「ケタミン」の版間の差分

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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" /><ref name="MD" />
+
| 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>
 
| addiction_liability = Low–moderate<ref name="NHM-PCP and ketamine">{{cite book |vauthors=Malenka RC, Nestler EJ, Hyman SE |veditors=Sydor A, Brown RY |title=Molecular Neuropharmacology: A Foundation for Clinical Neuroscience |year=2009 |publisher=McGraw-Hill Medical |location=New York |isbn=978-0-07-148127-4 | pages=374–375 |edition=2nd |chapter=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}}</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">{{cite book |vauthors=Malenka RC, Nestler EJ, Hyman SE |veditors=Sydor A, Brown RY |title=Molecular Neuropharmacology: A Foundation for Clinical Neuroscience |year=2009 |publisher=McGraw-Hill Medical |location=New York |isbn=978-0-07-148127-4 | pages=374–375 |edition=2nd |chapter=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}}</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
34行目: 34行目:
 
* [[Subcutaneous injection|Subcutaneous]]: high<ref name="Mao2016">{{cite book |author=Jianren Mao |title=Opioid-Induced Hyperalgesia |url=https://books.google.com/books?id=_VrvBQAAQBAJ&pg=PA127 |date=19 April 2016 |publisher=CRC Press |isbn=978-1-4200-8900-4 |pages=127– |url-status=live |archiveurl=https://web.archive.org/web/20170908185726/https://books.google.com/books?id=_VrvBQAAQBAJ&pg=PA127 |archivedate=8 September 2017 }}</ref>
 
* [[Subcutaneous injection|Subcutaneous]]: high<ref name="Mao2016">{{cite book |author=Jianren Mao |title=Opioid-Induced Hyperalgesia |url=https://books.google.com/books?id=_VrvBQAAQBAJ&pg=PA127 |date=19 April 2016 |publisher=CRC Press |isbn=978-1-4200-8900-4 |pages=127– |url-status=live |archiveurl=https://web.archive.org/web/20170908185726/https://books.google.com/books?id=_VrvBQAAQBAJ&pg=PA127 |archivedate=8 September 2017 }}</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">{{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>
* [[Intranasal administration|Intranasal]]: 8–50%<ref name="MathewZarate2016" /><ref name="pmid29736744"> 29736744</ref><ref name="sinner" />
+
* [[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 />
+
* [[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>
 
* [[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 />
 
* [[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 />
| protein_bound = 12–47% (low)<ref name="Kintz2014" /><ref name="sinner" /><ref name="DowdJohnson2016" />
+
| 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>
 
| 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]]
49行目: 49行目:
 
| onset =
 
| onset =
 
* Intravenous: seconds<ref name="sinner" />
 
* Intravenous: seconds<ref name="sinner" />
* Intramuscular: 1–5 min<ref name="sinner" /><ref name="Quibell2011" />
+
* Intramuscular: 1–5 min<ref name="sinner" /><ref name="Quibell2011"><pubmed>21419322</pubmed></ref>
 
* Subcutaneous: 15–30 min<ref name="Quibell2011" />
 
* Subcutaneous: 15–30 min<ref name="Quibell2011" />
 
* Insufflation: 5–10 min<ref name="sinner" />
 
* Insufflation: 5–10 min<ref name="sinner" />
87行目: 87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" />
+
| 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>
  
 
<!--Chemical data-->
 
<!--Chemical data-->

2020年7月9日 (木) 15:50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]
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. Brayfield, A, ed. (9 January 2017). "Ketamine Hydrochloride: Martindale: The Complete Drug Reference". MedicinesComplete. London, UK: Pharmaceutical Press. Retrieved 24 August 2017.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  5. Jianren Mao (19 April 2016). Opioid-Induced Hyperalgesia. CRC Press. pp. 127–. ISBN 978-1-4200-8900-4. Archived from the original on 8 September 2017.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  6. 6.0 6.1 6.2 Pascal Kintz (22 March 2014). Toxicological Aspects of Drug-Facilitated Crimes. Elsevier Science. pp. 87–. ISBN 978-0-12-416969-2. Archived from the original on 8 September 2017.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  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. pp. 550–. ISBN 978-1-58562-523-9. Archived from the original on 8 September 2017.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  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 (22 September 2016). The Syringe Driver: Continuous Subcutaneous Infusions in Palliative Care. Oxford University Press. pp. 114–. ISBN 978-0-19-873372-0. Archived from the original on 8 September 2017.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  13. Frank J. Dowd; Bart Johnson; Angelo Mariotti (3 September 2016). Pharmacology and Therapeutics for Dentistry – E-Book. Elsevier Health Sciences. pp. 235–. ISBN 978-0-323-44595-5.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  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. 引用エラー: 無効な <ref> タグです。 「Quibell2011」という名前の引用句に対するテキストが指定されていません
  16. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 159–. ISBN 978-94-011-4439-1. Archived from the original on 11 April 2017.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>