Pentobarbital
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| Systematic (IUPAC) name | |
| 5-Ethyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione | |
| Clinical data | |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682416 |
| Pregnancy cat. | D (USA) |
| Legal status | USA: Schedule II (oral and parenteral); Schedule III (rectal), UK: Class B Controlled Substance |
| Routes | Oral, Intravenous, Intramuscular, Rectal; also Intraperitoneal & Intracardiac (for animal euthanasia) |
| Pharmacokinetic data | |
| Bioavailability | 70-90% oral; 90% rectal |
| Protein binding | 20-45% |
| Metabolism | Hepatic |
| Half-life | 15-48 hours |
| Excretion | Renal |
| Identifiers | |
| CAS number | 76-74-4  |
| ATC code | N05CA01 QN51AA01 |
| PubChem | CID 4737 |
| DrugBank | APRD01174 |
| ChemSpider | 4575 |
| UNII | I4744080IR |
| KEGG | D00499 |
| ChEBI | CHEBI:7983 |
| ChEMBL | CHEMBL448 |
| Chemical data | |
| Formula | C11H18N2O3 |
| Mol. mass | 226.27 |
| SMILES | eMolecules & PubChem |
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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]
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[edit] Uses
[edit] 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]
[edit] 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]
[edit] 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]
[edit] Human euthanasia
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.[6]
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.[7] It is also used in the Netherlands, and was used in the Northern Territory of Australia during the brief period in which euthanasia was permitted.[citation needed]
[edit] Capital punishment
Pentobarbital has been approved or considered for use in executions in various U.S. states.[8]
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 is dedicated to saving people’s lives. Use of our products to end lives contradicts everything we are in business to do. Lundbeck is opposed to the use of its product for the purpose of capital punishment.[9]
They explained this decision with their commitment to UN human rights principles. [8]
[edit] Metabolism
Pentobarbital undergoes first-pass metabolism in the liver and possibly the intestines.[10]
[edit] Drug interactions
Administration of alcohol, opioids, antihistamines, other sedative-hypnotics, and other central nervous system depressants will cause possible additive effects.[3]
[edit] Recreational use
Pentobarbital is a drug that has been used recreationally.[11]
[edit] 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.[12][13][14]
[edit] References
- ^ "Pentobarbital Compound summary (CID4737)". Pubchem. NCBI. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=4737.
- ^ Fosburgh, L. C. (1997). "From this point in time: Some memories of my part in the history of anesthesia--John S. Lundy, MD". AANA journal 65 (4): 323–328. PMID 9281913.
- ^ a b c "Pentobarbital". Monograph. AHFS / Drugs.com. http://www.drugs.com/monograph/pentobarbital.html.
- ^ Stravitz, R. T.; Kramer, A. H.; Davern, T.; Shaikh, A. O. S.; Caldwell, S. H.; Mehta, R. L.; Blei, A. T.; Fontana, R. J. et al (2007). "Intensive care of patients with acute liver failure: Recommendations of the U.S. Acute Liver Failure Study Group". Critical Care Medicine 35 (11): 2498–2508. doi:10.1097/01.CCM.0000287592.94554.5F. PMID 17901832.
- ^ "International". Drugs.com. http://www.drugs.com/international/pentobarbital.html.
- ^ "presciption". Death with dignity act - FAQ. Public health Oregon. http://public.health.oregon.gov/ProviderPartnerResources/EvaluationResearch/DeathwithDignityAct/Pages/faqs.aspx#prescription.
- ^ "How Dignitas Works". Dignitas. June 2010. pp. 9; 18-22. http://www.dignitas.ch/images/stories/pdf/so-funktioniert-dignitas-e.pdf. Retrieved 13 February 2012.
- ^ a b "Detailed position (regarding the misuse of pentobarbital)". Lundbeck. http://www.lundbeck.com/global/media/detailed-position.
- ^ "Lundbeck's position regarding the misuse of pentobarbital" (Press release). Lundbeck. July 1, 2011. http://www.lundbeck.com/global/media/lundbecks-position-regarding-the-misuse-of-pentobarbital.
- ^ Knodell, R. G.; Spector, M. H.; Brooks, D. A.; Keller, F. X.; Kyner, W. T. (1980). "Alterations in pentobarbital pharmacokinetics in response to parenteral and enteral alimentation in the rat". Gastroenterology 79 (6): 1211–1216. PMID 6777235.
- ^ Griffiths, R. R.; Johnson, M. W. (2005). "Relative abuse liability of hypnotic drugs: A conceptual framework and algorithm for differentiating among compounds" (pdf). The Journal of clinical psychiatry 66 Suppl 9: 31–41. PMID 16336040. http://neuroscience.jhu.edu/griffiths%20papers/v66s0906.pdf.
- ^ Volwiler, E. H.; Tabern, D. L. (1930). "5,5-SUBSTITUTED BARBITURIC ACIDS". Journal of the American Chemical Society 52 (4): 1676–1679. doi:10.1021/ja01367a061.
- ^ 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
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