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Xenobiotica
the fate of foreign compounds in biological systems
Volume 41, 2011 - Issue 3
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General Xenobiochemistry

Microbial production of phase I and phase II metabolites of propranolol

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Pages 175-186 | Received 15 Sep 2010, Accepted 24 Oct 2010, Published online: 26 Nov 2010

References

  • Barrett AM, Cullum VA. (1968). The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias. Br J Pharmacol 34:43–55.
  • Baughman TM, Talarico CL, Soglia JR. (2009). Evaluation of the metabolism of propranolol by linear ion trap technology in mouse, rat, dog, monkey, and human cryopreserved hepatocytes. Rapid Commun Mass Spectrom 23:2146–2150.
  • Beaudry F, Yves Le Blanc JC, Coutu M, Ramier I, Moreau JP, Brown NK. (1999). Metabolite profiling study of propranolol in rat using LC/MS/MS analysis. Biomed Chromatogr 13:363–369.
  • Bichara N, Ching MS, Blake CL, Ghabrial H, Smallwood RA. (1996). Propranolol hydroxylation and N-desisopropylation by cytochrome P4502D6: studies using the yeast-expressed enzyme and NADPH/O2 and cumene hydroperoxide-supported reactions. Drug Metab Dispos 24:112–118.
  • Borges KB, Pupo MT, Bonato PS. (2009). Enantioselective analysis of propranolol and 4-hydroxypropranolol by CE with application to biotransformation studies employing endophytic fungi. Electrophoresis 30:3910–3917.
  • Di Nardo G, Fantuzzi A, Sideri A, Panicco P, Sassone C, Giunta C, Gilardi G. (2007). Wild-type CYP102A1 as a biocatalyst: turnover of drugs usually metabolised by human liver enzymes. J Biol Inorg Chem 12:313–323.
  • Foster BC, Buttar HS, Qureshi SA, McGilveray IJ. (1989). Propranolol metabolism by Cunninghamella bainieri. Xenobiotica 19:539–546.
  • Foster BC, Litster DL, Wilson DL, Ormsby E, Dawson BA. (1992). In vitro assessment of cytotoxicity and biotransformation of propranolol in Cunninghamella echinulata. Xenobiotica 22:1221–1228.
  • Hanioka N, Hayashi K, Shimizudani T, Nagaoka K, Koeda A, Naito S, Narimatsu S. (2008). Stereoselective glucuronidation of propranolol in human and cynomolgus monkey liver microsomes: role of human hepatic UDP-glucuronosyltransferase isoforms, UGT1A9, UGT2B4 and UGT2B7. Pharmacology 82:293–303.
  • Huang H, Chen X, Cui H, Zhong D. (2001). Synthesis of 5-hydroxypropranolol by microbial transformation. Yaowu Shengwu Jishu 8:268–271.
  • Kinne M, Poraj-Kobielska M, Aranda E, Ullrich R, Hammel KE, Scheibner K, Hofrichter M. (2009). Regioselective preparation of 5-hydroxypropranolol and 4′-hydroxydiclofenac with a fungal peroxygenase. Bioorg Med Chem Lett 19:3085–3087.
  • Lampinen Salomonsson M, Bondesson U, Hedeland M. (2009). In vitro formation of phase I and II metabolites of propranolol and determination of their structures using chemical derivatization and liquid chromatography–tandem mass spectrometry. J Mass Spectrom 44:742–754.
  • Luan LJ, Shao Q, Zeng S. (2005). Stereoselectivity and interaction between the glucuronidation of S-(−)- and R-(+)-propranolol in rat hepatic microsomes pretreated with different inducers. Pharmazie 60:221–224.
  • Masubuchi Y, Hosokawa S, Horie T, Suzuki T, Ohmori S, Kitada M, Narimatsu S. (1994). Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos 22:909–915.
  • Narimatsu S, Arai T, Masubuchi Y, Horie T, Hosokawa M, Ueno K, Kataoka H, Yamamoto S, Ishikawa T, Cho AK. (2001). Inactivation of rat cytochrome P450 2D enzyme by a further metabolite of 4-hydroxypropranolol, the major and active metabolite of propranolol. Biol Pharm Bull 24:988–994.
  • Nelson WL, Bartels MJ. (1984). Stereoselectivity in the aromatic hydroxylation of propranolol in the rat: use of deuterium labeling and pseudoracemic mixtures. Drug Metab Dispos 12:382–384.
  • Oatis JE Jr, Baker JP, McCarthy JR, Knapp DR. (1983). Synthesis and chromatographic separation of the glucuronides of (R)- and (S)-propranolol. J Med Chem 26:1687–1691.
  • Oatis JE Jr, Russell MP, Knapp DR, Walle T. (1981). Ring-hydroxylated propranolol: synthesis and beta-receptor antagonist and vasodilating activities of the seven isomers. J Med Chem 24:309–314.
  • Otey CR, Bandara G, Lalonde J, Takahashi K, Arnold FH. (2006). Preparation of human metabolites of propranolol using laboratory-evolved bacterial cytochromes P450. Biotechnol Bioeng 93:494–499.
  • Otton SV, Gillam EM, Lennard MS, Tucker GT, Woods HF. (1990). Propranolol oxidation by human liver microsomes—the use of cumene hydroperoxide to probe isoenzyme specificity and regio- and stereoselectivity. Br J Clin Pharmacol 30:751–760.
  • Pham-Huy C, Sahui-Gnassi A, Saada V, Gramond JP, Galons H, Ellouk-Achard S, Levresse V, Fompeydie D, Claude JR. (1994). Microassay of propranolol enantiomers and conjugates in human plasma and urine by high-performance liquid chromatography after chiral derivatization for pharmacokinetic study. J Pharm Biomed Anal 12:1189–1198.
  • Silber B, Holford NH, Riegelman S. (1982). Stereoselective disposition and glucuronidation of propranolol in humans. J Pharm Sci 71:699–704.
  • Sten T, Qvisen S, Uutela P, Luukkanen L, Kostiainen R, Finel M. (2006). Prominent but reverse stereoselectivity in propranolol glucuronidation by human UDP-glucuronosyltransferases 1A9 and 1A10. Drug Metab Dispos 34:1488–1494.
  • Thompson JA, Hull JE, Norris KJ. (1981). Glucuronidation of propranolol and 4′-hydroxypropranolol. Substrate specificity and stereoselectivity of rat liver microsomal glucuronyltransferases. Drug Metab Dispos 9:466–471.
  • Tindell GL, Walle T, Gaffney TE. (1972). Rat liver microsomal metabolism of propranolol: identification of seven metabolites by gas chromatography–mass spectrometry. Life Sci II 11:1029–1036.
  • von Bahr C, Hermansson J, Lind M. (1982). Oxidation of (R)- and (S)-propranolol in human and dog liver microsomes. Species differences in stereoselectivity. J Pharmacol Exp Ther 222:458–462.
  • Walle T, Oatis JE Jr, Walle UK, Knapp DR. (1982). New ring-hydroxylated metabolites of propranolol: species differences and stereospecific 7-hydroxylation. Drug Metab Dispos 10:122–127.
  • Walle T, Walle UK, Olanoff LS. (1985). Quantitative account of propranolol metabolism in urine of normal man. Drug Metab Dispos 13:204–209.
  • Yoshimoto K, Echizen H, Chiba K, Tani M, Ishizaki T. (1995). Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers—N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol 39:421–431.
  • Yu L, Qian M, Liu Y, Yao T, Zeng S. (2010). Stereoselective metabolism of propranolol glucuronidation by human UDP-glucuronosyltransferases 2B7 and 1A9. Chirality 22:456–461.
  • Yun CH, Kim KH, Kim DH, Jung HC, Pan JG. (2007). The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol 25:289–298.

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