Pentobarbital
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AHFS/Drugs.com | Monograph |
MedlinePlus | a682416 |
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Routes of administration | Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for animal euthanasia) |
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Pharmacokinetic data | |
Bioavailability | 70-90% oral; 90% rectal |
Protein binding | 20-45% |
Metabolism | Hepatic |
Elimination half-life | 15-48 hours |
Excretion | Renal |
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ECHA InfoCard | 100.000.895 |
Chemical and physical data | |
Formula | C11H18N2O3 |
Molar mass | 226.27 g·mol−1 |
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Pentobarbital is a short-acting barbiturate that was first synthesized in 1928. Pentobarbital is available as both a free acid and a sodium salt, the former of which is only slightly soluble in water and ethanol.[1] One brand 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—Na (sodium) + ethyl + methyl + butyl + al (common suffix for barbiturates).[2]
Uses
Approved
Pentobarbital's FDA-approved human uses include treatment of seizures and preoperative (and other) sedation; it is also approved as a short-term hypnotic.[3]
Unapproved / investigational / off-label
Off-label uses of pentobarbital include reduction of intracranial pressure in Reye's syndrome, traumatic brain injury and induction of coma in cerebral ischemia patients.[3] Pentobarbital-induced coma has been advocated in patients with acute liver failure refractory to mannitol.[4]
Veterinary medicine
In veterinary medicine, sodium pentobarbital is used as an anaesthetic. It is also used by itself, or in combination with complementary agents such as phenytoin, in commercial animal euthanasia injectable solutions. [5]
Human euthanasia
In the Netherlands, the standard protocol for Physician-assisted euthanesia is intravenously induced Thiopental anesthesia, followed by Alcuronium bromide or Pancuronium bromide induced respiratory collapse. If the patient wishes to take the euthanasiant him/herself, the standard protocol is a concentrated oral solution of 100ml mixtura nontherapeutica pentobarbitali containing 9 grams of Pentobarbital sodium along with sugar syrup in a 20% Ethanol solution.[6] (Dutch)
Pentobarbital has also been used for physician-assisted suicide. In the US state of Oregon, "oral doses of a barbiturate" have been used for this purpose.[7]
In Switzerland, the only country that allows foreigners to have assisted suicide, the Dignitas clinic uses the antiemetic drug metoclopramide followed by sodium pentobarbital for the procedure.[8] It was used in the Northern Territory of Australia during the brief period in which euthanasia was permitted.[citation needed]
Capital punishment
The US state of Texas executed its first death row inmate with a single lethal injection of the sedative pentobarbital on July 18, 2012. Yokamon Hearn, 33, was convicted for the carjacking and murder of a Dallas stockbroker in 1998. [9] The sole use of Pentobarital in U.S is set to become more widespread after several states, including Ohio, Arizona, Idaho and Washington made the decision to switch following shortages of the Pancuronium bromide, a barbiturate previously used as one component in a 3-drug cocktail. [10]
The Danish manufacturer of pentobarbital, Lundbeck, expressed displeasure at this use of their product, and on July 1, 2011, announced they would block sales of the drug to U.S. prisons that carry out the death penalty.
Lundbeck adamantly opposes the distressing misuse of our product in capital punishment.[11]
They explained this decision with their commitment to UN human rights principles. [12]
Metabolism
![](http://upload.wikimedia.org/wikipedia/commons/1/15/Pentobarbital_DOJ.jpg)
Pentobarbital undergoes first-pass metabolism in the liver and possibly the intestines.[13]
Drug interactions
Administration of alcohol, opioids, antihistamines, other sedative-hypnotics, and other central nervous system depressants will cause possible additive effects.[3]
Recreational use
Pentobarbital is a drug that has been used recreationally.[14]
Chemistry
Pentobarbital is synthesized by methods analogous to that of amobarbital, the only difference being that the alkylation of α-ethylmalonic ester is carried out with 2-bromopentane (not 1-bromo-3-methylbutane) to give pentobarbital.[15][16][17]
References
- ^ "Pentobarbital Compound summary (CID4737)". Pubchem. NCBI.
- ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 9281913 , please use {{cite journal}} with
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instead. - ^ a b c "Pentobarbital". Monograph. AHFS / Drugs.com.
- ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 17901832 , please use {{cite journal}} with
|pmid= 17901832
instead. - ^ "International". Drugs.com.
- ^ "Euthanica". Euthanesia Dossier. NRC Webpagina's.
- ^ "presciption". Death with dignity act - FAQ. Public health Oregon.
- ^ "How Dignitas Works" (PDF). Dignitas. June 2010. pp. 9, 18–22. Retrieved 13 February 2012.
- ^ "Texas first single drug execution".
- ^ http://deathpenaltynews.blogspot.co.uk/2012/07/texas-executes-yokamon-hearn.html.
{{cite web}}
: Missing or empty|title=
(help) - ^ "Lundbeck overhauls pentobarbital distribution program to restrict misuse" (Press release). Lundbeck. July 1, 2011.
- ^ "Detailed position (regarding the misuse of pentobarbital)". Lundbeck.
- ^
Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 6777235 , please use {{cite journal}} with
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instead. - ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 16336040 , please use {{cite journal}} with
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instead. - ^
Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1021/ja01367a061 , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
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instead. - ^ German imperial patent, D.R.P. 293163 (1916), Bayer
- ^ GB patent 650354, Wilde, B. E. & Balaban, I. E., "Improvements in the manufacture of substituted barbituric and thiobarbituric acids", issued 1951-02-21, assigned to Geigy