Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 17, 1987 - Issue 7
141
Views
52
CrossRef citations to date
0
Altmetric
Original Article

Biotransformation of ketamine, (Z)-6-hydroxyketamine, and (E)-6-hydroxyketamine by rat, rabbit, and human liver microsomal preparations

&
Pages 839-847 | Received 18 Jun 1986, Published online: 30 Sep 2009

Keep up to date with the latest research on this topic with citation updates for this article.

Read on this site (3)

Ricardo Jorge Dinis-Oliveira. (2017) Metabolism and metabolomics of ketamine: a toxicological approach. Forensic Sciences Research 2:1, pages 2-10.
Read now
Zeruesenay Desta, Ruin Moaddel, Evan T. Ogburn, Cong Xu, Anuradha Ramamoorthy, Swarajya Lakshmi Vattem Venkata, Mitesh Sanghvi, Michael E. Goldberg, Marc C. Torjman & Irving W. Wainer. (2012) Stereoselective and regiospecific hydroxylation of ketamine and norketamine. Xenobiotica 42:11, pages 1076-1087.
Read now
Ingeborg Noppers, Marieke Niesters, Leon Aarts, Terry Smith, Elise Sarton & Albert Dahan. (2010) Ketamine for the treatment of chronic non-cancer pain. Expert Opinion on Pharmacotherapy 11:14, pages 2417-2429.
Read now

Articles from other publishers (49)

Xuan Luo, Di Zhang, Fang Zhang, Qiulian Luo, Kejian  Huang, Xiaofeng Liu, Ning Yang, Junbo Li, Wentao Qiao & Lan Yang. (2023) Comparative Analysis and Structure Identification of Oxidative Metabolites and Hydrogenation Metabolite Enantiomers for 2-Fluorodeschloroketamine. Journal of Analytical Toxicology 47:5, pages 436-447.
Crossref
Thi Mai Loan Nguyen, Josephine Cecelia McGowan & Alain M. Gardier. (2022) CYP 450 enzymes influence (R,S)-ketamine brain delivery and its antidepressant activity. Neuropharmacology 206, pages 108936.
Crossref
Jaclyn N Highland, Cristan A Farmer, Panos Zanos, Jacqueline Lovett, Carlos A ZarateJr.Jr., Ruin Moaddel & Todd D Gould. (2021) Sex-dependent metabolism of ketamine and ( 2R,6R )-hydroxynorketamine in mice and humans . Journal of Psychopharmacology 36:2, pages 170-182.
Crossref
Lena V. Danyeli, Florian N. Götting, Zümrüt Duygu Sen, Meng Li & Martin Walter. 2022. NeuroPsychopharmacotherapy. NeuroPsychopharmacotherapy 4593 4635 .
Jaclyn N. Highland, Panos Zanos, Lace M. Riggs, Polymnia Georgiou, Sarah M. Clark, Patrick J. Morris, Ruin Moaddel, Craig J. Thomas, Carlos A. ZarateJr.Jr., Edna F. R. Pereira & Todd D. Gould. (2021) Hydroxynorketamines: Pharmacology and Potential Therapeutic Applications. Pharmacological Reviews 73:2, pages 763-791.
Crossref
Samuel Kohtala. (2021) Ketamine—50 years in use: from anesthesia to rapid antidepressant effects and neurobiological mechanisms. Pharmacological Reports 73:2, pages 323-345.
Crossref
Lena V. Danyeli, Florian N. Götting, Zümrüt Duygu Sen, Meng Li & Martin Walter. 2020. NeuroPsychopharmacotherapy. NeuroPsychopharmacotherapy 1 44 .
Rebecca McMillan & Suresh D. Muthukumaraswamy. (2020) The neurophysiology of ketamine: an integrative review. Reviews in the Neurosciences 31:5, pages 457-503.
Crossref
Cristan A. Farmer, Jessica R. Gilbert, Ruin Moaddel, Jomy George, Lilian Adeojo, Jacqueline Lovett, Allison C. Nugent, Bashkim Kadriu, Peixiong Yuan, Todd D. Gould, Lawrence T. Park & Carlos A. ZarateJr.Jr.. (2020) Ketamine metabolites, clinical response, and gamma power in a randomized, placebo-controlled, crossover trial for treatment-resistant major depression. Neuropsychopharmacology 45:8, pages 1398-1404.
Crossref
Jaclyn N Highland, Patrick J Morris, Panos Zanos, Jacqueline Lovett, Soumita Ghosh, Amy Q Wang, Carlos A ZarateJrJr, Craig J Thomas, Ruin Moaddel & Todd D Gould. (2018) Mouse, rat, and dog bioavailability and mouse oral antidepressant efficacy of ( 2R,6R )-hydroxynorketamine . Journal of Psychopharmacology 33:1, pages 12-24.
Crossref
Panos Zanos, Ruin Moaddel, Patrick J. Morris, Lace M. Riggs, Jaclyn N. Highland, Polymnia Georgiou, Edna F. R. Pereira, Edson X. Albuquerque, Craig J. Thomas, Carlos A. ZarateJr.Jr. & Todd D. Gould. (2018) Ketamine and Ketamine Metabolite Pharmacology: Insights into Therapeutic Mechanisms. Pharmacological Reviews 70:3, pages 621-660.
Crossref
Tuomas O. Lilius, Hanna Viisanen, Viljami Jokinen, Mikko Niemi, Eija A. Kalso & Pekka V. Rauhala. (2018) Interactions of (2S,6S;2R,6R)-Hydroxynorketamine, a Secondary Metabolite of (R,S)-Ketamine, with Morphine. Basic & Clinical Pharmacology & Toxicology 122:5, pages 481-488.
Crossref
Cato Veen, Gabriel Jacobs, Ingrid Philippens & Eric Vermetten. 2018. Behavioral Neurobiology of PTSD. Behavioral Neurobiology of PTSD 137 162 .
Bonnie L. Robinson, Melanie Dumas, Syed F. Ali, Merle G. Paule, Qiang Gu & Jyotshna Kanungo. (2017) Cyclosporine exacerbates ketamine toxicity in zebrafish: Mechanistic studies on drug-drug interaction. Journal of Applied Toxicology 37:12, pages 1438-1447.
Crossref
Robert B. Flint, Carole N. M. Brouwer, Anne S. C. Kränzlin, Loraine Lie-A-Huen, Albert P. Bos & Ron A. A. Mathôt. (2017) Pharmacokinetics of S-ketamine during prolonged sedation at the pediatric intensive care unit. Pediatric Anesthesia 27:11, pages 1098-1107.
Crossref
Rae Frances Bell, Christopher Eccleston & Eija A Kalso. (2017) Ketamine as an adjuvant to opioids for cancer pain. Cochrane Database of Systematic Reviews 2019:9.
Crossref
Marshall W. Tyler, Harmony B. Yourish, Dawn F. Ionescu & Stephen J. Haggarty. (2017) Classics in Chemical Neuroscience: Ketamine. ACS Chemical Neuroscience 8:6, pages 1122-1134.
Crossref
Vesna Cerkvenik Flajs & James D. MacNeil. 2016. Chemical Analysis of Non&;#x02010;antimicrobial Veterinary Drug Residues in Food. Chemical Analysis of Non&;#x02010;antimicrobial Veterinary Drug Residues in Food 311 381 .
Marko A. Peltoniemi, Nora M. Hagelberg, Klaus T. Olkkola & Teijo I. Saari. (2016) Ketamine: A Review of Clinical Pharmacokinetics and Pharmacodynamics in Anesthesia and Pain Therapy. Clinical Pharmacokinetics 55:9, pages 1059-1077.
Crossref
Luís Félix, Luís Antunes, Sónia Campos, Carlos Venâncio & Ana Maria Coimbra. 2016. Neuropathology of Drug Addictions and Substance Misuse. Neuropathology of Drug Addictions and Substance Misuse 672 680 .
Kinga Sałat, Agata Siwek, Gabriela Starowicz, Tadeusz Librowski, Gabriel Nowak, Urszula Drabik, Ryszard Gajdosz & Piotr Popik. (2015) Antidepressant-like effects of ketamine, norketamine and dehydronorketamine in forced swim test: Role of activity at NMDA receptor. Neuropharmacology 99, pages 301-307.
Crossref
Rajib K. PaulNagendra S. SinghMohammed KhadeerRuin MoaddelMitesh SanghviCarol E. GreenKathleen O’LoughlinMarc C. TorjmanMichel BernierIrving W. Wainer. (2014) ( R,S )-Ketamine Metabolites ( R,S )-norketamine and ( 2S,6S )-hydroxynorketamine Increase the Mammalian Target of Rapamycin Function . Anesthesiology 121:1, pages 149-159.
Crossref
Angela Yu-Chen Lin, Wan-Ning Lee & Xiao-Huan Wang. (2014) Ketamine and the metabolite norketamine: Persistence and phototransformation toxicity in hospital wastewater and surface water. Water Research 53, pages 351-360.
Crossref
Marieke Niesters, Christian Martini & Albert Dahan. (2014) Ketamine for chronic pain: risks and benefits. British Journal of Clinical Pharmacology 77:2, pages 357-367.
Crossref
Francesca Sori, Noemi Romagnoli, Domenico Ferrara, Anna Zaghini & Paola Roncada. (2013) Plasma and Red Blood Cells Concentration Profiles of Ktamine after Single Intravenous Administration in an Anaesthetic Protocol in Horses. Open Journal of Veterinary Medicine 03:02, pages 136-142.
Crossref
L.M. Peters, S. Demmel, G. Pusch, J.T.M. Buters, W. Thormann, J. Zielinski, T. Leeb, M. Mevissen & A. Schmitz. (2013) Equine cytochrome P450 2B6 — Genomic identification, expression and functional characterization with ketamine. Toxicology and Applied Pharmacology 266:1, pages 101-108.
Crossref
Andrew A. Somogyi & Janet K. Coller. 2012. Metabolism of Drugs and Other Xenobiotics. Metabolism of Drugs and Other Xenobiotics 403 428 .
Lone D. Mössner, Andrea Schmitz, Regula Theurillat, Wolfgang Thormann & Meike Mevissen. (2011) Inhibition of cytochrome P450 enzymes involved in ketamine metabolism by use of liver microsomes and specific cytochrome P450 enzymes from horses, dogs, and humans. American Journal of Veterinary Research 72:11, pages 1505-1513.
Crossref
Hiu Ying Kwan & Wolfgang Thormann. (2011) Enantioselective capillary electrophoresis for the assessment of CYP3A4-mediated ketamine demethylation and inhibition in vitro. ELECTROPHORESIS 32:19, pages 2738-2745.
Crossref
Simone Portmann, Hiu Ying Kwan, Regula Theurillat, Andrea Schmitz, Meike Mevissen & Wolfgang Thormann. (2010) Enantioselective capillary electrophoresis for identification and characterization of human cytochrome P450 enzymes which metabolize ketamine and norketamine in vitro. Journal of Chromatography A 1217:51, pages 7942-7948.
Crossref
Ruin Moaddel, Swarajya Lakshmi Vattem Venkata, Mary J. Tanga, James E. Bupp, Carol E. Green, Lalitha Iyer, Anna Furimsky, Michael E. Goldberg, Marc C. Torjman & Irving W. Wainer. (2010) A parallel chiral–achiral liquid chromatographic method for the determination of the stereoisomers of ketamine and ketamine metabolites in the plasma and urine of patients with complex regional pain syndrome. Talanta 82:5, pages 1892-1904.
Crossref
Andrea Schmitz, Wolfgang Thormann, Lone Moessner, Regula Theurillat, Kati Helmja & Meike Mevissen. (2010) Enantioselective CE analysis of hepatic ketamine metabolism in different species in vitro . ELECTROPHORESIS, pages NA-NA.
Crossref
Fernando SF Cruz, Adriano B Carregaro, Alceu G Raiser, Marina Zimmerman, Rafael Lukarsewski & Renata PB Steffen. (2010) Total intravenous anesthesia with propofol and S(+)-ketamine in rabbits. Veterinary Anaesthesia and Analgesia 37:2, pages 116-122.
Crossref
Sophie C. Turfus, Mark C. Parkin, David A. Cowan, John M. Halket, Norman W. Smith, Robin A. Braithwaite, Simon P. Elliot, Glyn B. Steventon & Andrew T. Kicman. (2009) Use of Human Microsomes and Deuterated Substrates: An Alternative Approach for the Identification of Novel Metabolites of Ketamine by Mass Spectrometry. Drug Metabolism and Disposition 37:8, pages 1769-1778.
Crossref
Andrea Schmitz, Regula Theurillat, Paul-Gerhard Lassahn, Meike Mevissen & Wolfgang Thormann. (2009) CE provides evidence of the stereoselective hydroxylation of norketamine in equines. ELECTROPHORESIS 30:16, pages 2912-2921.
Crossref
Jenny L. Wiley, Rhys L. Evans, Darren B. Grainger & Katherine L. Nicholson. (2008) Age-dependent differences in sensitivity and sensitization to cannabinoids and ‘club drugs’ in male adolescent and adult rats. Addiction Biology 13:3-4, pages 277-286.
Crossref
M.P. Larenza, M.F. Landoni, O.L. Levionnois, M. Knobloch, P.W. Kronen, R. Theurillat, U. Schatzmann & W. Thormann. (2007) Stereoselective pharmacokinetics of ketamine and norketamine after racemic ketamine or S-ketamine administration during isoflurane anaesthesia in Shetland ponies. British Journal of Anaesthesia 98:2, pages 204-212.
Crossref
Yoshitsugu Yanagihara. (2006) Studies on Development and Clinical Application of Ketamine Preparations for Neuropathic Pain Relief. Iryo Yakugaku (Japanese Journal of Pharmaceutical Health Care and Sciences) 32:4, pages 275-288.
Crossref
Bruno H. Pypendop & Jan E. Ilkiw. (2005) Pharmacokinetics of ketamine and its metabolite, norketamine, after intravenous administration of a bolus of ketamine to isoflurane-anesthetized dogs. American Journal of Veterinary Research 66:12, pages 2034-2038.
Crossref
Gert Luurtsema, Carla F.M. Molthoff, Robert C. Schuit, Albert D. Windhorst, Adriaan A. Lammertsma & Eric J.F. Franssen. (2005) Evaluation of (R)-[11C]verapamil as PET tracer of P-glycoprotein function in the blood–brain barrier: kinetics and metabolism in the rat. Nuclear Medicine and Biology 32:1, pages 87-93.
Crossref
Y. Hijazi, C. Bodonian, M. Bolon, F. Salord & R. Boulieu. (2003) Pharmacokinetics and haemodynamics of ketamine in intensive care patients with brain or spinal cord injury. British Journal of Anaesthesia 90:2, pages 155-160.
Crossref
Youssef Hijazi & Roselyne Boulieu. (2002) Contribution of CYP3A4, CYP2B6, and CYP2C9 Isoforms to N- Demethylation of Ketamine in Human Liver Microsomes . Drug Metabolism and Disposition 30:7, pages 853-858.
Crossref
S.R. Edwards, C.F. Minto & L.E. Mather. (2002) Concurrent ketamine and alfentanil administration: pharmacokinetic considerations. British Journal of Anaesthesia 88:1, pages 94-100.
Crossref
Laura A Egnash & Ragu Ramanathan. (2002) Comparison of heterogeneous and homogeneous radioactivity flow detectors for simultaneous profiling and LC-MS/MS characterization of metabolites. Journal of Pharmaceutical and Biomedical Analysis 27:1-2, pages 271-284.
Crossref
Sean Ekins, Jukka Maenpää & Steven Wrighton. 1999. Handbook of Drug Metabolism. Handbook of Drug Metabolism 363 399 .
Megumi Shimoyama, Naohito Shimoyama, Charles E. Inturrisi & Kathryn Elliott. (1996) Oral ketamine produces a dose-dependent CNS depression in the rat. Life Sciences 60:1, pages PL9-PL14.
Crossref
G. Geisslinger, S. Menzel-Soglowek, H.-D. Kamp & K. Brune. (1991) Stereoselective high-performance liquid chromatographic determination of the enantiomers of ketamine and norketamine in plasma. Journal of Chromatography B: Biomedical Sciences and Applications 568:1, pages 165-176.
Crossref
Louis Y. Leung & Thomas A. Baillie. (1989) Studies on the biotransformation of ketamine. II—quantitative significance of theN-demethylation pathway in ratsin vivo determined by a novel stable isotope technique. Biological Mass Spectrometry 18:6, pages 401-404.
Crossref
A. L. Burlingame, D. Maltby, D. H. Russell & P. T. Holland. (2002) Mass spectrometry. Analytical Chemistry 60:12, pages 294-342.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.