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Secobarbital

Obsolete sedative-hypnotic

Secobarbital

Summary

Obsolete sedative-hypnotic

FieldValue
Watchedfieldschanged
classBarbiturate
verifiedrevid458777042
IUPAC_name(RS)-5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
imageSecobarbital.svg
image_classskin-invert-image
width150
image2SecobarbitalMV.png
image_class2bg-transparent
width2180
<!--Clinical data-->tradenameSeconal, others
Drugs.com
MedlinePlusa682386
pregnancy_categoryD (United States)
legal_BRB1
legal_BR_comment
legal_CASchedule IV
legal_DEAnlage III
legal_USSchedule II
legal_US_commentexcept when combined in a dosage unit with another active drug (in which case Schedule III)
legal_UKClass B
legal_UNP II
dependency_liabilityHigh
addiction_liabilityHigh
routes_of_administrationBy mouth, intravenous
<!--Pharmacokinetic data-->bioavailability?
protein_bound45-60%
metabolismHepatic
elimination_half-life15-40 hours
excretionRenal
<!--Identifiers-->IUPHAR_ligand7615
CAS_number_Ref
CAS_number76-73-3
ATC_prefixN05
ATC_suffixCA06
ATC_supplemental
PubChem5193
DrugBank_Ref
DrugBankDB00418
ChemSpiderID_Ref
ChemSpiderID5005
UNII_Ref
UNII1P7H87IN75
KEGG_Ref
KEGGD00430
ChEBI_Ref
ChEBI9073
ChEMBL_Ref
synonymsQuinalbarbitone
ChEMBL447
<!--Chemical data-->C12
H18
N2
O3
smilesO=C1NC(NC(C1(CC=C)C(CCC)C)=O)=O
StdInChI_Ref
StdInChI1S/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)
StdInChIKey_Ref
StdInChIKeyKQPKPCNLIDLUMF-UHFFFAOYSA-N

| Drugs.com = | elimination_half-life = 15-40 hours

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. 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 Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill) and has largely been replaced by the benzodiazepine family.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." Among barbiturates, secobarbital carries a particularly high risk of abuse and addiction, which is largely responsible for it falling out of use.

Uses

Medical

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.

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, Lupe Vélez, playwright Tennessee Williams, table tennis star Ruth Aarons and journalist Dorothy Kilgallen allegedly either died by suicide or of accidentally overdosing on secobarbital. 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.

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.

Assisted dying

Human

Secobarbital is used in assisted dying, either euthanasia or palliative sedation.

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. 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.

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.

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

Animal

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

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

Adverse effects

Possible side effects of secobarbital include:

  • Somnolence
  • Dizziness
  • Impaired motor functions
    • Impaired coordination
    • Impaired balance
  • Anxiety
  • Confusion
  • Irritability
  • Headache
  • Increased appetite
  • Nausea
  • Vomiting
  • Nightmares
  • Increased sensitivity to pain
  • Allergic reactions
    • Difficulty breathing
    • Edema
    • Urticaria

Withdrawal

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

  • Anxiety
  • Insomnia
  • Decreased appetite
  • Seizures
  • Tremors
  • Possible death as a result of withdrawal

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 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, 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, 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. 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. 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.

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

References

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. Lexi-Comp. "Secobarbital".
  3. "Propyl-Methyl Carbinyl Allyl Barbituric Acid and its Salts".
  4. (23 March 2016). "Drug Company Jacks Up Cost Of Aid-In-Dying Medication". NPR.
  5. (21 February 2018). "The dark side of Los Angeles: crime and corruption in Tinseltown – in pictures". The Guardian.
  6. (2016). "Black against empire : the history and politics of the Black Panther Party".
  7. (December 28, 1978). "How Jones Used Drugs". San Francisco Examiner.
  8. (23 March 2016). "Drug Company Jacks up Cost of Aid-In-Dying Medication". NPR.
  9. "Newly available drug secobarbital could boost number of self-administered assisted deaths".
  10. (March 2003). "Five years of legal physician-assisted suicide in Oregon". The New England Journal of Medicine.
  11. unknown. (July 29, 2010). "Hulp bij zelfdoding(Dutch)". Oncoline.
  12. (April 1, 2010). "Euthanasiedrank verliest terrein(Dutch)". Medisch contact.
  13. (April 2013). "Implementing a Death with Dignity program at a comprehensive cancer center". The New England Journal of Medicine.
  14. (January 28, 2014). "Oregon's Death with Dignity Act 2013 Report". Oregon Health Authority.
  15. (November 17, 2017). "Newly Available Drug Secobarbital Could Boost Number of Self-Administered Assisted Deaths". CBC.
  16. NIH. "Secobarbital - Human Health Effects".
  17. (August 1966). "A clinical trial of four hypnotic drugs". Canadian Medical Association Journal.
  18. (August 1986). "The antiemetic efficacy of secobarbital and chlorpromazine compared to metoclopramide, diphenhydramine, and dexamethasone. A randomized trial". Cancer.
  19. (May 1970). "Hypnotic drugs". Postgraduate Medical Journal.
  20. (January 1958). "Degree of physical dependence induced by secobarbital or pentobarbital". Journal of the American Medical Association.
  21. (March 1967). "Clinical and experimental aspects of barbiturate withdrawal convulsions". Epilepsia.
  22. (2013-07-31). "» Seconal Sodium®". Marathonpharma.com.
  23. "Marathon Pharma to Focusing Exclusively on Rare Disease".
  24. "Seconal Sodium - FDA prescribing information, side effects and uses".
  25. "Drug Shortage Detail: Secobarbital Capsules".
Wikipedia Source

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