Identification of fungal metabolites of anticonvulsant drug carbamazepine

Applied Microbiology and Biotechnology
Su-Il KangHor-Gil Hur

Abstract

Carbamazepine, which has been used in the treatments of epilepsy, is often found in the environment. Although metabolism of carbamazepine by humans and rats has been characterized, the environmental fate of carbamazepine has not been studied. In this study, two model fungi Cunninghamella elegans ATCC 9245 and Umbelopsis ramanniana R-56, which have previously shown diverse metabolic activities, were tested for metabolism of carbamazepine. Both fungi produced three metabolites each (C1-C3 and M1-M3). All six metabolites showed [M + H](+) at m/z 253, suggesting addition of one oxygen to the parent compound. High-performance liquid chromatography and liquid chromatography-mass spectrometric analysis detected 10, 11-dihydro-10, 11-epoxycarbamazepine as a major product (C3 (47%) and M3 (85%)) and 3-hydroxycarbamazepine (C2 (15%) and M2 (7%)) from carbamazepine through mixed mono-oxidation reactions in both fungal strains. C. elegans was confirmed to produce 2-hydroxycarbamazepine (C1 (38%)) while U. ramanniana produced a yet unidentified ring-hydroxylated metabolite (M1 (8%)). The current study suggests that carbamazepine is likely to be subjected to initially diverse mono-oxygenation reactions by fungal metabolisms, resulting in the...Continue Reading

References

Sep 1, 1982·Drug and Alcohol Dependence·T L Cameron
Feb 1, 1981·Journal of Pharmaceutical Sciences·C D HuffordJ K Baker
Sep 1, 1996·Applied and Environmental Microbiology·D ZhangC E Cerniglia
Jun 1, 1996·Cell Biology and Toxicology·C R ValentineD Casciano
Oct 21, 1996·Chemico-biological Interactions·D ZhangC E Cerniglia
Mar 1, 1997·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·D ZhangC E Cerniglia
Feb 13, 1999·Human & Experimental Toxicology·P MyllynenK Vähäkangas
Aug 24, 1999·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·B T DuhartC E Cerniglia
Jun 1, 2000·Applied and Environmental Microbiology·I A ParshikovJ B Sutherland
Aug 22, 2001·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·O PelkonenD F Lewis
Apr 12, 2003·Environmental Science & Technology·Céline TixierStephan R Müller
Aug 5, 2004·The Journal of Pharmacology and Experimental Therapeutics·Adam G StainesBrian Burchell
Mar 8, 2005·Archives of Environmental Contamination and Toxicology·J SeoH-G Hur
Aug 9, 2005·Environmental Science & Technology·Dirk LöfflerThomas A Ternes
Jan 26, 2006·Environmental Science & Technology·Sara CastiglioniEttore Zuccato
Feb 20, 2007·Water Science and Technology : a Journal of the International Association on Water Pollution Research·Jiyoung SeoHor-Gil Hur

❮ Previous
Next ❯

Citations

Feb 19, 2011·The Analyst·Arnold BahlmannRudolf J Schneider
Dec 24, 2014·Journal of Pharmaceutical and Biomedical Analysis·Anna Barra CaraccioloPaola Grenni
Oct 6, 2017·Frontiers in Microbiology·Darío R Olicón-HernándezElisabet Aranda

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.