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{{box|text= アリルシクロヘキシルアミン系の解離性麻酔薬であり、世界保健機関による必須医薬品の一つである。薬物乱用が問題になり麻薬指定された。精神医学領域では、ケタミンは統合失調症モデルとして使用されているが、近年、ケタミンの即効性抗うつ効果が注目されている。}} | {{box|text= アリルシクロヘキシルアミン系の解離性麻酔薬であり、世界保健機関による必須医薬品の一つである。薬物乱用が問題になり麻薬指定された。精神医学領域では、ケタミンは統合失調症モデルとして使用されているが、近年、ケタミンの即効性抗うつ効果が注目されている。}} | ||
{{Drugbox | |||
| Watchedfields = changed | |||
| verifiedrevid = 477168837 | |||
| IUPAC_name = (''RS'')-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone | |||
| image = Ketamine2DCSD.svg | |||
| width = 150px | |||
| image2 = S-ketamine-from-HCl-xtal-3D-balls.png | |||
| width2 = 175px | |||
| alt2 = (''S'')-Ketamine ball-and-stick model | |||
<!--Clinical data--> | |||
| tradename = Ketalar, others | |||
| Drugs.com = {{drugs.com|monograph|ketamine-hydrochloride}} | |||
| DailyMedID = Ketamine | |||
| licence_US = Ketamine | |||
| pregnancy_AU = B3 | |||
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">https://www.drugs.com/pregnancy/ketamine.html</ref> | |||
| pregnancy_US = N | |||
| pregnancy_US_comment = <ref name="Drugs.com pregnancy" /> | |||
| legal_status = Rx-only | |||
| legal_AU = S8 | |||
| legal_CA = Schedule I | |||
| legal_UK = Class B | |||
| legal_US = Schedule III | |||
| legal_UN = Unscheduled | |||
| routes_of_administration = Any<ref><pubmed>28657160</pubmed></ref><ref><pubmed> 28339431 </pubmed></ref><ref name="MathewZarate2016"><pubmed>24257811 </pubmed></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 /> <!--End widen drugbox--> | |||
| class = [[NMDA receptor antagonists]]; [[General anesthetics]]; [[Dissociative hallucinogen]]s; [[Analgesic]]s; [[Antidepressant]]s | |||
<!--Pharmacokinetic data--> | |||
| bioavailability = | |||
* [[Intravenous therapy|Intravenous]]: 100%<ref name="MathewZarate2016" /> | |||
* [[Intramuscular injection|Intramuscular]]: 93%<ref name="MathewZarate2016" /> | |||
* [[Subcutaneous injection|Subcutaneous]]: high<ref name="Mao2016">'''Jianren Mao. (2016).'''<br>Opioid-Induced Hyperalgesia <br>CRC Press</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> | |||
* [[Sublingual administration|Sublingual]]: 24–30%<ref name="MathewZarate2016" /><ref name="Hashimoto2019"><pubmed>31215725</pubmed></ref> | |||
* [[Rectal administration|Rectal]]: 11–30%<ref name="Nemeroff2017"> | |||
'''Alan F. Schatzberg & Charles B. Nemeroff. (2017).'''<br>The American Psychiatric Association Publishing Textbook of Psychopharmacology, Fifth Edition<br>American Psychiatric Pub, pp550-.</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> | |||
* Major: [[CYP3A4]] | |||
* Minor: [[CYP2B6]], [[CYP2C9]] | |||
| metabolites = | |||
* [[Norketamine]] | |||
* [[Dehydronorketamine]] | |||
* [[Hydroxynorketamine]] | |||
* [[Conjugation (biochemistry)|Conjugates]]<ref name="Levine2003">{{cite book |author=Barry Levine |title=Principles of Forensic Toxicology |url=https://books.google.com/books?id=k7BInEQ-iqgC&pg=PA282 |year=2003 |publisher=[[American Association for Clinical Chemistry]] |isbn=978-1-890883-87-4 |pages=282– |url-status=live |archiveurl=https://web.archive.org/web/20170908185726/https://books.google.com/books?id=k7BInEQ-iqgC&pg=PA282 |archivedate=8 September 2017 }}</ref> | |||
| onset = | |||
* Intravenous: seconds<ref name="sinner" /> | |||
* Intramuscular: 1–5 min<ref name="sinner" /><ref name="Quibell2011">{{cite journal |last1= Quibell |first1= R |last2= Prommer |first2= EE |last3= Mihalyo |first3= M |last4= Twycross |first4= R |last5= Wilcock |first5= A |displayauthors= 4 |title= Ketamine* |journal= [[Journal of Pain and Symptom Management]] |date= March 2011 |volume= 41 |issue= 3 |pages= 640–9 |doi= 10.1016/j.jpainsymman.2011.01.001 |pmid= 21419322 |url= http://www.jpsmjournal.com/article/S0885-3924%2811%2900046-7/fulltext |type= Therapeutic Review|doi-access= free }}</ref> | |||
* Subcutaneous: 15–30 min<ref name="Quibell2011" /> | |||
* Insufflation: 5–10 min<ref name="sinner" /> | |||
* By mouth: 15–30 min<ref name="sinner" /><ref name="Quibell2011" /> | |||
| elimination_half-life = | |||
* Ketamine: 2.5–3 hours<ref name="sinner" /><ref name="MathewZarate2016" /> | |||
* Norketamine: 12 hours<ref name="Quibell2011" ><pubmed> 21419322</pubmed></ref> | |||
| duration_of_action = | |||
* Intramuscular: 0.5–2 hours<ref name="Quibell2011" /> | |||
* Insufflation: 45–60 min<ref name="sinner" /> | |||
* By mouth: 1–6+ hours<ref name="sinner" /><ref name="Quibell2011" /> | |||
| excretion = | |||
* [[Urine]]: 91%<ref name="MathewZarate2016" /> | |||
* [[Feces]]: 1–3%<ref name="MathewZarate2016" /> | |||
<!--Identifiers--> | |||
| IUPHAR_ligand = 4233 | |||
| CAS_number_Ref = {{cascite|correct|??}} | |||
| CAS_number = 6740-88-1 | |||
| CAS_supplemental = {{plainlist| | |||
* 1867-66-9 ([[hydrochloride]]) | |||
* 33643-46-8 ([[esketamine]]) | |||
* 33643-49-1 ([[arketamine]])}} | |||
| ATC_prefix = N01 | |||
| ATC_suffix = AX03 | |||
| ChEBI_Ref = {{ebicite|correct|EBI}} | |||
| ChEBI = 6121 | |||
| PubChem = 3821 | |||
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | |||
| DrugBank = DB01221 | |||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
| ChemSpiderID = 3689 | |||
| UNII_Ref = {{fdacite|correct|FDA}} | |||
| UNII = 690G0D6V8H | |||
| KEGG_Ref = {{keggcite|correct|kegg}} | |||
| KEGG = D08098 | |||
| ChEMBL_Ref = {{ebicite|correct|EBI}} | |||
| ChEMBL = 742 | |||
| 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--> | |||
| C=13 | H=16 | Cl=1 | N=1 | O=1 | |||
| molecular_weight = 237.725 | |||
| chirality = [[Racemic mixture]]:<ref name="sinner" /> | |||
* [[Esketamine]] (''S''(+)-isomer) | |||
* [[Arketamine]] (''R''(−)-isomer) | |||
| SMILES = Clc1ccccc1C2(NC)CCCCC2=O | |||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChI = 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 | |||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChIKey = YQEZLKZALYSWHR-UHFFFAOYSA-N | |||
<!--Physical data--> | |||
| melting_point = 258 | |||
| melting_high = 261 | |||
<!--Empty--> | |||
| alt=|caption=|type=|MedlinePlus=|licence_EU=|pregnancy_category= | |||
}} | |||
== 歴史 == | == 歴史 == | ||