Pentobarbital
2246554
223756358
2008-07-05T17:14:39Z
CielProfond
1520890
/* Veterinary Euthanasia */ Added Euthanyl
{{Drugbox|
| IUPAC_name = ''5-Ethyl-5-(1-methylbutyl)-<BR>2,4,6(1''H'',3''H'',5''H'')-pyrimidinetrione''
| image = Pentobarbital-2D-skeletal.png
| width = 247
| CAS_number = 76-74-4
| ATC_prefix = N05
| ATC_suffix = CA01
| ATC_supplemental =
| PubChem = 4737
| DrugBank = APRD01174
| C = 11 | H = 18 | N = 2 | O = 3
| molecular_weight = 226.1317
| bioavailability = 70-90% oral; 90% rectal
| protein_bound = 20-45%
| metabolism = [[Liver|Hepatic]]
| elimination_half-life = 15-48 hours
| excretion = [[Kidney|Renal]]
| pregnancy_category = D ([[United States|USA]])
| legal_status = [[United States|USA]]: [[Schedule II]] (oral and [[parenteral]]); [[Schedule III]] (rectal)
| routes_of_administration = Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for [[animal euthanasia]])
}}
'''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 | accessdaymonth = 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 | pmid = 9281913 | url = https://www.aana.com/archives/imagine/1997/08imagine97.asp | format={{Dead link|date=May 2008}}}}</ref>
==Uses==
===Approved===
Pentobarbital's [[Food and Drug Administration|FDA]] approved human uses include treatment of [[seizure]]s
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>
In France and the Netherlands, it is no longer used in the treatment of [[insomnia]], nor 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 | accessmonthday = May 2 | accessyear = 2006}}</ref>
===Unapproved/Investigational/Off-Label===
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 />
===Veterinary Medicine===
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 | accessdaymonth=4 October | accessyear=2005}}</ref> Pentobarbital is an ingredient in [[Equithesin]].
===Veterinary Euthanasia===
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 | accessdaymonth=4 October | accessyear=2005}}</ref> injectable solutions. Trade names include ''Euthasol'', ''Euthatal'', ''Euthanyl'' (in Canada), ''Beuthanasia-D'', and ''Fatal Plus''.
===Human Euthanasia===
In the [[Netherlands]], a pentobarbital elixer is used as an alternative for patients who wish to take the barbiturate needed for the lethal cocktail themselves, instead of having it administered intravenously, in which case [[thiopenthal]] is used. Pentobarbital has no medical use anymore in the Netherlands, and is only used for euthanasia.
Pentobarbital has also been used for physician-assisted suicide. It is 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>, and is also used by [[Dignitas (euthanasia group)]]. Pentobarbital was also used for this purpose in the Northern Territory of Australia, prior to euthanasia becoming illegal in that region.
==Folklore==
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]].
[[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!"
The song "[[Yellow Submarine (song)|Yellow Submarine]]" by [[The Beatles]] is rumored to reference to Nembutal due to the color and shape of the capsules. However, [[Paul McCartney]] has denied this, stating that he had written the song as a children's tune.
==Metabolism==
[[Image:pentobarbital DOJ.jpg|frame|right]]
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>
==Drug Interactions==
Administration of [[alcohol]], [[opioid]]s, [[antihistamine]]s, other [[sedative|sedative-hypnotic]]s, and other [[central nervous system]] depressants will greatly increase the sedation caused by pentobarbital.<ref name=approved_USA />
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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 | doi = 10.1073/pnas.0401479101| url = http://www.pnas.org/cgi/content/full/101/16/6222 | pmid = 15069199}}</ref>
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==References and End Notes==
{{reflist}}
==External links==
{{Barbiturates}}
{{Anticonvulsants}}
{{Hypnotics and sedatives}}
[[Category:Anticonvulsants]]
[[Category:barbiturates]]
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