「ケタミン」の版間の差分

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(ページの作成:「{{Drugbox | Watchedfields = changed | verifiedrevid = 477168837 | IUPAC_name = (''RS'')-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone | image = Ketamine2DCSD.svg | widt…」)
 
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>{{cite journal |last1=Bell |first1=RF |last2=Eccleston |first2=C |last3=Kalso |first3=EA |title=Ketamine as an adjuvant to opioids for cancer pain |journal=[[Cochrane Database of Systematic Reviews]] |date=28 June 2017 |volume=6 |pages=CD003351 |doi=10.1002/14651858.CD003351.pub3 |pmid=28657160 |pmc=6481583 |url=http://opus.bath.ac.uk/57535/1/Published_Version.pdf}}</ref><ref>{{cite journal |last1=Moyse |first1=DW |last2=Kaye |first2=AD |last3=Diaz |first3=JH |last4=Qadri |first4=MY |last5=Lindsay |first5=D |last6=Pyati |first6=S |title=Perioperative Ketamine Administration for Thoracotomy Pain |journal=Pain Physician |date=March 2017 |volume=20 |issue=3 |pages=173–184 |pmid=28339431}}</ref><ref name="MathewZarate2016" /><ref name="MD" />
+
| routes_of_administration = Any<ref><pubmed>28657160</pubmed></ref><ref><pubmed> 28339431 </pubmed></ref><ref name="MathewZarate2016" /><ref name="MD" />
 
| 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">{{cite journal |vauthors=Molero P, Ramos-Quiroga JA, Martin-Santos R, Calvo-Sánchez E, Gutiérrez-Rojas L, Meana JJ |title=Antidepressant Efficacy and Tolerability of Ketamine and Esketamine: A Critical Review |journal=CNS Drugs |volume=32 |issue=5 |pages=411–420 |date=May 2018 |pmid=29736744 |doi=10.1007/s40263-018-0519-3 |url= }}</ref><ref name="sinner" />
+
* [[Intranasal administration|Intranasal]]: 8–50%<ref name="MathewZarate2016" /><ref name="pmid29736744"> 29736744</ref><ref name="sinner" />
* [[Sublingual administration|Sublingual]]: 24–30%<ref name="MathewZarate2016" /><ref name="Hashimoto2019">{{cite journal|last1=Hashimoto|first1=Kenji|title=Rapid‐acting antidepressant ketamine, its metabolites and other candidates: A historical overview and future perspective|journal=Psychiatry and Clinical Neurosciences|volume=73|issue=10|year=2019|pages=613–627|issn=1323-1316|doi=10.1111/pcn.12902|pmid=31215725|pmc=6851782}}</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 />
 
* [[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" />
| metabolism = [[Liver]] ([[demethylation|''N''-demethylation]]):<ref name="MathewZarate2016" /><ref>{{cite journal |last1=Hijazi |first1=Y |last2=Boulieu |first2=R |title=Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes |journal=[[Drug Metabolism and Disposition]] |volume=30 |issue=7 |pages=853–8 |date=July 2002 |pmid=12065445 |doi=10.1124/dmd.30.7.853|url=https://semanticscholar.org/paper/935c35b819e091b777788d99379fbb33bcc9e24f }}</ref>
+
| metabolism = [[Liver]] ([[demethylation|''N''-demethylation]]):<ref name="MathewZarate2016" /><ref><pubmed>12065445</pubmed></ref>
 
* Major: [[CYP3A4]]
 
* Major: [[CYP3A4]]
 
* Minor: [[CYP2B6]], [[CYP2C9]]
 
* Minor: [[CYP2B6]], [[CYP2C9]]

2020年7月9日 (木) 15:23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 引用エラー: 無効な <ref> タグです。 「MathewZarate2016」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
  4. 引用エラー: 無効な <ref> タグです。 「MD」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
  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. 29736744
  8. 8.0 8.1 8.2 引用エラー: 無効な <ref> タグです。 「sinner」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
  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 引用エラー: 無効な <ref> タグです。 「Zhang2018」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
  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. 引用エラー: 無効な <ref> タグです。 「DowdJohnson2016」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
  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. 引用エラー: 無効な <ref> タグです。 「MortonHall2012」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