; Wng, P.; Chen, J.; Chromtogrphi 2004, 60, Erk, N.; Krtl, M.; Ιl Fármco 1998, 53, Lu,.; Mok, C.; J. Chromtogr., A 1995, 693, Grcí, A.; Rupérez, F. J.; Mrín, A.; Mz, A. D. L.; Brbs, C.; J. Chromtogr., B 2003, 785, lmo, B.; Grcí, A.; Mrín, A.; Brbs, C.; J. Chromtogr., B 2005, 817, Gumbhir, K.; Mson, W. D.; J. Phrm. Biomed. Anl. 1996, 14, Shervington, L. A.; Skhnini, N.; J. Phrm. Biomed. Anl. 2000, 24, Agênci Ncionl de Vigilânci Snitári (ANVISA); Resolução RE n o 899, de 29/05/ Interntionl Conference Hrmonistion (ICH); Vlidtion of Anlyticl Procedures: Methodology, Q2B (CPMP/ICH/281/95), Montgomery, D. C.; Design nd Anlysis of Experiments, 6 th ed., Wiley, 2005.
Keywords: Acetaminophen. Phenylephrine. Tablets. Dissolution. HPLC.
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