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Chemical Compound Review

norketamine     2-amino-2-(2- chlorophenyl)cyclohexan-1-one

Synonyms: CHEMBL1039, AGN-PC-00FX4J, SureCN3390132, CTK8D6626, AR-1D8132, ...
 
 
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Disease relevance of norketamine

 

High impact information on norketamine

 

Biological context of norketamine

  • These results demonstrate that a significant amount of norketamine is formed by first pass biotransformation of ketamine and is distributed to the brain [7].
  • Plasma concentrations of ketamine and norketamine were measured in eight children and revealed a pharmacokinetic pattern indicating comparatively low bioavailability probably due to incomplete absorption from the rectum and a high 'first-pass' metabolism [8].
  • No-carrier-added (NCA)[11C](+/-)-ketamine (2a) and its enantiomers (+)-2b and (-)-2c were synthesized by methylation of the corresponding norketamine (1a-c) with [11C]H3I in an overall radiochemical yield of 20% (EOB) with specific activities of 0.35-0.45 Ci/mumol at EOB in a synthesis time of 40 min from EOB [9].
  • Acidic hydrolysis of urine samples resulted in the detection of a significant increase of K, NK, and DHNK [10].
  • We performed a study in rats with two complementary paradigms: (i) constant rate "washin" infusion until fatal, (ii) brief infusion then "washout". These, respectively, allowed examination of ketamine and norketamine serial plasma enantiomer concentrations and tissue distribution at maximal and minimal drug effects [11].
 

Anatomical context of norketamine

 

Associations of norketamine with other chemical compounds

 

Gene context of norketamine

  • A decrease in the clearance of both NKET enantiomers led to a significant increase in exposure in PCM rats (p < 0.005), and modeling results could not exclude the possibility that PCM induced an increase in the fraction of KET following the NKET pathway, which may further contribute to this increase in exposure [5].
  • One aim of this paper was to study the elimination of KET and its major metabolite norketamine (NKET) in urine collected from five nonhuman primates that received a single dose (5 mg/kg, I.M.) of KET and to study elimination patterns to determine how long after drug administration KET and NKET can be detected [13].
  • After oral ingestion, ketamine is metabolized into norketamine, which in vitro possesses NMDA receptor antagonistic effect [14].
 

Analytical, diagnostic and therapeutic context of norketamine

References

  1. Ketamine and midazolam kinetics during continuous hemodiafiltration in patients with multiple organ dysfunction syndrome. Tsubo, T., Sakai, I., Okawa, H., Ishihara, H., Matsuki, A. Intensive care medicine. (2001) [Pubmed]
  2. Characterization of the stereoselective biotransformation of ketamine to norketamine via determination of their enantiomers in equine plasma by capillary electrophoresis. Theurillat, R., Knobloch, M., Levionnois, O., Larenza, P., Mevissen, M., Thormann, W. Electrophoresis (2005) [Pubmed]
  3. HPLC determination of ketamine, norketamine, and dehydronorketamine in plasma with a high-purity reversed-phase sorbent. Bolze, S., Boulieu, R. Clin. Chem. (1998) [Pubmed]
  4. Stereoselective pharmacokinetics of ketamine and norketamine after racemic ketamine or S-ketamine administration during isoflurane anaesthesia in Shetland ponies. Larenza, M.P., Landoni, M.F., Levionnois, O.L., Knobloch, M., Kronen, P.W., Theurillat, R., Schatzmann, U., Thormann, W. British journal of anaesthesia (2007) [Pubmed]
  5. Effects of protein calorie malnutrition on the pharmacokinetics of ketamine in rats. Williams, M.L., Mager, D.E., Parenteau, H., Gudi, G., Tracy, T.S., Mulheran, M., Wainer, I.W. Drug Metab. Dispos. (2004) [Pubmed]
  6. Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes. Hijazi, Y., Boulieu, R. Drug Metab. Dispos. (2002) [Pubmed]
  7. Oral ketamine is antinociceptive in the rat formalin test: role of the metabolite, norketamine. Shimoyama, M., Shimoyama, N., Gorman, A.L., Elliott, K.J., Inturrisi, C.E. Pain (1999) [Pubmed]
  8. Rectal ketamine for induction of anaesthesia in children. Idvall, J., Holasek, J., Stenberg, P. Anaesthesia. (1983) [Pubmed]
  9. Carbon-11 labelled ketamine-synthesis, distribution in mice and PET studies in baboons. Shiue, C.Y., Vallabhahosula, S., Wolf, A.P., Dewey, S.L., Fowler, J.S., Schlyer, D.J., Arnett, C.D., Zhou, Y.G. Nucl. Med. Biol. (1997) [Pubmed]
  10. Detection of acid-labile conjugates of ketamine and its metabolites in urine samples collected from pub participants. Lin, H.R., Lua, A.C. Journal of analytical toxicology. (2004) [Pubmed]
  11. Tissue uptake of ketamine and norketamine enantiomers in the rat: indirect evidence for extrahepatic metabolic inversion. Edwards, S.R., Mather, L.E. Life Sci. (2001) [Pubmed]
  12. Ketamine and midazolam decrease cerebral blood flow and consequently their own rate of transport to the brain: an application of mass balance pharmacokinetics with a changing regional blood flow. Björkman, S., Akeson, J., Nilsson, F., Messeter, K., Roth, B. Journal of pharmacokinetics and biopharmaceutics. (1992) [Pubmed]
  13. Detection of ketamine and norketamine in urine of nonhuman primates after a single dose of ketamine using microplate enzyme-linked immunosorbent assay (ELISA) and NCI-GC-MS. Negrusz, A., Adamowicz, P., Saini, B.K., Webster, D.E., Juhascik, M.P., Moore, C.M., Schlemmer, R.F. Journal of analytical toxicology. (2005) [Pubmed]
  14. Effect of oral ketamine on secondary hyperalgesia, thermal and mechanical pain thresholds, and sedation in humans. Mikkelsen, S., Jørgensen, H., Larsen, P.S., Brennum, J., Dahl, J.B. Regional anesthesia and pain medicine. (2000) [Pubmed]
  15. Role of chiral chromatography in therapeutic drug monitoring and in clinical and forensic toxicology. Williams, M.L., Wainer, I.W. Therapeutic drug monitoring. (2002) [Pubmed]
  16. Pharmacokinetics and analgesic effects of i.m. and oral ketamine. Grant, I.S., Nimmo, W.S., Clements, J.A. British journal of anaesthesia. (1981) [Pubmed]
  17. On-line preconcentration and determination of ketamine and norketamine by micellar electrokinetic chromatography. Complementary method to gas chromatography/mass spectrometry. Jen, H.P., Tsai, Y.C., Su, H.L., Hsieh, Y.Z. Journal of chromatography. A. (2006) [Pubmed]
  18. Ketamine and norketamine plasma concentrations after i.v., nasal and rectal administration in children. Malinovsky, J.M., Servin, F., Cozian, A., Lepage, J.Y., Pinaud, M. British journal of anaesthesia. (1996) [Pubmed]
  19. Use of SPE and LC/TIS/MS/MS for rapid detection and quantitation of ketamine and its metabolite, norketamine, in urine. Wang, K.C., Shih, T.S., Cheng, S.G. Forensic Sci. Int. (2005) [Pubmed]
 
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