「ケタミン」の版間の差分

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15行目: 15行目:
 
| licence_US = Ketamine
 
| licence_US = Ketamine
 
| pregnancy_AU = B3
 
| pregnancy_AU = B3
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Ketamine (Ketalar) Use During Pregnancy | website=Drugs.com | date=22 November 2019 | url=https://www.drugs.com/pregnancy/ketamine.html | access-date=18 May 2020}}</ref>
+
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">https://www.drugs.com/pregnancy/ketamine.html</ref>
 
| pregnancy_US = N
 
| pregnancy_US = N
 
| pregnancy_US_comment = <ref name="Drugs.com pregnancy" />
 
| pregnancy_US_comment = <ref name="Drugs.com pregnancy" />
24行目: 24行目:
 
| legal_US = Schedule III
 
| legal_US = Schedule III
 
| legal_UN = Unscheduled
 
| legal_UN = Unscheduled
| routes_of_administration = Any<ref><pubmed>28657160</pubmed></ref><ref><pubmed> 28339431 </pubmed></ref><ref name="MathewZarate2016"><pubmed>24257811 </pubmed></ref><ref name="MD">{{cite web|title=Ketamine Hydrochloride: Martindale: The Complete Drug Reference|date=9 January 2017|accessdate=24 August 2017|editor=Brayfield, A|publisher=Pharmaceutical Press|website=MedicinesComplete|url=https://www.medicinescomplete.com/mc/martindale/current/ms-3114-h.htm|location=London, UK}}</ref>
+
| routes_of_administration = Any<ref><pubmed>28657160</pubmed></ref><ref><pubmed> 28339431 </pubmed></ref><ref name="MathewZarate2016"><pubmed>24257811 </pubmed></ref><ref name="MD">[https://www.medicinescomplete.com/mc/martindale/current/ms-3114-h.htm Medicines Complete]</ref>
 
| addiction_liability = Low–moderate<ref name="NHM-PCP and ketamine">'''Malenka RC, Nestler EJ, Hyman SE'''<br>Chapter 15: Reinforcement and Addictive Disorders |quote=Phencyclidine (PCP or angel dust) and ketamine (also known as special K) are structurally related drugs... their reinforcing properties and risks related to compulsive abuse<br>edited by Sydor A, Brown RY, Molecular Neuropharmacology: A Foundation for Clinical Neuroscience 2nd ed. pp. 374–375 (2009) McGraw-Hill Medical, New York</ref><!--Start widen drugbox--><br />&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<!--End widen drugbox-->
 
| addiction_liability = Low–moderate<ref name="NHM-PCP and ketamine">'''Malenka RC, Nestler EJ, Hyman SE'''<br>Chapter 15: Reinforcement and Addictive Disorders |quote=Phencyclidine (PCP or angel dust) and ketamine (also known as special K) are structurally related drugs... their reinforcing properties and risks related to compulsive abuse<br>edited by Sydor A, Brown RY, Molecular Neuropharmacology: A Foundation for Clinical Neuroscience 2nd ed. pp. 374–375 (2009) McGraw-Hill Medical, New York</ref><!--Start widen drugbox--><br />&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;<!--End widen drugbox-->
 
| class = [[NMDA receptor antagonists]]; [[General anesthetics]]; [[Dissociative hallucinogen]]s; [[Analgesic]]s; [[Antidepressant]]s
 
| class = [[NMDA receptor antagonists]]; [[General anesthetics]]; [[Dissociative hallucinogen]]s; [[Analgesic]]s; [[Antidepressant]]s
33行目: 33行目:
 
* [[Intramuscular injection|Intramuscular]]: 93%<ref name="MathewZarate2016" />
 
* [[Intramuscular injection|Intramuscular]]: 93%<ref name="MathewZarate2016" />
 
* [[Subcutaneous injection|Subcutaneous]]: high<ref name="Mao2016">'''Jianren Mao'''<br>Opioid-Induced Hyperalgesia <br>CRC Press, April 2016</ref>
 
* [[Subcutaneous injection|Subcutaneous]]: high<ref name="Mao2016">'''Jianren Mao'''<br>Opioid-Induced Hyperalgesia <br>CRC Press, April 2016</ref>
* [[Epidural administration|Epidural]]: 77%<ref name="Kintz2014">{{cite book |author=Pascal Kintz |title=Toxicological Aspects of Drug-Facilitated Crimes |url=https://books.google.com/books?id=YgnUAgAAQBAJ&pg=PA87 |date=22 March 2014 |publisher=Elsevier Science |isbn=978-0-12-416969-2 |pages=87– |url-status=live |archiveurl=https://web.archive.org/web/20170908185726/https://books.google.com/books?id=YgnUAgAAQBAJ&pg=PA87 |archivedate=8 September 2017 }}</ref>
+
* [[Epidural administration|Epidural]]: 77%<ref name="Kintz2014">'''Pascal Kintz. (2014).'''<br>Toxicological Aspects of Drug-Facilitated Crimes<br>Elsevier Science</ref>
 
* [[Intranasal administration|Intranasal]]: 8–50%<ref name="MathewZarate2016" /><ref name="pmid29736744"><pubmed> 29736744</pubmed></ref><ref name="sinner"><pubmed> 18175098 </pubmed></ref>
 
* [[Intranasal administration|Intranasal]]: 8–50%<ref name="MathewZarate2016" /><ref name="pmid29736744"><pubmed> 29736744</pubmed></ref><ref name="sinner"><pubmed> 18175098 </pubmed></ref>
 
* [[Sublingual administration|Sublingual]]: 24–30%<ref name="MathewZarate2016" /><ref name="Hashimoto2019"><pubmed>31215725</pubmed></ref>
 
* [[Sublingual administration|Sublingual]]: 24–30%<ref name="MathewZarate2016" /><ref name="Hashimoto2019"><pubmed>31215725</pubmed></ref>
* [[Rectal administration|Rectal]]: 11–30%<ref name="Nemeroff2017">{{cite book |author1=Alan F. Schatzberg |author2=Charles B. Nemeroff |title=The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition |url=https://books.google.com/books?id=KfHEDgAAQBAJ&pg=PA550 |year=2017 |publisher=American Psychiatric Pub |isbn=978-1-58562-523-9 |pages=550– |url-status=live |archiveurl=https://web.archive.org/web/20170908185726/https://books.google.com/books?id=KfHEDgAAQBAJ&pg=PA550 |archivedate=8 September 2017 }}</ref><ref name=Zhang2018><pubmed> 30513009</pubmed> </ref>
+
* [[Rectal administration|Rectal]]: 11–30%<ref name="Nemeroff2017">
* [[Oral administration|By mouth]]: 16–29%<ref name="Kintz2014" /><ref name="DickmanSchneider2016">{{cite book |author1=Andrew Dickman |author2=Jennifer Schneider |title=The Syringe Driver: Continuous Subcutaneous Infusions in Palliative Care |url=https://books.google.com/books?id=jbUSDQAAQBAJ&pg=PA114 |date=22 September 2016 |publisher=[[Oxford University Press]] |isbn=978-0-19-873372-0 |pages=114– |url-status=live |archiveurl=https://web.archive.org/web/20170908185726/https://books.google.com/books?id=jbUSDQAAQBAJ&pg=PA114 |archivedate=8 September 2017 }}</ref><ref name=Zhang2018 />
+
'''Alan F. Schatzberg, Charles B. Nemeroff. (2017)'''<br>The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition<br>American Psychiatric Pub, pp550-.</ref>
| protein_bound = 12–47% (low)<ref name="Kintz2014" /><ref name="sinner" /><ref name="DowdJohnson2016">{{cite book|author1=Frank J. Dowd|author2=Bart Johnson|author3=Angelo Mariotti|title=Pharmacology and Therapeutics for Dentistry – E-Book|url=https://books.google.com/books?id=6xT7DAAAQBAJ&pg=PA235|date=3 September 2016|publisher=Elsevier Health Sciences|isbn=978-0-323-44595-5|pages=235–}}</ref>
+
<ref name=Zhang2018><pubmed> 30513009</pubmed> </ref>
 +
* [[Oral administration|By mouth]]: 16–29%<ref name="Kintz2014" /><ref name="DickmanSchneider2016">'''Andrew Dickman, Jennifer Schneider. (2016)'''<br>The Syringe Driver: Continuous Subcutaneous Infusions in Palliative Care<br>Oxford University Press, pp. 114-</ref><ref name=Zhang2018 />
 +
| protein_bound = 12–47% (low)<ref name="Kintz2014" /><ref name="sinner" /><ref name="DowdJohnson2016">'''Frank J. Dowd, Bart Johnson, Angelo Mariotti. (2016)'''<br>Pharmacology and Therapeutics for Dentistry – E-Book<br>Elsevier Health Sciences, pp235–</ref>
 
| metabolism = [[Liver]] ([[demethylation|''N''-demethylation]]):<ref name="MathewZarate2016" /><ref><pubmed>12065445</pubmed></ref>
 
| metabolism = [[Liver]] ([[demethylation|''N''-demethylation]]):<ref name="MathewZarate2016" /><ref><pubmed>12065445</pubmed></ref>
 
* Major: [[CYP3A4]]
 
* Major: [[CYP3A4]]
87行目: 89行目:
 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
 
| ChEMBL = 742
 
| ChEMBL = 742
| synonyms = CI-581; CL-369; CM-52372-2<ref name="MortonHall2012">{{cite book |author1=I.K. Morton |author2=Judith M. Hall |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA159 |date=6 December 2012 |publisher=Springer Science & Business Media |isbn=978-94-011-4439-1 |pages=159– |url-status=live |archiveurl=https://web.archive.org/web/20170411144623/https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA159 |archivedate=11 April 2017 }}</ref>
+
| synonyms = CI-581; CL-369; CM-52372-2<ref name="MortonHall2012">'''I. K. Morton, Judith M. Hall. (2012)'''<br>Concise Dictionary of Pharmacological Agents: Properties and Synonyms<br>Springer Science & Business Media, pp159–</ref>
  
 
<!--Chemical data-->
 
<!--Chemical data-->

2020年7月9日 (木) 22:29時点における版

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][4]
Pharmacokinetic data
Bioavailability * Intravenous: 100%[3]

[11]

Protein binding 12–47% (low)[6][8][13]
Metabolism Liver (N-demethylation):[3][14]
Half-life * Ketamine: 2.5–3 hours[8][3]
  • Norketamine: 12 hours[15]
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[16]
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. Medicines Complete
  5. Jianren Mao
    Opioid-Induced Hyperalgesia
    CRC Press, April 2016
  6. 6.0 6.1 6.2 Pascal Kintz. (2014).
    Toxicological Aspects of Drug-Facilitated Crimes
    Elsevier Science
  7. 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]
  8. 8.0 8.1 8.2 Sinner, B., & Graf, B.M. (2008).
    Ketamine. Handbook of experimental pharmacology, (182), 313-33. [PubMed:18175098] [WorldCat] [DOI]
  9. 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]
  10. Alan F. Schatzberg, Charles B. Nemeroff. (2017)
    The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition
    American Psychiatric Pub, pp550-.
  11. 11.0 11.1 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]
  12. Andrew Dickman, Jennifer Schneider. (2016)
    The Syringe Driver: Continuous Subcutaneous Infusions in Palliative Care
    Oxford University Press, pp. 114-
  13. Frank J. Dowd, Bart Johnson, Angelo Mariotti. (2016)
    Pharmacology and Therapeutics for Dentistry – E-Book
    Elsevier Health Sciences, pp235–
  14. 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]
  15. 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]
  16. I. K. Morton, Judith M. Hall. (2012)
    Concise Dictionary of Pharmacological Agents: Properties and Synonyms
    Springer Science & Business Media, pp159–