Identification of finasteride metabolites in human bile and urine by high-performance liquid chromatography/tandem mass spectrometry

Drug Metabolism and Disposition

Volumn 37, Issue 10, 2009, Pages 2008-2017

  Lundahl, Anna ^a   Lennernäs, Hans ^a   Knutson, Lars ^b   Bondesson, Ulf ^a,c   Hedeland, Mikael ^a,c  

^a UPPSALA UNIVERSITY   (Sweden)

^b UPPSALA UNIVERSITY HOSPITAL   (Sweden)

^c NATIONAL VETERINARY INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

FINASTERIDE; FINASTERIDE OMEGA OIC ACID; GLUCURONOSYLTRANSFERASE 1A3; GLUCURONOSYLTRANSFERASE 1A4; HYPERICUM PERFORATUM EXTRACT; OMEGA HYDROXY FINASTERIDE; UNCLASSIFIED DRUG;

ADULT; ARTICLE; BILE; CLINICAL TRIAL; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; HYPERICUM PERFORATUM; IN VITRO STUDY; IN VIVO STUDY; INCUBATION TIME; INTESTINE; ION TRAP MASS SPECTROMETRY; JEJUNUM; LIVER MICROSOME; MALE; PHASE 1 CLINICAL TRIAL; PHASE 2 CLINICAL TRIAL; PRIORITY JOURNAL; QUADRUPOLE MASS SPECTROMETRY; TANDEM MASS SPECTROMETRY; URINALYSIS; URINE; VATER PAPILLA;

BILE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FINASTERIDE; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; MALE; MICROSOMES, LIVER; TANDEM MASS SPECTROMETRY; TUMOR CELLS, CULTURED;

EID: 70349277542     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.027870     Document Type: Article

References (37)

1. Benet LZ, Spahn-Langguth H, Iwakawa S, Volland C, Mizuma T, Mayer S, Mutschler E, and Lin ET (1993) Predictability of the covalent binding of acidic drugs in man. Life Sci 53:PL141-PL46. (Pubitemid 23216903)
2. Bergman E, Forsell P, Tevell A, Persson EM, Hedeland M, Bondesson U, Knutson L, and Lennernäs H (2006) Biliary secretion of rosuvastatin and bile acids in humans during the absorption phase. Eur J Pharm Sci 29:205-214. (Pubitemid 44602407)
3. Bønløkke L, Hovgaard L, Kristensen HG, Knutson L, Lindahl A, and Lennernäs H (1999) A comparison between direct determination of in vivo dissolution and the deconvolution technique in humans. Eur J Pharm Sci 8:19-27.
4. Carlin JR, Christofalo B, Arison C, Berman J, Brooks G, Rasmusson A, Rosegay E, Stoner E, and Vandenheuvel W (1987) Metabolism and disposition of MK-906 in laboratory animals and man (Abstract). Pharmacologist 29:149.
5. Carlin JR, Christofalo P, Arison BH, Ellsworth RE, Rosegay A, Miller RR, Chiu SH, and VandenHeuvel WJ (1997) Disposition and metabolism of finasteride in dogs. Drug Metab Dispos 25:100-109.
6. 14C]finasteride after oral administration in humans. Drug Metab Dispos 20:148-155.
7. Constanzer ML, Chavez CM, and Matuszewski BK (1994) Picogram determination of finasteride in human plasma and semen by high-performance liquid chromatography with atmospheric-pressure chemical-ionization tandem mass spectrometry. J Chromatogr B Biomed Appl 658:281-287. (Pubitemid 24268459)
8. Drake L, Hordinsky M, Fiedler V, Swinehart J, Unger WP, Cotterill PC, Thiboutot DM, Lowe N, Jacobson C, Whiting D, et al. (1999) The effects of finasteride on scalp skin and serum androgen levels in men with androgenetic alopecia. J Am Acad Dermatol 41:550-554. (Pubitemid 29480402)
9. Faller B, Farley D, and Nick H (1993) Finasteride: a slow-binding 5 α-reductase inhibitor. Biochemistry 32:5705-5710.
10. Fisher MB, Campanale K, Ackermann BL, VandenBranden M, and Wrighton SA (2000) In vitro glucuronidation using human liver microsomes and the pore-forming peptide alamethicin. Drug Metab Dispos 28:560-566. (Pubitemid 30238515)
11. Ghibellini G, Leslie EM, and Brouwer KL (2006a) Methods to evaluate biliary excretion of drugs in humans: an updated review. Mol Pharm 3:198-211. (Pubitemid 44021428)
12. Ghibellini G, Vasist LS, Hill TE, Heizer WD, Kowalsky RJ, and Brouwer KL (2006b) Determination of the biliary excretion of piperacillin in humans using a novel method. Br J Clin Pharmacol 62:304-308. (Pubitemid 44215530)
13. Gormley GJ, Stoner E, Bruskewitz RC, Imperato-McGinley J, Walsh PC, McConnell JD, Andriole GL, Geller J, Bracken BR, and Tenover JS (1992) The effect of finasteride in men with benign prostatic hyperplasia. The Finasteride Study Group. N Engl J Med 327:1185-1191.
14. Huskey SW, Dean DC, Miller RR, Rasmusson GH, and Chiu SH (1995) Identification of human cytochrome P450 isozymes responsible for the in vitro oxidative metabolism of finasteride. Drug Metab Dispos 23:1126-1135.
15. Ishii Y, Mukoyama H, Ishii M, Ohtawa M, and Carlin JR (1992) Sex difference in the metabolism of finasteride in the rats (abstract). ISSX Proceed 2:109.
16. Ishii Y, Mukoyama H, and Ohtawa M (1994) In vitro biotransformation of finasteride in rat hepatic microsomes: isolation and characterization of metabolites. Drug Metab Dispos 22:79-84. (Pubitemid 24045384)
17. Kang P, Dalvie D, Smith E, Zhou S, and Deese A (2007) Identification of a novel glutathione conjugate of flutamide in incubations with human liver microsomes. Drug Metab Dispos 35:1081-1088. (Pubitemid 46956427)
18. Knutson L, Odlind B, and Hällgren R (1989) A new technique for segmental jejunal perfusion in man. Am J Gastroenterol 84:1278-1284. (Pubitemid 19264720)
19. Kramer BS, Hagerty KL, Justman S, Somerfield MR, Albertsen PC, Blot WJ, Ballentine Carter H, Costantino JP, Epstein JI, Godley PA, et al. (2009) Use of 5-α-reductase inhibitors for prostate cancer chemoprevention: American Society of Clinical Oncology/American Urological Association 2008 Clinical Practice Guideline. J Clin Oncol 27:1502-1516.
20. Lennernäs H, Ahrenstedt O, Hällgren R, Knutson L, Ryde M, and Paalzow LK (1992) Regional jejunal perfusion, a new in vivo approach to study oral drug absorption in man. Pharm Res 9:1243-1251.
21. Loftsson T and Hreinsdóttir D (2006) Determination of aqueous solubility by heating and equilibration: a technical note. AAPS PharmSciTech 7:E4. (Pubitemid 43116031)
22. Lowe FC, McConnell JD, Hudson PB, Romas NA, Boake R, Lieber M, Elhilali M, Geller J, Imperto-McGinely J, Andriole GL, et al. (2003) Long-term 6-year experience with finasteride in patients with benign prostatic hyperplasia. Urology 61:791-796. (Pubitemid 36384975)
23. Lundahl A, Hedeland M, Bondesson U, Knutson L, and Lennernäs H (2009) The effect of St. John's wort on the pharmacokinetics, metabolism and biliary excretion of finasteride and its metabolites in healthy men. Eur J Pharm Sci 36:433-443.
24. McConnell JD, Wilson JD, George FW, Geller J, Pappas F, and Stoner E (1992) Finasteride, an inhibitor of 5 α-reductase, suppresses prostatic dihydrotestosterone in men with benign prostatic hyperplasia. J Clin Endocrinol Metab 74:505-508.
25. Ohtawa M, Morikawa H, and Shimazaki J (1991) Pharmacokinetics and biochemical efficacy after single and multiple oral administration of N-(2-methyl-2-propyl)-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide, a new type of specific competitive inhibitor of testosterone 5α-reductase, in volunteers. Eur J Drug Metab Pharmacokinet 16:15-21.
26. Persson EM, Nilsson RG, Hansson GI, Löfgren LJ, Libäck F, Knutson L, Abrahamsson B, and Lennernäs H (2006) A clinical single-pass perfusion investigation of the dynamic in vivo secretory response to a dietary meal in human proximal small intestine. Pharm Res 23:742-751.
27. Rittmaster RS, Stoner E, Thompson DL, Nance D, and Lasseter KC (1989) Effect of MK-906, a specific 5 α-reductase inhibitor, on serum androgens and androgen conjugates in normal men. J Androl 10:259-262. (Pubitemid 19206758)
28. Shibasaki H, Tanabe C, Furuta T, and Kasuya Y (2001) Hydrolysis of conjugated steroids by the combined use of β-glucuronidase preparations from Helix pomatia and ampullaria: determination of urinary cortisol and its metabolites. Steroids 66:795-801. (Pubitemid 32884305)
29. Shipkova M, Armstrong VW, Oellerich M, and Wieland E (2003) Acyl glucuronide drug metabolites: toxicological and analytical implications. Ther Drug Monit 25:1-16. (Pubitemid 36139819)
30. Steiner JF (1996) Clinical pharmacokinetics and pharmacodynamics of finasteride. Clin Pharmacokinet 30:16-27.
31. Sudduth SL and Koronkowski MJ (1993) Finasteride: the first 5 α-reductase inhibitor. Pharmacotherapy 13:309-329.
32. Teichert J, Sohr R, Hennig L, Baumann F, Schoppmeyer K, Patzak U, and Preiss R (2009) Identification and quantitation of the N-acetyl-L-cysteine S-conjugates of bendamustine and its sulfoxides in human bile after administration of bendamustine hydrochloride. Drug Metab Dispos 37:292-301.
33. Thompson IM, Goodman PJ, Tangen CM, Lucia MS, Miller GJ, Ford LG, Lieber MM, Cespedes RD, Atkins JN, Lippman SM, et al. (2003) The influence of finasteride on the development of prostate cancer. N Engl J Med 349:215-224. (Pubitemid 36859473)
34. Tian G (1996) In vivo time-dependent inhibition of human steroid 5 α-reductase by finasteride. J Pharm Sci 85:106-111.
35. van der Woude H, Boersma MG, Vervoort J, and Rietjens IM (2004) Identification of 14 quercetin phase II mono- and mixed conjugates and their formation by rat and human phase II in vitro model systems. Chem Res Toxicol 17:1520-1530. (Pubitemid 39532321)
36. Vaughan D, Imperato-McGinley J, McConnell J, Matsumoto AM, Bracken B, Roy J, Sullivan M, Pappas F, Cook T, Daurio C, et al. (2002) Long-term (7 to 8-year) experience with finasteride in men with benign prostatic hyperplasia. Urology 60:1040-1044. (Pubitemid 35447563)
37. Venkataramani ES, Carlin JR, Dolling U, Christofalo P, Magliette RJ, Arison BH, and Stearns RA (1994) Biotransformation of finasteride (MK-0906) by Selenastrum capricornutum (green algae). Ann N Y Acad Sci 745:51-60. (Pubitemid 26005844)