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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. <ref {{ cite web
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. <ref> {{ cite web
| url = http://deathpenaltynews.blogspot.co.uk/2012/07/texas-executes-yokamon-hearn.html
| url = http://deathpenaltynews.blogspot.co.uk/2012/07/texas-executes-yokamon-hearn.html
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Revision as of 19:13, 20 July 2012

Pentobarbital
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa682416
Pregnancy
category
Routes of
administration		Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for animal euthanasia)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability70-90% oral; 90% rectal
Protein binding20-45%
MetabolismHepatic
Elimination half-life15-48 hours
ExcretionRenal
Identifiers
  • 5-Ethyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.895 Edit this at Wikidata
Chemical and physical data
FormulaC11H18N2O3
Molar mass226.27 g·mol−1
3D model (JSmol)
  • O=C1NC(=O)NC(=O)C1(C(C)CCC)CC
  • InChI=1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16) checkY
  • Key:WEXRUCMBJFQVBZ-UHFFFAOYSA-N checkY
  (verify)

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

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

  1. ^ "Pentobarbital Compound summary (CID4737)". Pubchem. NCBI.
  2. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 9281913 , please use {{cite journal}} with |pmid= 9281913 instead.
  3. ^ a b c "Pentobarbital". Monograph. AHFS / Drugs.com.
  4. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 17901832 , please use {{cite journal}} with |pmid= 17901832 instead.
  5. ^ "International". Drugs.com.
  6. ^ "Euthanica". Euthanesia Dossier. NRC Webpagina's.
  7. ^ "presciption". Death with dignity act - FAQ. Public health Oregon.
  8. ^ "How Dignitas Works" (PDF). Dignitas. June 2010. pp. 9, 18–22. Retrieved 13 February 2012.
  9. ^ "Texas first single drug execution".
  10. ^ http://deathpenaltynews.blogspot.co.uk/2012/07/texas-executes-yokamon-hearn.html. {{cite web}}: Missing or empty |title= (help)
  11. ^ "Lundbeck overhauls pentobarbital distribution program to restrict misuse" (Press release). Lundbeck. July 1, 2011.
  12. ^ "Detailed position (regarding the misuse of pentobarbital)". Lundbeck.
  13. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 6777235 , please use {{cite journal}} with |pmid= 6777235 instead.
  14. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 16336040 , please use {{cite journal}} with |pmid= 16336040 instead.
  15. ^ 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 |doi= 10.1021/ja01367a061 instead.
  16. ^ German imperial patent, D.R.P. 293163 (1916), Bayer
  17. ^ 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 
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