ケタミン

ケタミン
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
Pharmacokinetic data
Bioavailability	* Intravenous: 100% Intramuscular: 93%; Subcutaneous: high; Epidural: 77%; Intranasal: 8–50%; Sublingual: 24–30%; Rectal: 11–30%; By mouth: 16–29%;
Protein binding	12–47% (low)
Metabolism	Liver (N-demethylation): Major: CYP3A4; Minor: CYP2B6, CYP2C9;
Half-life	* Ketamine: 2.5–3 hours Norketamine: 12 hours;
Excretion	* Urine: 91% Feces: 1–3%;
Identifiers
CAS number	6740-88-1 1867-66-9 (hydrochloride); 33643-46-8 (esketamine); 33643-49-1 (arketamine);
ATC code	N01AX03
PubChem	CID 3821
IUPHAR ligand	4233
DrugBank	DB01221
ChemSpider	3689
UNII	690G0D6V8H
KEGG	D08098
ChEBI	CHEBI:6121
ChEMBL	CHEMBL742
Synonyms	CI-581; CL-369; CM-52372-2
Chemical data
Formula	C13H16ClNO
Mol. mass	237.725
	InChI InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3 ; Key:YQEZLKZALYSWHR-UHFFFAOYSA-N ;
Physical data
Melt. point	258–261 °C (496–502 °F)
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↑ 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]
↑ 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]
↑ ^3.0 ^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]
↑ Jianren Mao. (2016).
Opioid-Induced Hyperalgesia
CRC Press
↑ ^5.0 ^5.1 ^5.2 Pascal Kintz. (2014).
Toxicological Aspects of Drug-Facilitated Crimes
Elsevier Science
↑ 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]
↑ ^7.0 ^7.1 ^7.2 Sinner, B., & Graf, B.M. (2008).
Ketamine. Handbook of experimental pharmacology, (182), 313-33. [PubMed:18175098] [WorldCat] [DOI]
↑ 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]
↑ Alan F. Schatzberg & Charles B. Nemeroff. (2017).
The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition
American Psychiatric Pub, pp550-.
↑ ^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]
↑ Andrew Dickman & Jennifer Schneider. (2016).
The Syringe Driver: Continuous Subcutaneous Infusions in Palliative Care
Oxford University Press, pp. 114-
↑ Frank J. Dowd, Bart Johnson & Angelo Mariotti. (2016).
Pharmacology and Therapeutics for Dentistry – E-Book
Elsevier Health Sciences, pp235–
↑ 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]
↑ 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]
↑ I.K. Morton, & Judith M. Hall. (2012).
Concise Dictionary of Pharmacological Agents: Properties and Synonyms
Springer Science & Business Media, pp159–

[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]

[MathewZarate2016-3] 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]

[Mao2016-4] Jianren Mao. (2016).
Opioid-Induced Hyperalgesia
CRC Press

[Kintz2014-5] 5.0 ^5.1 ^5.2 Pascal Kintz. (2014).
Toxicological Aspects of Drug-Facilitated Crimes
Elsevier Science

[pmid29736744-6] 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]

[sinner-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]

[Hashimoto2019-8] 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]

[Nemeroff2017-9] Alan F. Schatzberg & Charles B. Nemeroff. (2017).
The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition
American Psychiatric Pub, pp550-.

[Zhang2018-10] 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]

[DickmanSchneider2016-11] Andrew Dickman & Jennifer Schneider. (2016).
The Syringe Driver: Continuous Subcutaneous Infusions in Palliative Care
Oxford University Press, pp. 114-

[DowdJohnson2016-12] 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]

[Quibell2011-14] 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]

[MortonHall2012-15] I.K. Morton, & Judith M. Hall. (2012).
Concise Dictionary of Pharmacological Agents: Properties and Synonyms
Springer Science & Business Media, pp159–

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