Chemistry:Secobarbital

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Short description: Obsolete sedative-hypnotic
Secobarbital
Secobarbital2DACS.svg
Secobarbital ball-and-stick.png
Clinical data
Trade namesSeconal
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682386
Pregnancy
category
  • D (United States)
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
Protein binding45-60%[1]
MetabolismHepatic
Elimination half-life15-40 hours[1]
ExcretionRenal
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC12H18N2O3
Molar mass238.283 g·mol−1
3D model (JSmol)
  (verify)

Secobarbital (as the sodium salt, originally marketed by Eli Lilly and Company for the treatment of insomnia, and subsequently by other companies as described below, under the brand name Seconal) is a short-acting barbiturate derivative drug that was patented in 1934 in the United States.[2] It possesses anaesthetic, anticonvulsant, anxiolytic, sedative, and hypnotic properties. In the United Kingdom, it was known as quinalbarbitone. It is the most frequently used drug in physician-assisted suicide within the United States. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill), and as a result, it has largely been replaced by the benzodiazepine family. Seconal was widely abused, known on the street as "red devils" or "reds".[3]

Indications

Secobarbital is indicated for:

  • Treatment of epilepsy
  • Temporary treatment of insomnia
  • Use as a preoperative medication to produce anaesthesia and anxiolysis in short surgical, diagnostic, or therapeutic procedures which are minimally painful.

Availability

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 18, 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,[4] 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,[5] 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.[6] 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 of the name 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.[3] 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.[7]

Secobarbital sodium

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

Side effects

Possible side effects of secobarbital include:

  • Somnolence[8]
  • Impaired motor functions
  • Anxiety
  • Confusion
  • Agitation, irritability, or excitability
  • Headache[8]
  • Hunger
  • Nausea
  • Vomiting
  • Nightmares
  • Increased sensitivity to pain
  • Allergic reactions

Withdrawal

Secobarbital may produce psychological addiction and produces physical dependence if used for an extended period of time.[11] Withdrawal symptoms may occur if long-term use is abruptly ended and can include:

  • Anxiety
  • Insomnia
  • Lack of appetite
  • Seizures[12]
  • Tremors
  • Possible death as a result of withdrawal

Recreational and lethal use

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. Actresses Carole Landis, Judy Garland, playwright Tennessee Williams, and journalist Dorothy Kilgallen allegedly either died by suicide or of accidentally overdosing on secobarbital.[13] 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.[14]

In 1978, 1000 pills of Seconal were recovered in Jonestown, along with substantial quantities of Valium, Thorazine, Talwin, Demerol, and other sedatives, hypnotics, and analgesics.[15]

Use in animal and human euthanasia

In the Netherlands, individuals have two options for euthanasia. 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.[16] In recent years only 15% of those who died by euthanasia opted for orally consuming the lethal drug(s), the rest choosing to have the drugs administered intravenously by a doctor instead.[17]

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. [18][19][20] 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.[21]

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

The -1">50 of secobarbital has been reported to be between 125 mg/kg (rat, oral) and 267 mg/kg (mouse, oral).[22]

See also

References

  1. ↑ 1.0 1.1 Lexi-Comp. "Secobarbital". http://www.merck.com/mmpe/lexicomp/secobarbital.html. 
  2. ↑ Shonle HA, "Propyl-Methyl Carbinyl Allyl Barbituric Acid and its Salts", US patent 1954429, issued 1934-04-10, assigned to Eli Lilly
  3. ↑ 3.0 3.1 "Drug Company Jacks Up Cost Of Aid-In-Dying Medication". NPR. 23 March 2016. https://www.npr.org/sections/health-shots/2016/03/23/471595323/drug-company-jacks-up-cost-of-aid-in-dying-medication. 
  4. ↑ "» Seconal Sodium®". Marathonpharma.com. 2013-07-31. http://marathonpharma.com/products/seconal-sodium. 
  5. ↑ "Marathon Pharma to Focusing Exclusively on Rare Disease" (in en-US). http://marathonpharma.com/news/2015/02/marathon-pharmaceuticals-llc-divests-non-strategic-products-focus-exclusively-rare-disease-treatments/. 
  6. ↑ 6.0 6.1 "Seconal Sodium - FDA prescribing information, side effects and uses". https://www.drugs.com/pro/seconal-sodium.html. 
  7. ↑ "Drug Shortage Detail: Secobarbital Capsules". https://www.ashp.org/drug-shortages/current-shortages/drug-shortage-detail.aspx?id=517&loginreturnUrl=SSOCheckOnly. 
  8. ↑ 8.0 8.1 8.2 "A clinical trial of four hypnotic drugs". Canadian Medical Association Journal 95 (7): 300–302. August 1966. PMID 5338884. 
  9. ↑ "The antiemetic efficacy of secobarbital and chlorpromazine compared to metoclopramide, diphenhydramine, and dexamethasone. A randomized trial". Cancer 58 (4): 959–962. August 1986. doi:10.1002/1097-0142(19860815)58:4<959::AID-CNCR2820580426>3.0.CO;2-Z. PMID 3521843. 
  10. ↑ "Hypnotic drugs". Postgraduate Medical Journal 46 (535): 314–317. May 1970. doi:10.1136/pgmj.46.535.314. PMID 5448377. 
  11. ↑ "Degree of physical dependence induced by secobarbital or pentobarbital". Journal of the American Medical Association 166 (2): 126–129. January 1958. doi:10.1001/jama.1958.02990020014002. PMID 13491317. 
  12. ↑ "Clinical and experimental aspects of barbiturate withdrawal convulsions". Epilepsia 8 (1): 21–30. March 1967. doi:10.1111/j.1528-1157.1967.tb03816.x. PMID 5339251. 
  13. ↑ "The dark side of Los Angeles: crime and corruption in Tinseltown – in pictures". The Guardian. 21 February 2018. https://www.theguardian.com/artanddesign/gallery/2018/feb/21/the-dark-side-of-los-angeles-and-corruption-in-tinseltown-in-pictures. 
  14. ↑ Black against empire : the history and politics of the Black Panther Party. Waldo E. Martin. Oakland. 2016. pp. 245;237–246. ISBN 978-0-520-96645-1. OCLC 957772989. https://www.worldcat.org/oclc/957772989. 
  15. ↑ "How Jones Used Drugs". San Francisco Examiner. December 28, 1978. 
  16. ↑ unknown (July 29, 2010). "Hulp bij zelfdoding(Dutch)". Oncoline. http://www.oncoline.nl/index.php?pagina=/richtlijn/item/pagina.php&id=32169&richtlijn_id=754. 
  17. ↑ "Euthanasiedrank verliest terrein(Dutch)". Medisch contact. April 1, 2010. http://www.medischcontact.nl/archief-6/Tijdschriftartikel/75650/Euthanasiedrank-verliest-terrein.htm. 
  18. ↑ "Implementing a Death with Dignity program at a comprehensive cancer center". The New England Journal of Medicine 368 (15): 1417–1424. April 2013. doi:10.1056/NEJMsa1213398. PMID 23574120. 
  19. ↑ "Oregon's Death with Dignity Act 2013 Report". Oregon Health Authority. January 28, 2014. http://public.health.oregon.gov/ProviderPartnerResources/EvaluationResearch/DeathwithDignityAct/Documents/year16.pdf. 
  20. ↑ "Five years of legal physician-assisted suicide in Oregon". The New England Journal of Medicine 348 (10): 961–964. March 2003. doi:10.1056/NEJM200303063481022. PMID 12621146. 
  21. ↑ "Newly Available Drug Secobarbital Could Boost Number of Self-Administered Assisted Deaths". CBC. November 17, 2017. https://www.cbc.ca/news/politics/secobarbital-canada-assisted-dying-1.4406784. 
  22. ↑ NIH. "Secobarbital - Human Health Effects". https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+3182. 

External links



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