ケタミン

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ケタミン
(S)-Ketamine ball-and-stick model
Systematic (IUPAC) name
(RS)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone
Clinical data
Trade names Ketalar, others
AHFS/Drugs.com monograph
Licence data US Daily Med:link
Pregnancy cat. B3 (AU) ? (US)
Legal status Controlled (S8) (AU) Schedule I (CA) ? (UK) Schedule III (US) Prescription only
Routes Any[1][2][3]
Pharmacokinetic data
Bioavailability * Intravenous: 100%[3]

[10]

Protein binding 12–47% (low)[5][7][12]
Metabolism Liver (N-demethylation):[3][13]
Half-life * Ketamine: 2.5–3 hours[7][3]
  • Norketamine: 12 hours[14]
Excretion * Urine: 91%[3]
Identifiers
CAS number 6740-88-1 YesY
ATC code N01AX03
PubChem CID 3821
IUPHAR ligand 4233
DrugBank DB01221
ChemSpider 3689 YesY
UNII 690G0D6V8H YesY
KEGG D08098 YesY
ChEBI CHEBI:6121 YesY
ChEMBL CHEMBL742 YesY
Synonyms CI-581; CL-369; CM-52372-2[15]
Chemical data
Formula C13H16ClNO 
Mol. mass 237.725
Physical data
Melt. point 258–261 °C (496–502 °F)
 YesY (what is this?)  (verify)
  1. Bell, R.F., Eccleston, C., & Kalso, E.A. (2017).
    Ketamine as an adjuvant to opioids for cancer pain. The Cochrane database of systematic reviews, 6, CD003351. [PubMed:28657160] [PMC] [WorldCat] [DOI]
  2. Moyse, D.W., Kaye, A.D., Diaz, J.H., Qadri, M.Y., Lindsay, D., & Pyati, S. (2017).
    Perioperative Ketamine Administration for Thoracotomy Pain. Pain physician, 20(3), 173-184. [PubMed:28339431] [WorldCat]
  3. 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8 Frohlich, J., & Van Horn, J.D. (2014).
    Reviewing the ketamine model for schizophrenia. Journal of psychopharmacology (Oxford, England), 28(4), 287-302. [PubMed:24257811] [PMC] [WorldCat] [DOI]
  4. Jianren Mao. (2016).
    Opioid-Induced Hyperalgesia
    CRC Press
  5. 5.0 5.1 5.2 Pascal Kintz. (2014).
    Toxicological Aspects of Drug-Facilitated Crimes
    Elsevier Science
  6. Molero, P., Ramos-Quiroga, J.A., Martin-Santos, R., Calvo-Sánchez, E., Gutiérrez-Rojas, L., & Meana, J.J. (2018).
    Antidepressant Efficacy and Tolerability of Ketamine and Esketamine: A Critical Review. CNS drugs, 32(5), 411-420. [PubMed:29736744] [WorldCat] [DOI]
  7. 7.0 7.1 7.2 Sinner, B., & Graf, B.M. (2008).
    Ketamine. Handbook of experimental pharmacology, (182), 313-33. [PubMed:18175098] [WorldCat] [DOI]
  8. Hashimoto, K. (2019).
    Rapid-acting antidepressant ketamine, its metabolites and other candidates: A historical overview and future perspective. Psychiatry and clinical neurosciences, 73(10), 613-627. [PubMed:31215725] [PMC] [WorldCat] [DOI]
  9. Alan F. Schatzberg & Charles B. Nemeroff. (2017).
    The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition
    American Psychiatric Pub, pp550-.
  10. 10.0 10.1 Zhang, K., & Hashimoto, K. (2019).
    An update on ketamine and its two enantiomers as rapid-acting antidepressants. Expert review of neurotherapeutics, 19(1), 83-92. [PubMed:30513009] [WorldCat] [DOI]
  11. Andrew Dickman & Jennifer Schneider. (2016).
    The Syringe Driver: Continuous Subcutaneous Infusions in Palliative Care
    Oxford University Press, pp. 114-
  12. Frank J. Dowd, Bart Johnson & Angelo Mariotti. (2016).
    Pharmacology and Therapeutics for Dentistry – E-Book
    Elsevier Health Sciences, pp235–
  13. Hijazi, Y., & Boulieu, R. (2002).
    Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes. Drug metabolism and disposition: the biological fate of chemicals, 30(7), 853-8. [PubMed:12065445] [WorldCat] [DOI]
  14. Quibell, R., Prommer, E.E., Mihalyo, M., Twycross, R., & Wilcock, A. (2011).
    Ketamine*. Journal of pain and symptom management, 41(3), 640-9. [PubMed:21419322] [WorldCat] [DOI]
  15. I.K. Morton, & Judith M. Hall. (2012).
    Concise Dictionary of Pharmacological Agents: Properties and Synonyms
    Springer Science & Business Media, pp159–