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Secobarbital

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Secobarbital
Clinical data
Trade namesSeconal, others
Other namesQuinalbarbitone
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682386
Pregnancy
category
  • D (United States)
Routes of
administration		By mouth, intravenous
Drug classBarbiturate
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
Protein binding45-60%[2]
MetabolismHepatic
Elimination half-life15-40 hours[2]
ExcretionRenal
Identifiers
  • (RS)-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.894 Edit this at Wikidata
Chemical and physical data
FormulaC12H18N2O3
Molar mass238.287 g·mol−1
3D model (JSmol)
  • O=C1NC(NC(C1(CC=C)C(CCC)C)=O)=O
  • InChI=1S/C12H18N2O3/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17) checkY
  • Key:KQPKPCNLIDLUMF-UHFFFAOYSA-N checkY
  (verify)

Secobarbital, sold under the brand name Seconal among others, is a short-acting barbiturate drug originally used for the treatment of insomnia. It was patented by Eli Lilly and Company in 1934 in the United States.[3] It possesses anesthetic, anticonvulsant, anxiolytic, sedative, and hypnotic properties. In the United Kingdom, it was known as quinalbarbitone. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill) and has largely been replaced by the benzodiazepine family. It was widely abused, known on the street as "red devils" or "reds."[4] Among barbiturates, secobarbital carries a particularly high risk of abuse and addiction, which is largely responsible for it falling out of use.

Uses

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Medical

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Secobarbital is used for managing symptoms of epilepsy and for short-term treatment of insomnia. It is also used as a preoperative medication to produce anesthesia and anxiolysis for short surgical, diagnostic, or therapeutic procedures which are minimally painful.[citation needed]

Recreational and lethal use

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Secobarbital was widely abused for recreational purposes in the 1960s, 1970s, and 1980s, and accidental overdose was associated with the drug. Lilly's Seconal came in a bright orange/red bullet shaped capsule known as a Pulvule. Prescription use of secobarbital decreased beginning in the early 1980s by which time benzodiazepines had become increasingly common. Secobarbital has acquired many nicknames, the most common being "reds," "red devils," or "red dillies" (because of the color of the capsules). Other common nicknames are "seccies," "Cardinals," "ruby slippers," and, according to the Wegman's School of Pharmacy curriculum, "red hearts". A less common nickname is "dolls"; this was partly responsible for the title of Jacqueline Susann's novel Valley of the Dolls, whose main characters use secobarbital and other such drugs.[citation needed]

Actresses Carole Landis, Judy Garland, playwright Tennessee Williams, and journalist Dorothy Kilgallen allegedly either died by suicide or of accidentally overdosing on secobarbital.[5] Seconal was used to induce Fred Hampton into docility before he was then killed in his bed in the early hours of December 4, 1969.[6]

In 1978, 1,000 pills of Seconal were recovered in Jonestown, along with substantial quantities of Valium, Thorazine, Talwin, Demerol, and other sedatives, hypnotics, and analgesics.[7]

Assisted dying

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Human

Secobarbital is used in assisted dying.[8][9][10]

In the Netherlands, individuals have two options for assisted dying: they can orally consume 100 mL of concentrated syrup containing either 15 grams of pentobarbital or 15 grams of secobarbital, or they can choose to have 2 grams of thiopental or 1 gram of propofol administered intravenously by a doctor, followed by a muscle relaxant.[11] As of 2010, only 15% of those who died by physician-assisted suicide opted for orally consuming the lethal drug(s), the rest choosing to have the drugs administered intravenously by a doctor instead.[12]

In the United States, secobarbital and pentobarbital are the most common drugs prescribed under physician aid-in-dying laws in Oregon since 1998, Washington since 2008, and Vermont since 2013.[13][14][10] Ranbaxy Laboratories Limited previously experienced various issues in their attempts to produce 100 mg secobarbital capsules.

In 2017, secobarbital was made available for physician-assisted suicide in Canada.[15]

Animal

It is a component in the veterinary drug Somulose, used for euthanasia of horses and cattle.

The LD50 of secobarbital has been reported to be between 125 mg/kg (rat, oral) and 267 mg/kg (mouse, oral).[16]

Adverse effects

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Possible side effects of secobarbital include:

Withdrawal

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Secobarbital may produce psychological addiction and produces physical dependence if used for an extended period of time.[21] Withdrawal symptoms may occur if long-term use is abruptly ended and can include:

Availability

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Secobarbital sodium, 100mg

Ranbaxy Pharmaceuticals, an India-based company now predominantly owned by the Japanese company Daiichi Sankyo, obtained the rights to market and to use the trade name Seconal from Eli Lilly in 1998 and did so until September 2008. The actual manufacturer of Seconal subsequent to the time Eli Lilly manufactured the drug was Ohm Pharmaceuticals, a wholly owned subsidiary of Ranbaxy. The rights to market Seconal were then sold to Marathon Pharmaceuticals,[23] which became the marketer and trade-name holder. At the time Marathon Pharmaceuticals obtained ownership of the brand name, the retail price for one 100 mg capsule (depending upon prescription size and pharmacy) averaged about one U.S. dollar. During the time Marathon owned the brand name, the company greatly increased the price of the drug. By February 2015, when Marathon sold the rights to Valeant Pharmaceuticals,[24] the average retail price per 100 mg capsule had risen to over thirty dollars. Since its acquisition of the trade name, Valeant Pharmaceuticals made little, if any, change to the pricing of Seconal. Despite the price increases implemented by Marathon Pharmaceuticals, Seconal was still manufactured by Ohm.[19] In the United States, Seconal is available only in 100 mg capsules, as a sodium salt. The salt is a white hygroscopic powder that is soluble in water and ethanol.

While generic versions of the drug were in existence after Eli Lilly's patent on Seconal expired, currently there are no companies that manufacture the drug generically in the United States. Until 2020, Valeant was the sole marketer of Seconal in the United States.[4] As of 2021, Valeant discontinued the product, and Bausch Health became the sole supplier of Seconal. Bausch Health stopped manufacturing the product in January 2022.[25]

Secobarbital sodium

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The sodium salt of secobarbital is classified separately from the free acid, as follows:

  • CAS number: 309-43-3
  • Chemical formula: C12H18N2NaO3
  • Molecular weight: 260.265

See also

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References

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  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ a b Lexi-Comp. "Secobarbital". Archived from the original on 2007-12-02.
  3. ^ US patent 1954429, Shonle HA, "Propyl-Methyl Carbinyl Allyl Barbituric Acid and its Salts", issued 1934-04-10, assigned to Eli Lilly 
  4. ^ a b Dembosky A (23 March 2016). "Drug Company Jacks Up Cost Of Aid-In-Dying Medication". NPR. Archived from the original on 2016-03-23. Retrieved 2016-03-24.
  5. ^ "The dark side of Los Angeles: crime and corruption in Tinseltown – in pictures". The Guardian. 21 February 2018. Archived from the original on 24 April 2018 – via www.theguardian.com.
  6. ^ Bloom J (2016). Black against empire : the history and politics of the Black Panther Party. Waldo E. Martin. Oakland. pp. 245, 237–246. ISBN 978-0-520-96645-1. OCLC 957772989.{{cite book}}: CS1 maint: location missing publisher (link)
  7. ^ King P (December 28, 1978). "How Jones Used Drugs". San Francisco Examiner.
  8. ^ https://www.npr.org/sections/health-shots/2016/03/23/471595323/drug-company-jacks-up-cost-of-aid-in-dying-medication
  9. ^ https://www.cbc.ca/news/politics/secobarbital-canada-assisted-dying-1.4406784
  10. ^ a b Hedberg K, Hopkins D, Kohn M (March 2003). "Five years of legal physician-assisted suicide in Oregon". The New England Journal of Medicine. 348 (10): 961–964. doi:10.1056/NEJM200303063481022. PMID 12621146.
  11. ^ unknown; et al. (July 29, 2010). "Hulp bij zelfdoding(Dutch)". Oncoline. Archived from the original on June 29, 2016.
  12. ^ Croonen H (April 1, 2010). "Euthanasiedrank verliest terrein(Dutch)". Medisch contact.
  13. ^ Loggers ET, Starks H, Shannon-Dudley M, Back AL, Appelbaum FR, Stewart FM (April 2013). "Implementing a Death with Dignity program at a comprehensive cancer center". The New England Journal of Medicine. 368 (15): 1417–1424. doi:10.1056/NEJMsa1213398. PMID 23574120. S2CID 23013621.
  14. ^ "Oregon's Death with Dignity Act 2013 Report" (PDF). Oregon Health Authority. January 28, 2014. Archived (PDF) from the original on November 18, 2014.
  15. ^ Bryden J (November 17, 2017). "Newly Available Drug Secobarbital Could Boost Number of Self-Administered Assisted Deaths". CBC.
  16. ^ NIH. "Secobarbital - Human Health Effects". Archived from the original on 2018-02-22.
  17. ^ a b c le Riche WH, Csima A, Dobson M (August 1966). "A clinical trial of four hypnotic drugs". Canadian Medical Association Journal. 95 (7): 300–302. PMC 1935574. PMID 5338884.
  18. ^ Richards PD, Flaum MA, Bateman M, Kardinal CG (August 1986). "The antiemetic efficacy of secobarbital and chlorpromazine compared to metoclopramide, diphenhydramine, and dexamethasone. A randomized trial". Cancer. 58 (4): 959–962. doi:10.1002/1097-0142(19860815)58:4<959::AID-CNCR2820580426>3.0.CO;2-Z. PMID 3521843. S2CID 37714069.
  19. ^ a b "Seconal Sodium - FDA prescribing information, side effects and uses". www.drugs.com. Archived from the original on 2016-04-07. Retrieved 2016-03-24.
  20. ^ Miller RR, DeYoung DV, Paxinos J (May 1970). "Hypnotic drugs". Postgraduate Medical Journal. 46 (535): 314–317. doi:10.1136/pgmj.46.535.314. PMC 2467013. PMID 5448377.
  21. ^ Fraser HF, Wikler A, Essig CF, Isbell H (January 1958). "Degree of physical dependence induced by secobarbital or pentobarbital". Journal of the American Medical Association. 166 (2): 126–129. doi:10.1001/jama.1958.02990020014002. PMID 13491317.
  22. ^ Essig CF (March 1967). "Clinical and experimental aspects of barbiturate withdrawal convulsions". Epilepsia. 8 (1): 21–30. doi:10.1111/j.1528-1157.1967.tb03816.x. PMID 5339251. S2CID 38785409.
  23. ^ "» Seconal Sodium®". Marathonpharma.com. 2013-07-31. Archived from the original on 2012-06-28. Retrieved 2014-03-05.
  24. ^ "Marathon Pharma to Focusing Exclusively on Rare Disease". Marathon Pharmaceuticals, LLC. Archived from the original on 2016-03-29. Retrieved 2016-03-24.
  25. ^ "Drug Shortage Detail: Secobarbital Capsules".
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