Jin Hee Kim, Ah Yeon Park, Eun Ha Jung, Cheol-Woo Lee, Tae Ho Lee and Jeong-Rok Youm
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1 Printed in the Republic of Korea "/"-:5*$"- 4$*&/$& 5&$)/0-0(: Vol. 20, No. 4, , 2007 pe wx r j )1-$ w w x ½ Á Á wá Á kyá w w w Development of a rapid HPLC method for the determination of penciclovir in human plasma using a monolithic column and its application to a bioequivalence study Jin Hee Kim, Ah Yeon Park, Eun Ha Jung, Cheol-Woo Lee, Tae Ho Lee and Jeong-Rok Youm College of Pharmacy, Chung-Ang University, Seoul, , Korea (Received July 18, 2007bG Accepted July 26, 2007) : w x r j p(monolithic) e w š j m v(hplc)-xÿ w w w. x ODS e š xw p e w š, (ionpairing reagent) sodium dodecyl sulfate»(residual silanol group) sw triethylamine ƒw, w»» (gradient elution) w., r j ü t w j 4 ü k. y w, 0.1~5 µg/ml ü ƒ yw ùkü. w w 5 xw w ü y 1.36~8.55 %, 92.8~100.0 % š, 5 xw w 0.93~5.62 %, w 0.1 µg/ ml. w 24 w q j w x w, w x q» x w w q. Abstract: A simple and rapid HPLC method with fluorescence detection(fld) for quantitation of penciclovir in human plasma using a monolithic column was developed and validated. Penciclovir and ganciclovir(internal standard, I.S.) were separated on a Chromolith column RP-18e ( mm) with a mobile phase consisting of a mixture of (A) methanol/50 mm sodium phosphate buffer containing 200 mg/l sodium dodecyl sulfate (3/97, ph 2.5) and (B) methanol/50 mm sodium phosphate buffer containing 200 mg/l sodium dodecyl sulfate (50/50, ph 2.5) at a flow gradient of 1.6~4.0 ml/min. The retention times of penciclovir and internal standard were less than 4.0 min. Calibration curve was linear (R 2 =0.9994) over a concentration range of 0.1~5 µg/ml. Corresponding author Phone : +82-(0) , 5674 Fax : +82-(0) youmjr@cau.ac.kr 323
2 324 ½ Á Á wá Á kyá Intra-day precision, accuracy and inter-day precision were 1.36~8.55 %, 92.8~100.0 % and 0.93~5.62 %, respectively with a limit of quantitation at 0.1 µg/ml. The present HPLC-FLD method is sensitive, precise and accurate. The method described herein has been successfully used for the bioequivalence study of a famciclovir formulation product after oral administration to healthy Korean volunteers Key words : Penciclovir, HPLC-Fluorescence Detection, Monolithic column, Bioequivalence study, Plasma r j (penciclovir, 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3H-purin-6-one) prodrug q j (famciclovir) nucleoside yw (Fig. 1) ƒ. q j r j z, herpes simplex virus type I(HSV-I), type II(HSV-II), varicellazoster virus(vzv), Epstein-Bar virus(ebv) s thymidine kinase w monophosphate xk y. z sü z w r j triphosphate y dgtp DNA herpes virus DNA w k w. r j s (HSV) I, IIx (VZV) z. 1-3 w r j n w û, w» 4 w r j 6-deoxy diacetyl l yw q j n w e wš. w q j mg 1 z n w, š x (C max )ƒ 1.87 µg/ml, š x (T max ) 0.76 hr,» 3 hr, r j 90 % y š. 6 q j w 7-10 w r j š j m v(hplc) 11»(UVD) x Ÿ»(FLD) 15 w, capillary electrophoresis w 16 š.» w š j m v, w ƒ 0.2 µg/ml, w ww ƒ w ƒ š. wr nucleoside ƒ 17 r j xÿ ƒ, Schenkel 15 xÿ» w aqueous humor w 0.05 µg/ml w g. Capillary electrophoresis UVD w x 16 k, w ù, û w w. LC-ESI-MS/MS w r j w š 18. w k š,, ƒ šƒ ¾ w»ƒ. x r j, š ƒ w LC-MS/MS, w HPLC mw w y wš w. y ƒwš p e w, m e w Fig. 1. Chemical structures of penciclovir and ganciclovir (internal standard). Analytical Science & Technology
3 p e w x r j HPLC w w x 325 ƒ w. œ xk ƒ w t ƒ š w ùkü, x e û š w». x r j p e w y w š, w (validation) w. w, y HPLC-FLD w, 24 w w û q j x j 250 mg q 250 mg m w w w» w w x w. t t š w w x» x ww, x w sƒ w x - š l w x - š w (AUC t ) š x (C max ) yw z w w.»» r j t t Calbiochem (Darmstadt, Germany) l w, ü t w j ion-pairing reagent w sodium dodecyl sulfate Sigma (St. Louis, MO, USA) qt w.» sw» w ƒw triethylamine 21 Junsei chemical (Tokyo, Japan) l w. w m p, k, ùp Merck (Darmstadt, Germany) l HPLC w š, Fisher Scientific (Springfield, NJ, USA) HPLC w. w m p»k p 1 w. HPLC rv Waters 600E pump(waters, Milford, MA, USA), w autosampler Hitachi L-2200(Hitachi, Tokyo, Japan)», e Hitachi L-2300, xÿ» Jasco 821-FP(Jasco, Tokyo, Japan) w. HPLC e Chromolith column RP-18e(4.6Ü100 mm, Merck, Darmstadt, Germany) w, l e Autochro-2000(Ver. 1.0, Young Lin, Anyang, Korea) w. x Table 1. Gradient elution profile used for the separation of penciclovir in human plasma using a monolithic column Time (min) Flow rate (ml/min) Mobile phase A(%) Mobile phase B(%) )1-$ y w x r j š HPLC š 15 w y w z ww. x w. e Chromolith column RP-18e(4.6Ü100 mm) w, e y w stainless steel frit wx(0.5 µm) w. (A) 50 mm sodium phosphate buffer(ph 2.5, triethylamine 2 ml/l, sodium dodecyl sulfate 200 mg/l)/methanol=98/2, (B) 50 mm sodium phosphate buffer(ph 2.5, triethylamine 2 ml/l, sodium dodecyl sulfate 200 mg/l)/methanol=50/ µm membrane filter wš, q» ƒ w w, y gƒ»» w (Table 1). e 20 o C w w, xÿ»» q 254 nm, q 380 nm w w. t r j t t 1 mg/ml z þ jš, þ w blank x w r j x ƒ ƒƒ 0.1, 0.2, 0.5, 1, 2, 4, 5 µg/ml ƒ t x. ƒƒ t x 0.5 ml x š,» ü t j (10 µg/ml ) 50 µl ƒwš k y w» 10 yww.» m p 1 ml ƒw k yw» w z, w w. w Áò w x»š 40 o C» k z, 50 mm sodium phosphate buffer(ph 2.5, triethylamine 2 ml/l, sodium dodecyl sulfate 200 mg/ L)/Methanol = 98/2( A) 100 µl Vol. 20, No. 4, 2007
4 326 ½ Á Á wá Á kyá w. 10 µl w HPLC-FLD w,» ü t vj w r j vj ƒ š w. w x 5z ww ü x y w š, 5 x ww x w. vx vx t t š w w x» w 19~55 w û, y»,,, x,, ü x y š, x k wš œš w 36 w. x, x w ƒ, xü, w ü w š, wù w ù w. 36 vx»»» wwš» w w q 24 w, x ƒ z w x w. vx w n l x» ¾ w m sww w. w x»,,, xanthine w w w. x ú z 7 vx w w œw z, z 8 l x n z 4 ¾ g. vx x ü w w jš, z 10 ew w, x 7 w x w. n x n, x vx wù œ x w w. n 2» 2 t p x kw, 24 vx 12 ù. 1» 1 q 250 mg, 2 x j 250 mg n w, 2» n w. vx heparin-locked I.V. catheter ewš œ x 10 ml xw, 2 x ƒƒ ml wì n w. x n, n z 15, 30, 45, 1, 1.5, 2, 2.5, 3, 4, 6, 8, w. x I.V. catheter û xq w» w 1 ml x ü š 8 ml x heparinized vacutainer w. x z I.V. catheter w x š w» w xq 0.5 ml w. x x š wš x q» w, vacutainer š, ew 3000 rpm 10 w z, x w polypropylene x š ¾ w 70 o C w. x vx l ƒ w w 70 o C w x ew z 1 kw, 0.5 ml w x»š» ü t 50 µl ƒw z, w w. w HPLC w j m l ü t vj w r j vj wš, w w x r j w. q l q l AUC t, C max, T max HPLC w x - š l w. š x (C max ) š x (T max ) de l w š, n z x 10 ¾ x - š w (AUC t ) Õ œ w w. T max w AUC t C max ye w x m v K-BE Test α=0.05 w š, 90 % w w. q 250 mg w x j 250 mg w t t š w w x». Analytical Science & Technology
5 p e w x r j HPLC w w x 327 š x r j r j j (acyclovir)ù j nucleoside f». 22 C18 C8 e w š w ey, 95 % w w. w w» w 100 % x y e w ù, ƒw š ƒ j 15. w w r j ¼ w ù w x ƒ ~ w w w»ƒ. p e x e šƒ ù, š p w e û, j y š ƒ w, z» w. w Tzanavaras 19 p e w j šz w šw, Kazoka 20 purine pyrimidine Si- p e w šw. triethylamine(» sw» w) ƒw r j x ü w gš, w»» w r j 4 ü g. w vx œx œx r j ü t wì ƒw r j n w z 4 z w x x w z, HPLC w j m Fig. 2 ùkü. r j vj 3.8, ü t j vj 2.1, x w l w š yw. vx œx, œx ü t ƒ w 0.1, 0.2, 0.5, 1, 2, 4, 5 µg/ml t x ƒƒ w z HPLC w, x l w r j Fig. 2. Chromatograms of (A) blank plasma; (B) blank plasma spiked with penciclovir (1 µg/ml) and internal standard (ganciclovir); (C) plasma sample from a healthy volunteer at 4 hr after oral administration of 250 mg famciclovir tablet. y(r j /ü t vj ) =3.4633x(r j, µg/ml) (R 2 = ) 0.1~5 µg/ml w ùkü (Fig. 3). ƒ» 5 ƒ (0.1, 0.5, 1, 2, 5 µg/ml) r j t x w, (C.V., %) ü 1.36~8.55%, 0.93~5.62 % ùkûš, y 92.8~100.0 % ùkû (Table 2). x r j w (LOQ, limit of quantitation) j m y (S/N ratio) 10 w š 20 % w š, y 80~120 % w 0.1 µg/ml w. l x r j w HPLC Vol. 20, No. 4, 2007
6 328 ½ Á Á wá Á kyá Fig. 3. Calibration curve of penciclovir in human plasma(y = x , R 2 = ). Table 2. Precision and accuracy for the determination of penciclovir in human plasma by the HPLC-FLD method Concentration (g/ml) Precision C.V. a (%) Accuracy (%) Intra-Day (n=5) Inter-Day (n=5) Intra-Day (n=5) a : C.V. (Coefficient of Variation) = (S.D./mean) 100 w x w p,, y š y w. q j sƒ w 24 x j 250 mg q 250 mg ƒƒ 1 n w z, xwš w vx w r j s³ x - š Fig. 4 ùkü. ƒ vx AUC t n z 10 ¾ ƒ vx x - š l Õ œ w w. C max ƒ vx x - š l ƒ x w, T max ƒ vx x - š l š x w w. q 250 mg s³ x - š w AUC t (µg hr/ml) 2.88Û0.58, šx C max (µg/ml) 1.50Û0.33, š x T max (hr) 0.71Û0.26. wr x j 250 mg s³ x - š w AUC t (µg hr/ml) 3.11 Û0.73, š x C max (µg/ml) 1.60Û 0.33, š x T max (hr) 0.68Û 0.33 (Table 3), x q l s³e ƒ Û20 % ü w w. t t ³ x w sƒ w Fig. 4. Mean plasma concentration-time curves of penciclovir in 24 human volunteers following single oral administration of reference preparation( ) and test preparation( ) at the dose of famciclovir 250 mg (mean S.D.). Analytical Science & Technology
7 p e w x r j HPLC w w x 329 Table 3. Bioequivalence parameters of penciclovir in 24 human volunteers after oral administration of reference tablet and test tablet at the famciclovir dose of 250 mg Parameter Reference (mean S.D.) Test (mean S.D.) 90% confidence interval AUC t (µg hr/ml) ~ C max (µg/ml) ~ T max (hr) w x - š l w x - š w (AUC t ), š x (C max ) y w, š x (T max ) š w. w vx 24 l K- BE Test 2002(ver ) v m w, T max w x sƒw de yw α( ) = 0.05 w. w sƒ w AUC t C max w K-BE Test v m, x ƒ y w, yw AUC t s³e 90 % log ~log log 0.8~log 1.25 ü w q» w, y w C max s³e 90 % log ~log q» g (Table 3). sƒw AUC t C max w w m y w. 0.1~5 µg/ml yw. ü 1.36~ 8.55 %, 0.93~5.62 %, y 92.8~100.0 %, w 0.1 µg/ml w w y, š y w. q j w w x w, w 24 x w m w, x j 250 mg q 250 mg w w x q» AUC t C max w q w w ( ) w w w t yw w,. š x y ƒ ƒwš p e w w x r j w w w. r j yw p w, ƒw š w ƒ jš, w,» w» Õ ñ x w š triethylamine ƒw» s g. w p e û w, w»», y gƒ w. w r j (validation) w, t x l w 1. M. R. Boyd, T. H. Bacon, D. Sutton and M. Cole, Antimicrob. Agents Chemother., 31, (1987). 2. M. R. Boyd, T. H. Bacon and D. Sutton, Antimicrob. Agents Chemother., 32, (1988). 3. T. H. Bacon and M. R. Boyd, Antimicrob. Agents Chemother., 39, (1995). 4. R. A. V. Hodge, D. Sutton, M. R. Boyd and M. Cole, Antiviral Res., 9, 146 (1988). 5. R. A. V. Hodge, D. Sutton, M. R. Boyd, M. R. Harnden and R. L. Jarvest, Antimicrob. Agents Chemother., 33(10), (1989). 6. K. S. Gill and M. J. Wood, Clin. Pharmacokinet., 31(1), 1-8(1996). 7. C. W. Filer, G. D. Allen, T. A. Brown, S. E. Fowles, F. Vol. 20, No. 4, 2007
8 330 ½ Á Á wá Á kyá J. Hollis, E. E. Mort, W. T. Prince and J. V. Ramji, Xenobiotica, 24(4), (1994). 8. C. W. Filer, J. V. Ramji, G. D. Allen, T. A. Brown, S. E. Fowles, F. J. Hollis and E. E. Mort, Xenobiotica, 25(5), (1995). 9. M. A. Pue, S. K. Pratt, A. J. Fairless, S. E. Fowles, J. Laroche, P. Georgiou and W. T. Prince, J. Antimicrob. Chemother., 33(1), (1994). 10. S. C. Boike, M. A. Pue, M. I. Freed, P. R. Audet, A. Fairless, B. E. Ilson, N. Zariffa and D. K. Jorkasky, Clin. Pharmacol. Ther., 55(4), (1994). 11. A. Loregian, R. Gatti, G. Palu and E. F. De Palo, J. Chromatogr. B, 764, (2001). 12. J. R. McMeekin, S. E. Fowles, C. F. Winton and D. M. Pierce, Anal. Proc., 29, (1992). 13. S. E. Fowles and D. M. Pierce, Analyst, 114(11), (1989). 14. H. A. Kang, H. Y. Cho, I. J. Oh, M. H. Lee and Y. B. Lee, J. Kor. Pharm. Sci., 35(4), (2005). 15. F. Schenkel, S. Rudaz, Y. Daali, M. K. Oestreicher, J. L. Veuthey and P. Dayer, J. Chromatogr. B, 826, 1-7(2005). 16. L. C. Hsu, D. J. C. Constable, D. R. Orvos and R. E. Hannah, J. Chromatogr. B, 669, (1995). 17. K. K. Phe and K. H. Yuen, J. Chromatogr. B, 693, (1997). 18. H. W. Lee, J. H. Seo and K. T. Lee, J. Chromatogr. B, 852, (2007). 19. P. D. Tzanavaras and D. G. Themelis, J. Pharm. Biomed. Anal., 43, (2007). 20. H. Kazoka, J. Biochem. Biophys. Methods, 70, (2007). 21. M. J. Ruiz-Angel, S. Carda-Broch and A. Berthod, J. Chromatogr. A, 1119, (2006). 22. G. Bahrami, S. Mirzaeei and A. Kiani, J. Chromatogr. B, 816, (2005). Analytical Science & Technology
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