Aromatase is the major enzyme metabolizing buprenorphine in human placenta

Journal of Pharmacology and Experimental Therapeutics

Volumn 306, Issue 3, 2003, Pages 1099-1105

  Deshmukh, Sujal V ^a   Nanovskaya, Tatiana N ^a   Ahmed, Mahmoud S ^a  

^a University of Texas Medical Branch School of Medicine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLUTETHIMIDE; AROMATASE; BUPRENORPHINE; CYTOCHROME P450; FORMESTANE; MONOCLONAL ANTIBODY; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; DEALKYLATION; DRUG DEPENDENCE; DRUG EFFECT; ENZYME ACTIVITY; ENZYME METABOLISM; FETUS CIRCULATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; MASS SPECTROMETRY; MICROSOME MEMBRANE; PLACENTA; PRIORITY JOURNAL;

ALKYLATION; ANTIBODIES; AROMATASE; AROMATASE INHIBITORS; BUPRENORPHINE; CYTOCHROME P-450 ENZYME SYSTEM; DNA, COMPLEMENTARY; ENZYME INHIBITORS; FEMALE; HUMANS; KINETICS; MIXED FUNCTION OXYGENASES; NARCOTICS; PLACENTA; PREGNANCY; SUBCELLULAR FRACTIONS;

EID: 0042934006     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: 10.1124/jpet.103.053199     Document Type: Article

References (37)

1. Ayub M and Levell MJ (1988) Structure-activity relationships of the inhibition of human placental aromatase by imidazole drugs including ketoconazole. J Steroid Biochem 31:65-72.
2. Baldwin SJ, Bloomer JC, Smith GJ, Ayrton AD, Clarke SE, and Chenery RJ (1995) Ketoconazole and sulphaphenazole as the respective selective inhibitors of P4503A and 2C9. Xenobiotica 25:261-270.
3. Blanck A, Rane A, Toftgard R, and Gustafsson JA (1983) Biotransformation of benzo[a]pyrene and 7-ethoxyresorufin and heme-staining proteins in microsomes from human fetal liver and placenta. Biochem Pharmacol 32:1547-1552.
4. Bourrie M, Meunier V, Berger Y, and Fabre G (1996) Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J Pharmacol Exp Ther 277:321-332.
5. Buters JT, Schiller CD, and Chou RC (1993) A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man. Direct fluorescence monitoring of the deethylation of 7-ethoxy-4-trifluoromethylcoumarin. Biochem Pharmacol 46:1577-1584.
6. Cone EJ, Gorodetzky CW, Yousefnejad D, Buchwald WF, and Johnson RE (1984) The metabolism and excretion of buprenorphine in humans. Drug Metab Dispos 12: 577-581.
7. Contractor SF (1983) Metabolic and enzymatic activity of human trophoblasts, in Biology of Trophoblasts (Loke YW and Whyte A eds) pp 235-281, Elsevier, Oxford.
8. DeLuca JG, Dysart GR, Rasnick D, and Bradley MO (1988) A direct, highly sensitive assay for cytochrome P-450 catalyzed O-deethylation using a novel coumarine analog. Biochem Pharmacol 37:1731-1739.
9. Eder H, Rupp I, Peternell A, and Fischer G (2001) Buprenorphine in pregnancy]. Psychiatr Prax 28:267-269.
10. Fabre G, Julian B, Saint-Aubert B, Joyeux H, and Berger Y (1993) Evidence for CYP3A-mediated N-deethylation of amiodarone in human liver microsomal fractions. Drug Metab Dispos 21:978-985.
11. Finkelstein M, Neiman G, and Mizrahi Y (1985) Human placenta mitochondrial aromatase - Fact or artifact. Steroids 45:277-278.
12. Fischer G, Johnson RE, Eder H, Jagsch R, Peternell A, Weninger M, Langer M, and Aschauer HN (2000) Treatment of opioid-dependent pregnant women with buprenorphine. Addiction 95:239-244.
13. Hakkola J, Pasanen M, Hukkanen J, Pelkonen O, Maenpaa J, Edwards RJ, Boobis AR, and Raunio H (1996a) Expression of xenobiotic-metabolizing cytochrome P450 forms in human full-term placenta. Biochem Pharmacol 51:403-411.
14. Hakkola J, Raunio H, Purkunen R, Pelkonen O, Saarikoski S, Cresteil T, and Pasanen M (1996b) Detection of cytochrome P450 gene expression in human placenta in first trimester of pregnancy. Biochem Pharmacol 52:379-383.
15. Iribarne C, Picart D, Dreano Y, Bail JP, and Berthou F (1997) Involvement of cytochrome P450 3A4 in N-dealkylation of buprenorphine in human liver microsomes. Life Sci 60:1953-1964.
16. Jarvis MA and Schnoll SH (1994) Methadone treatment during pregnancy. J Psychoact Drugs 26:155-161.
17. Juchau MR (1980) Drug biotransformation in the placenta. Pharmacol Ther 8:501-524.
18. Kitawaki J, Yoshida N, and Osawa Y (1989) An enzyme-linked immunosorbent assay for quantitation of aromatase cytochrome P-450. Endocrinology 124:1417-1423.
19. Kobayashi K, Yamamoto T, Chiba K, Tani M, Shimada N, Ishizaki T, and Kuroiwa Y (1998) Human buprenorphine N-dealkylation is catalyzed by cytochrome P450 3A4. Drug Metab Dispos 26:818-822.
20. Lejeune C, Aubisson S, Simmant-Durand L, Cneude F, Piquet M, and Gourarier L (2001) [Withdrawal syndromes of newborns of pregnant drug abusers maintained under methadone or high-dose buprenorphine: 246 cases.] Ann Med Interne (Paris) 152:21-27.
21. Marquet P, Chevrel J, Lavignasse P, Merle L, and Lachatre G (1997) Buprenorphine withdrawal syndrome in a newborn. Clin Pharmacol Ther 62:569-571.
22. McNamara J, Stocker P, Miller VP, Patten CJ, Stresser DM, and Crespi C (1999) CYP 19 (Aromatase): Characterization of the recombinant enzyme and its role in the biotransformation of xenobiotics. Gentest Corporation website: www.gentest. com/pdf/post-016. pdf.
23. Meigs RA (1987) The constitutive 7-ethoxycoumarin-O-deethylase activity of human placental microsomes: relation to aromatase. Biochem Biophys Res Commun 145: 1012-1018.
24. Moody DE, Slawson MH, Strain EC, Laycock JD, Spanbauer AC, and Foltz RL (2002) A liquid chromatographic-electrospray ionization-tandem mass spectrometric method for determination of buprenorphine, its metabolite, norbuprenorphine and a coformulant, naloxone, that is suitable for in vivo and in vitro metabolism studies. Anal Biochem 306:31-39.
25. Nandakumaran M, Gardey CL, Challier JC, Richard MO, Panigel M, and Olive G (1983) Transfer of salbutamol in the human placenta in vitro. Dev Pharmacol Ther 3:88-98.
26. Nanovskaya T, Deshmukh S, Brooks M, and Ahmed MS (2002) Transplacental transfer and metabolism of buprenorphine. J Pharmacol Exp Ther 300:26-33.
27. Newton DJ, Wang RW, and Lu AY (1995) Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab Dispos 23:154-158.
28. Osawa Y, Higashiyama T, Toma Y, and Yarborough C (1997) Diverse function of aromatase and the N-terminal sequence deleted form. J Steroid Biochem Mol Biol 61:117-126.
29. Pasanen M, Haaparanta T, Sundin M, Sivonen P, Vakakangas K, Raunio H, Hines R, Gustafsson JA, and Pelkonen O (1990) Immunochemical and molecular biological studies on human placental cigarette smoke-inducible cytochrome P-450-dependent monooxygenase activities. Toxicology 62:175-187.
30. Pasanen M, Raunio H, and Pelkonen O (1985) Freezing affects the activity and subcellular distribution profile of human placental xenobiotic- and steroid-metabolizing enzymes. Placenta 6:527-535.
31. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, and Raunio H (1998) Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica 28:1203-1253.
32. Pienimaki P, Lampela E, Hakkola J, Arvela P, Raunio H, and Vahakangas K (1997) Pharmacokinetics of oxcarbazepine and carbamazepine in human placenta. Epilepsia 38:309-316.
33. Roe DA, Little BB, Bawdon RE, and Gilstrap LC 3rd (1990) Metabolism of cocaine by human placentas: implications for fetal exposure. Am J Obstet Gynecol 163:715-718.
34. Stresser DM, Turner SD, McNamara J, Stocker P, Miller VP, Crepsi CL, and Patten CJ (2000) A high-throughput screen to identify inhibitors of aromatase (CYP19). Anal Biochem 284:427-430.
35. Taniguchi H, Feldmann HR, Kaufmann M, and Pyerin W (1989) Fast liquid chromatographic assay of androgen aromatase activity. Anal Biochem 181:167-171.
36. Thompson EA Jr and Siiteri PK (1974) The involvement of human placental microsomal cytochrome P-450 in aromatization. J Biol Chem 249:5373-5378.
37. Toma Y, Higashiyama T, Yarborough C, and Osawa Y (1996) Diverse functions of aromatase: O-deethylation of 7-ethoxycoumarin. Endocrinology 137:3791-3796.