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| {{Drugbox|
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| | IUPAC_name = ''5-Ethyl-5-(1-methylbutyl)-<BR>2,4,6(1''H'',3''H'',5''H'')-pyrimidinetrione''
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| | image = Pentobarbital-2D-skeletal.png
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| | width = 247
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| | CAS_number = 76-74-4
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| | ATC_prefix = N05
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| | ATC_suffix = CA01
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| | ATC_supplemental =
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| | PubChem = 4737
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| | DrugBank = APRD01174
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| | C = 11 | H = 18 | N = 2 | O = 3
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| | molecular_weight = 226.1317
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| | bioavailability = 70-90% oral; 90% rectal
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| | protein_bound = 20-45%
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| | metabolism = [[Liver|Hepatic]]
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| | elimination_half-life = 15-48 hours
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| | excretion = [[Kidney|Renal]]
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| | pregnancy_category = D ([[United States|USA]])
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| | legal_status = [[United States|USA]]: [[Schedule II]] (oral and [[parenteral]]); [[Schedule III]] (rectal)
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| | routes_of_administration = Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for [[animal euthanasia]])
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| }}
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| '''Pentobarbital''' is a short acting [[barbiturate]] that is available as both a free acid and a sodium salt, the former of which is only slightly soluble in water and ethanol.<ref name=solubility>{{cite web | url = http://www.sdrl.com/druglist/pentobarbital.html | title = Pentobarbital | work = San Diego Reference Laboratory: Technical Help | accessdate = 16 July | accessyear = 2005 }}</ref> One trade name for this drug is '''Nembutal'''®, coined by Dr. John S. Lundy, who started using it in 1930, from the structural formula of the sodium salt—'''N'''a (sodium) + '''e'''thyl + '''m'''ethyl + '''but'''yl + '''al''' (common suffix for barbiturates).<ref name=Nembutal>{{cite journal | author=Lee C. Fosburgh | title=Imagining in Time: From this point in time: Some memories of my part in the history of anesthesia -- John S. Lundy, MD | journal=American Association of Nurse Anesthetists Journal | volume=65 | issue=4 | year=1997 | pages=323-8 | id = {{PMID|9281913}} | url = https://www.aana.com/archives/imagine/1997/08imagine97.asp}}</ref>
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| ==Uses==
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| ===Approved===
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| Pentobarbital's [[Food and Drug Administration|FDA]] approved human uses include treatment of [[seizure]]s
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| and preoperative (and other) [[sedation]]; it is also approved as a short-term [[hypnotic]].<ref name=approved_USA>{{cite book | last = Deglin | first = Judith Hopfer | coauthors = April Hazard Vallerand | title = Davis's Drug Guide for Nurses | origyear = 1988 | url = http://www.drugguide.com/monograph_library/additional_monographs/pentobarbital.htm | accessdate = 2005-07-16 | edition = 9th edition | date = 2004-06-01 | publisher = F. A. Davis Company | id = ISBN 978-0-8036-1154-2 | pages = 789}}</ref>
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| In France, it is used in the treatment of [[insomnia]], and as a preanesthetic.<ref name=approved_France>{{cite web | author = VIDAL | year = 2001 | title = PENTOBARBITAL SODIQUE | work = Banque de Données Automatisée sur les Médicaments | url = http://www.biam2.org/www/Sub2971.html | accessdate = May 2 | accessyear = 2006}}</ref>
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| ===Unapproved/Investigational/Off-Label===
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| Off-label uses of pentobarbital include reduction of intracranial pressure in [[Reye's syndrome]], traumatic brain injury<ref name=solubility /> and induction of coma in cerebral [[ischemia]] patients.<ref name=approved_USA />
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| ===Veterinary medicine===
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| In [[veterinary medicine]] sodium pentobarbital—traded under names such as ''Sagatal''—is used as an [[anaesthetic]].<ref name=veterinary_anesthesic>{{cite web | author=UBC Committee on Animal Care | year=2005 | title=Euthanasia | work=SOP 009E1 - euthanasia - overdose with pentobarbital | publisher=The University of British Columbia | url=http://www.acc.ubc.ca/SOP/SOPeuthp.html | accessdate=4 October | accessyear=2005}}</ref> Pentobarbital is an ingredient in [[Equithesin]].
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| ===Veterinary Euthanasia===
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| It is used by itself, or more often in combination with complementary agents such as [[phenytoin]], in commercial [[animal euthanasia]]<ref name=veterinary_euthanasia>{{cite web |author=Unknown | year=2003 | title=ANESTHESIA AND ANALGESIA | work=Animal Use Protocols | publisher=University of Virginia | url=http://www.healthsystem.virginia.edu/internet/ccm/Anesth/aneshome.cfm | accessdate=4 October | accessyear=2005}}</ref> injectable solutions. Trade names include ''Euthasol'', ''Euthatal'', ''Beuthanasia-D'' and ''Fatal Plus''.
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| ===Human Euthanasia===
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| Pentobarbital has also been used for physician-assisted suicide. Pentobarbital was used for this purpose in the Northern Territory of Australia, prior to euthanasia becoming illegal. It is also commonly used in Oregon for physician assisted suicide. <ref name=human_euthanasia>{{cite web|url=http://www.cnsnews.com/Culture/Archive/200203/CUL20020326a.html |title=Campaigners Rally Round Right-To-Die Woman |accessmonthday=July 22 |accessyear=2006 |last=Goodenough |first=Patrick |date=2002-03-26 |work=CNSNews.com}}</ref>
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| ==Folklore==
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| A pentobarbital suppository was cited in an October 2006 [http://wnd.com/news/article.asp?ARTICLE_ID=52493 news article] in [http://wnd.com/ WorldNetDaily.com] as the cause of death of Marilyn Monroe.
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| The Beatles were accusedfact|date=July 2007 of writing their 1966 hit Yellow Submarine while under the [[psychoactive]] effects of Nembutal, though band members denied the allegations.
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| The Clash makes a reference to it in the song The Right Profile from the album London Calling in which the lyrics read "Nembutal numbs it all, But I prefer… alcohol!".
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| ==Metabolism==
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| [[Image:pentobarbital DOJ.jpg|frame|left]]
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| Pentobarbital undergoes [[metabolism|first-pass metabolism]] in the liver and possibly the intestines.<ref name=first-pass>{{cite journal | first = R. G. | last = Knodell | coauthors = Spector MH, Brooks DA, Keller FX, Kyner WT. | month = December | year = 1980 | title = Alterations in pentobarbital pharmacokinetics in response to parenteral and enteral alimentation in the rat | journal = Gastroenterology | volume = 79 | issue = 6 | pages = 1211-6 | pmid = 6777235}}</ref>
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| ==Drug Interactions==
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| Administration of [[alcohol]], [[opioid]]s, [[antihistamine]]s, other [[sedative|sedative-hypnotic]]s, and other [[central nervous system]] depressants will additively increase the sedation caused by pentobarbital.<ref name=approved_USA />
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| <!--
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| The S-[[isomer]]s of [[fluoxetine]] and its active [[metabolite]], norfluoxetine, reverse the [[down-regulation]] of [[allopregnanolone]] by pentobarbital, thus reversing the loss of [[righting reflex]], at doses 10-50 times lower than that required for serotonin reuptake.<ref name=not_with_fluoxetine>{{cite journal | first = Graziano | last = Pinna | coauthors = Erminio Costa and Alessandro Guidotti | date = April 20, 2004 | title = Fluoxetine and norfluoxetine stereospecifically facilitate pentobarbital sedation by increasing neurosteroids | journal = Proceedings of the National Academy of the United States of America | volume = 101 | issue = 16 | pages = 6222-6225 | id = {{doi|10.1073/pnas.0401479101}}| url = http://www.pnas.org/cgi/content/full/101/16/6222}}</ref>
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| [[Tricyclic antidepressant]]s decrease serum levels of pentobarbital.
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| ==References and End Notes==
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| <div class="references-small">{{reflist|2}}</div>
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| ==External links==
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| {{Barbiturates}}
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| [[Category:Anticonvulsants]]
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| [[Category:barbiturates]]
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| [[de:Pentobarbital]]
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| [[ja:ペントバルビタール]]
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| [[pt:Pentobarbital]]
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| [[ru:Этаминал-натрий]]
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| [[sv:Pentobarbital]]
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| [[fi:Pentobarbitaali]]
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| {{WikiDoc Sources}}
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