Identification of fungal metabolites of anticonvulsant drug carbamazepine

Applied Microbiology and Biotechnology

Volumn 79, Issue 4, 2008, Pages 663-669

  Kang, Su Il ^a   Kang, Seo Young ^a   Hur, Hor Gil ^a  

^a Gwangju Institute of Science and Technology (GIST)   (South Korea)

Author keywords

Carbamazepine; Cunninghamella elegans; Epoxidation; Mono oxygenation; Umbelopsis ramanniana

Indexed keywords

DISEASE CONTROL; METABOLISM; METABOLITES; RATS;

CARBAMAZEPINE; CUNNINGHAMELLA ELEGANS; MONO-OXYGENATION; UMBELOPSIS RAMANNIANA;

FUNGI;

2 HYDROXYCARBAMAZEPINE; 3 HYDROXYCARBAMAZEPINE; ANTICONVULSIVE AGENT; CARBAMAZEPINE; CARBAMAZEPINE 10,11 OXIDE; DRUG METABOLITE; OXYGEN;

DRUG; ENVIRONMENTAL FATE; FUNGUS; IDENTIFICATION METHOD; LIQUID CHROMATOGRAPHY; METABOLISM; METABOLITE; OXIDATION; OXYGEN;

ARTICLE; CUNNINGHAMELLA ELEGANS; DRUG HYDROXYLATION; DRUG METABOLISM; DRUG OXIDATION; FUNGAL METABOLISM; FUNGAL STRAIN; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; UMBELOPSIS RAMANNIANA;

ANTICONVULSANTS; BIOTRANSFORMATION; CARBAMAZEPINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; KINETICS; MASS SPECTROMETRY; MUCORALES;

CAENORHABDITIS ELEGANS; CUNNINGHAMELLA ELEGANS; FUNGI; MAMMALIA; RATTUS; UMBELOPSIS RAMANNIANA;

EID: 44649153681     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-008-1459-5     Document Type: Article

References (33)

1. Azerad R (1999) Microbial models for drug metabolism. Adv Biochem Eng Biotech 63:169-218
2. Castiglioni S, Bagnati R, Fanelli R, Pomati F, Calamari D, Zuccato E (2006) Removal of pharmaceuticals in sewage treatment plants in Italy. Environ Sci Technol 40:357-363
3. Duhart BTJ, Zhang D, Deck J, Freeman JP, Cerniglia CE (1999) Biotransformation of protriptyline by filamentous fungi and yeasts. Xenobiotica 29:733-746
4. Faigle JW, Feldmann KF (1989) Carbamazepine. Chemistry and biotransformation. In: Levy R, Mattson R, Meldrum BS, Penry JK, Dreifuss FE (eds) Antiepiletic drugs. 3rd edn. Raven, New York, pp 499-513
5. Faigle JW, Feldmann KF (1995) Carbamazepine. Chemistry and biotransformation. In: Levy R, Mattson R, Meldrum BS (eds) Antiepiletic drugs. 4th edn. Raven, New York, pp 499-513
6. Han GH, Hur HG, Kim SD (2006) Ecotoxicological risk of pharmaceuticals from wastewater treatment plants in Korea: occurrence and toxicity to Daphnia magna. Environ Toxicol Chem 25:265-271
7. Hufford CD, Capiton GA, Clark AM, Baker JK (1981) Metabolism of imipramine by microorganisms. J Pharma Sci 70:151-155
8. Kerr BM, Thummel KE, Wurden CJ, Klein SM, Kroetz DL, Gonzalez FL, Levy RH (1994) Human liver carbamazepine metabolism: role of CYP3A4 and CYP2C8 in 10,11-epoxide formation. Biochem Pharmacol 47:1969-1979
9. Kittelmann M, Lattmann R, Ghisalba O (1993) Preparation of 10,11-epoxy-carbamazepine and 10,11-dihydro-10-hydroxy-carbamazepine by microbial epoxidation and hydroxylation. Biosci Biotechnol Biochem 57:1589-1590
10. Kitteringham NR, Davis C, Howard N, Pirmohamed M, Park BK (1996) Interindividual and interspecies variation in hepatic microsomal epoxide hydrolase activity: studies with cis-stilbene oxide, carbamazepine 10,11-epoxide and naphthalene. J Pharmacol Exp Ther 278:1018-1027
11. Lertratanangkoon K, Horning MG (1982) Metabolism of carbamazepine. Drug Metab Dispos 10:1-10
12. Loffler D, Rombke J, Meller M, Ternes T (2005) Environmental fate of pharmaceuticals in water/sediment systems. Environ Sci Technol 39:5209-5218
13. Lynn RK, Smith RG, Thompson RM, Deinzer ML, Griffin D, Gerber N (1978) Characterization of glucuronide metabolites of carbamazepine in human urine by gas chromatography and mass spectrometry. Drug Metab Dispos 6:494-501
14. Maggs JL, Pirmohamed M, Kitteringham NR, Park BK (1997) Characterization of the metabolites of carbamazepine in patient urine by liquid chromatography/mass spectrometry. Drug Metab Dispos 25:275-280
15. Miao X, Metcalfe CD (2003) Determination of carbamazepine and its metabolites in aqueous samples using liquid chromatography-electrospray tandem mass spectrometry. Anal Chem 75:3731-3738
16. Moody JD, Freeman JP, Cerniglia CE (1999) Biotransformation of doxepin by Cunninghamella elegans. Drug Metab Dispos 27:1157-1164
17. Myllynen P, Pienimaki P, Raunio H, Vahakangas K (1998) Microsomal metabolism of carbamazepine and oxcarbamazepine in liver and placenta. Human Exp Toxicol 17:668-676
18. Ogawa Y, Suda A, Kusama-Eguchi K, Watanabe K, Tokumasu S (2005) Interspecific groups of Umbelopsis ramanniana inferred from nucleotide sequences of nuclear rDNA transcribed spacer regions and sporangiospore morphology. Mycoscience 46:343-351
19. Parshikov IA, Freeman JP, Lay JO Jr, Beger RD, Williams AJ, Sutherland JB (1999) Regioselective transformation of ciprofloxacin to N-acetylciprofloxacin by the fungus Mucor ramannianus. FEMS Microbiol Lett 177:131-135
20. Parshikov IA, Freeman JP, Lay JO Jr, Beger RD, Williams AJ, Sutherland JB (2000) Microbiological transformation of enrofloxacin by the fungus Mucor ramannianus. Appl Environ Microbiol 66:2664-2667
21. Parshikov IA, Miriyala B, Muraleedharan K, Illendula A, Avery M, Williams J (2005) Biocatalysis of the antimalarial artemisinin by Mucor ramannianus strains. Pharma Biol 43:579-582
22. Pelkonen O, Myllynen P, Taavitsainen P, Boobis AR, Watts P, Lake BG, Price RJ, Renwick AB, Gomez-Lechon MJ, Castell JV, Ingelman-Sundberg M, Hidestrand M, Guillouzo A, Corcos L, Goldfarb PS, Lewis DF (2001) Carbamazepine: a 'blind' assessment of CVP-associated metabolism and interactions in human liver-derived in vitro systems. Xenobiotica 31:321-343
23. Seo J, Lee Y-G, Kim S-D, Cha C-J, Ahn J-H, Hur H-G (2005) Biodegradation of the insecticide N,N,-Diethyl-m-toluamide by fungi: identification and toxicity of metabolites. Arch Environ Contam Toxicol 48:323-328
24. Seo J, Jeon J, Kim S-D, Kang S, Han J, Hur H-G (2007) Fungal biodegradation of carbofuran and carbofuran phenol by the fungus Mucor ramannianus: identification of metabolites. Water Sci Technol 55:163-167
25. Staines AG, Michael WHC, Burchell B (2004) N-Glucuronidation of carbamazepine in human tissues is mediated by UGT2B7. J Pharmacol Exp Ther 311:1131-1137
26. Ternes TA (1998) Occurrence of drugs in German sewage treatment plants and rivers. Water Res 32:3245-3260
27. Tixier C, Singer H, Oellers S, Muller SR (2003) Occurrence and fate of carbamazepine, clofibric acid, diclofenac, ibuprofen, ketoprofen and naproxen in surface waters. Environ Sci Technol 37:1061-1068
28. Valentine CR, Valentine JL, Seng J, Leakey J, Casciano D (1996) The use of transgenic cell lines for evaluating toxic metabolites of carbamazepine. Cell Biol Toxicol 12:155-165
29. Zhang D, Evans FE, Freeman JP, Duhart BJR, Cerniglia CE (1995) Biotransformation of amitriptyline by Cunninghamella elegans. Drug Metab Dispos 23:1417-1425
30. Zhang D, Evans FE, Freeman JP, Yang Y, Deck J, Cerniglia CE (1996a) Formation of mammalian metabolites of cyclobenzaprine by the fungus, Cunninghamella elegans. Chem Biol Interactions 102:79-92
31. Zhang D, Hansen EB, Deck JJR, Heinze TM, Sutherland JB, Cerniglia CE (1996b) Fungal biotransformation of the antihistamine azatadine by Cunninghamella elegans. Appl Environ Microbiol 62:3477-3479
32. Zhang D, Yifan Y, Leakey JEA, Cerniglia CE (1996c) Phase I and phase II enzymes produced by Cunninghamella elegans for the metabolism of xenobiotics. FEMS Micobiol Lett 138:221-226
33. Zhang D, Hansen EB, Deck JJR, Heinze TM, Henderson A, Korfmacher WA, Cerniglia CE (1997) Fungal transformation of antihistamines: metabolism of cyproheptadine hydrochloride by Cunninghamella elegans. Xenobiotica 27:310-315