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1 Printed in the Republic of Korea "/"-:5*$"- 4$*&/$& 5&$)/0-0(: Vol. 25, No. 1, 76-82, $.4.4wxEVUBTUFSJEF ûxáû Á ÁÁ Áy Á½kÁ» Á k ÁxÁŸyÁ³, ttsƒ twsƒ, 1 sƒ Analysis of dutasteride in human serum by LC-MS/MS Hye-Seon Nam, Kyong-Hee Nam, Su Hee Jung, Jang Woo Lee, Jin Yeong Kang, Soon Keun Hong,G Tae Sung Kim, Ki Kyung Jung, Tae Seok Kang 1, Hae-Jung Yoon, Kwang Ho Lee and Gyu-Seek Rhee Food Safety Evaluation Department, 1 Toxicology Evaluation and Research Department, National Institute of Food and Drug Safety Evaluation, Korea Food and Drug Administration Osong Health Technology Administration Complex, 187 Osongsaengmyeong 2(i)-ro, Gangoe-myeon, Cheongwon-gun, Chungcheongbuk-do , Korea (Received October 14, 2011; Revised November 15, 2011; Accepted December 16, 2011) : x kl y w LC-ESI-MS/MS w wš, k wš ww. üt jk ƒw x methyl tert-butyl ether (MTBE) w (liquid-liquid extraction, LLE) w. LC-MS/MS MRM (multiple reaction monitoring) yw kl jk mass transition ƒƒ m/z , m/z , ƒƒ 6.45, ~30.0 ng/ml R 2 = ù kü, w z ƒƒ 0.5 ng/ml 66~72%. ü w 3.5~5.5%, y 85.7~89.9%, 3 ww 4.2~5.8%, y 90.8~95.8%. Abstract: The determination and confirmation of dutasteride in human serum was performed by a liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI/MS/MS). Beclomethasone as an internal standard (I.S.) was added to the serum and the mixed sample was pretreated by liquid-liquid extraction (LLE) with methyl tert-butyl ether (MTBE). The mass transitions of dutasteride and I.S. monitored in multiple reaction monitoring (MRM) were m/z and m/z , respectively, and the retention times were 6.45 and 5.46 min, respectively. The calibration curve was linear in the concentration range of 0.5~30.0 ng/ml (R 2 = ) and the limit of quantitation (LOQ) was found to be 0.5 ng/ml. The recovery of dutasteride was shown to be 66~72%. The intra-day assay precision and accuracy were in the range 3.5~5.5% and 85.7~89.9%, respectively, and the interday assay precision and accuracy were in the range 4.2~5.8% and 90.8~95.8%, respectively. Key words: Dutasteride, LC-MS/MS, human serum Corresponding author Phone : +82-(0) Fax : +82-(0) gsrhee@kfda.go.kr 76
2 LC-MS/MS w x dutasteride 77 kl(dutasteride, Fig. 1a) 4-l (azasteroid) wyw 5-α-reductase z y g ûy lml(testosterone) wlml(dihydrotestosterone, DHT) w.kl p (Avodart) 2001 t (FDA) (benign prostatic hyperplasia, BPH) e, z w û w y w(lower urinary tract symptom, LUTS) ûx k(male pattern baldness, MPB) ew zƒ šš. 1-9 w» ùkü FDA e(proscar, 1992) ûx k e (Propecia, 1997) vùl (finasteride)ƒ 5-α-reductase z Type 2 isoenzyme k j w, kl Type 1 Type 2 isoenzyme j. w vùl kl z w vùl klƒ 5-α-reductase z z w šwš, p k lƒ vùl Type 2 isoenzyme y 3 jš Type 1 isoenzyme , kš šwš. ù kl x¾ y. w ûy DHT y w w» kl û k»»x ƒ w, ù ƒ kl kl e ƒ w. w û 5-α-reductase Type 2 w ù kú, û»»,, x ùkú , kl x mw ù ƒ w» k l n š 6 w û xx w x wš kl š k»x ƒ ƒw w x w xx š, x kl w. ù kl 17 Ramakrishna et al. (2004) w x(plasma) LC-MS/MS w z k (Tamsulosin) y t(alfuzosin) x kl w, ü y LC-ESI/MS/MS w x kl dw wš, k w š ww. kl(99%, Fig. 1a) t jk(99%, Fig. 1b) üt ƒƒ AKSci(CA, USA) Sigma-Aldrich(St. Louis, MO, USA)t wš, tx(human serum) PAA Laboratories(Cölbe, Germany)t w. LC-MS/MS w HPLC š wš, mp Merck(Darmstadt, Germany), k (formic acid) ƒƒ J.T. Baker(Phillipsburg, NJ, USA)t w. methyl tert-butyl ether (MTBE) ke(k 2 CO 3 ) ƒƒ Sigma-Aldrich(St. Louis, MO, USA), Wako (Junyaku, Japan)t w. x Fig. 1. Chemical structures of (a) dutasteride and (b) beclomethasone (I.S). Vol. 25, No. 1, 2012
3 78 ûxáû Á ÁÁ Áy Á½kÁ» Á káxáÿyá³»» e w LC-MS/MS Agilent 1200 Series HPLC (Agilent Technologies, Palo Alto, CA, USA) triple quadruple l»(api 4000, Applied Biosystems, USA) w. HPLC e Imtakt Corporation(Kyoto, Japan) Unison UK-C18 column (2 mm i.d 75 mm length, 3 µm particle size) w.» Beckman Coulter(Fullerton, CA, USA) Allegra 6R w š, vortex-mixer Scientific Industries(Bohemia, NY, USA) Vortex-Genie 2 w. Shaker IKA Labortechnik(Staufen, Germany) HS 250 basic wš,» Zymark(CA, USA) Turbovap LV evaporator w. Fig. 2. Schematic diagram of the sample preparation. x t kl tt k 1000 µg/ mlƒ t(stock solution) wš t 200, 100, 50, 20, 10, 2, 1 ng/ml ƒ k w t w. ütt jk k 1000 µg/mlƒ t w z k w 100, 50 ng/ml t w. -70 C þ w w o w z w. x 200 µl üt (jk) 20 µl ƒw z(vortexing, 30 sec), mp 400 µl e g.» ke ƒw z MTBE 5 ml š 20 wš, 3000 rpm 10 w w z N 2 evaporator (30 C) o w šw. š LC-MS/MS Table 1. Experimented conditions of LC-MS/MS LC conditions HPLC Agilent 1200 series Column Unison UK-C18 (2 75 mm, 3 µm) Column oven 35 o C Flow Rate 250 µl/min Injection 5 µl Mobile phase A: 0.1% formic acid in water, B: acetonitrile Gradient: B 10% (0 min) B 10% (1 min) B 97% (4 min) B 97% (6 min) B 10% (6.1 min) B 10% (11 min) MS/MS conditions MS/MS API 4000 Curtain gas (psi) 10 Ion source ESI Collision gas (psi) 5 Detection mode Positive Ion spray voltage (V) 4500 Source temperature ( o C) 300 Declustering potential (DP) (V) 90 Dwell time (ms) 150 Entrance potential (EP) (V) 10 Ion source gas(gas1) (psi) 25 Collision energy (CE) (V) 46 Ion source gas(gas2) (psi) 50 Collision cell exit potential (CXP) (V) 13 Analytical Science & Technology
4 100 µl z(vortexing, 30 sec), micro-filtering (0.45 µl, PTEE)w LC-MS/MS 5 µl w w(fig. 2).»» e Table 1»» LC-MS/MS w w. e Unison UK-C18 column (2 mm i.d 75 mm length, 3 µm particle size) wš, 0.1% sw mp»» (gradient elution) w 250 µl/min w. e 35 C w o w. w MS/MS»y (electrospray ionization, ESI) kwš (+) MRM (multiple reaction monitoring) w.» ƒ w 300 o C, ion spray voltage 4500 V.»k MS/MS ql declustering potential 90 V, entrance potential 10 V, collision energy 46 V, collision cell exit potential 13 V w w. LC-MS/MS w x dutasteride 79 Bioanalytical Method Validation ww yw w (LOQ) y (signal) (noise) 10» w. kl t (0.5, 1.0, 2.0, 5.0, 10.0, 20.0, 30.0 ng/ml) w w w 5z ww z w. kl QC»,, š ƒƒ 1.5, 12.0, 24.0 ng/ml w w w x 5 ww ü (precision), y(accuracy) wš, w 3 x ww, y w k w. š -$.4.4 rp x kl w LC-MS/ MS wš, Table 1 ùkü. kl üt jk Fig. 3. Electrospray product ion mass spectra of (a) dutasteride and (b) beclomethasone (I.S). y w (+) Q1 scan wš, m/z [M+H] + ww vj yw z, y(quantitative optimization) ww (precursor ion) (product ion) yw., kl m/z 529.6m/z 461.5, üt jk m/z 409.3m/z d(fig. 3). k Blank w ƒw x w z LC-ESI/MS/MS w jm Fig. 4 ùkü. Fig. 4(a) üt blank üt jk 5.46 klƒ š, 0.5 ng/ml dutasteride klƒ 6.45 yw v j ùkü(fig. 4(b)). Vol. 25, No. 1, 2012
5 남혜선 남경희 정수희 이장우 강진영 홍순근 김태성 정기경 강태석 윤혜정 이광호 이규식 80 Fig. 4. Chromatogram of (a) blank (drug free spiked with internal standard) human serum and (b) 0.5 ng/ml spiked dutasteride with the internal standard 직선성 검량선 작성을 위해 혈청 중 농도가 0.5~30.0 ng/ ml의 범위가 되도록 표준물질을 가한 후 전처리 과 정을 거쳐 검량선을 작성하였으며, 표준용액의 농도범 위에서 상관계수 (R ) 의 우수한 직선성을 확인 하였다(Fig. 5) 정확도, 정밀도. 5. Linearity of the standard calibration curve of dutasteride. Fig 0.5~30.0 ng/ml의 농도범위에서 실시한 검량선 시 료의 일내 정밀도는 변동계수(coefficient of variation, CV)가 2.4~8.4%로 생체시료분석법 밸리데이션 가이 던스인 15%를 만족하였으며, 정확도는 92.5~103.8% 로 생체시료분석법 가이던스인 80~120%를 만족하였 Analytical Science & Technology
6 LC-MS/MS w x dutasteride 81 Table 2. Precision and accuracy data of backed-calculated concentration of calibration samples for dutasteride in human serum Spiked Conc. (ng/ml) MeanÛSD n=5 *Precision **Accuracy Û Û Û Û Û Û Û * C.V.=STDEV of measured concentration/means of measured concentration ** Accuray = Measured concentration/spiked concentration Table 3. Precision and accuracy for the determination of dutasteride in human serum Spiked Conc. (ng/ml) Inter-day (n=5) Precision Accuracy Intra-day (n=3) Precision Accuracy (Table 2).» ƒ ( 1.5 ng/ml, 12.0 ng/ml, š 24.0 ng/ml) w w x 5 ww w ü y 85.7~89.9%, w 3 ww y 90.8~95.8% ƒ w(table 3). w ƒ ( 1.5 ng/ml, 12.0 ng/ml, š 24.0 ng/ ml) w ü, ƒ ƒ ƒ 3.5~5.5%, 4.2~5.8% ƒ 15% w(table 3). kl w x w» w y ƒ š yw. z w z w» w w z e» z kl üt vj w w ng/ml d w z 65.6% 72.4% ƒƒ ùkü Table 4. Recovery of dutasteride from human serum Spiked Conc. (ng/ml) Recovery (Table 4). Ramakrishna et al.(2004) 17 (40.7%) w z ùkü. x kl w LC-MS/MS w yw, w w. kl w z ƒƒ 0.5 ng/ml, 66~72% š, 0.5~30.0 ng/ml w (R 2 = ) ùkü. LC-MS/MS x ü kl y w k, y ƒš, x w xx kl w». šx 1. C. G. Roehrborn, P. Boyle, J. C. Nickel, K. Hoefner and G. Andriole, Urol., 60, (2002). 2. H. C. Evans and K. L. Goa, Drugs Aging., 20(12), (2003). 3. K. K. Gaines, Urol. Nurs., 23(3), (2003). 4. G. L. Andriole and R. Kirby, Eur. Urol., 44, (2003). 5. F. Debruyne, J. Barkin, P. van Erps, M. Reis, T. L. J. Tammela and C. Roehrborn, Eur. Urol., 46(4), (2004). 6. R. V. Clark, D. J. Hermann, G. R. Cunningham, T. H. Wilson, B. B. Morrill and S. Hobbs, J. Clin. Endocrinol Metab., 89(5), (2004). 7. E. A. Olsen, M. Hordinskym, D. Whiting, D. Stough, S. Hobbs, M. L. Ellis, T. Wilson and R. S. Rittmaster, J. AM ACAD DERMATOL., 55(6), (2006). 8. M. Marberger, C. G. Roehrborn, L. S. Marks, T. Wilson and R. S. Rittmaster, J. Clin. Endocrinol. Metab., Vol. 25, No. 1, 2012
7 82 ûxáû Á ÁÁ Áy Á½kÁ» Á káxáÿyá³ 91(4), (2006). 9. C. G. Roehrborn, P. Siami, J. Barkin, R. Damião, K. Major-Walker, B. Morrill and F. Montorsi, CombAT Study Group, J. Urol., 179(2), (2008). 10. J. C. Nickel, Urol., 6(9), S31-39 (2004). 11. N. Makridakis and J. K. V. Reichardt, J. Mol. Endocrinol., 34, (2005). 12. J. K. Amory, C. Wang, R. S. Swerdloff, B. D. Anawalt, A. M. Matsumoto, W. J. Bremner, S. E. Walker, L. J. Haberer and R. V. Clark, J. Clin. Endocrinol. Metab., 92(5), (2007). 13. C. L. Foley, S. R. Bott, I. S. Shergill and R. S. Kirby, Drugs. Today., 40(3), 213 (2004). 14. A. M. Traish, J. Hassani, A. T. Guay, M. Zitzmann and M. L. Hansen, J. Sexual. Medicine., 8(3), (2011). 15. Blood Guidances, Food and Drug Administration, USA, Blood Regulation Law, Ministry of Health and Welfare, Korea, N. V. S. Ramakrishna, K. N. Vishwottam, S. Puran, M. Koteshwara, S. Manoj and M. Santosh, J. Chromatogr B., 809(1), (2004). 18. S. Agarwal, K. V. Gowda, A. K. Sarkar, D. Ghosh, U. Bhaumik, T. K. Chattarai and T. K. Pal, Chromatographia., 67, (2008). 19. N. A. Gomes, A. Pudage, S. S. Joshi, V. V. Vaidya, S. A. Parekh and A. V. Tamhankar, Chromatographia., 69, 9-18 (2009). 20. Bioanalytical Method Validation, National Institute of Food and Drug Safety Evaluation, Korea, Guidance for Industry, Bioanalytical Method Validation, Food and Drug Administration, USA, Analytical Science & Technology
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