Secobarbital

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Secobarbital
Secobarbital2DACS.svg
Secobarbital ball-and-stick.png
Systematic (IUPAC) name
5-[(2R)-pentan-2-yl]-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Clinical data
Trade names Seconal
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a682386
Pregnancy
category
  • D (United States)
Legal status
  • CA: Schedule IV
  • DE: Anlage III (Prescription only)
  • US: Schedule II, except when combined in a dosage unit with another active drug (in which case Schedule III)
Routes of
administration		 Oral
Pharmacokinetic data
Bioavailability ?
Protein binding 45-60%[1]
Metabolism Hepatic
Biological half-life 15-40 hours[1]
Excretion Renal
Identifiers
CAS Number 76-73-3 YesY
ATC code N05CA06 (WHO) QN51AA02 (WHO)
PubChem CID: 5193
IUPHAR/BPS 7615
DrugBank DB00418 YesY
ChemSpider 5005 YesY
UNII 1P7H87IN75 YesY
KEGG D00430 YesY
ChEBI CHEBI:9073 YesY
ChEMBL CHEMBL447 YesY
Chemical data
Formula C12H18N2O3
Molecular mass 238.283
  • 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) YesY
  • Key:KQPKPCNLIDLUMF-UHFFFAOYSA-N YesY
  (verify)

Secobarbital sodium (marketed by Eli Lilly and Company, and subsequently by other companies as described below, under the brand name Seconal) is a barbiturate derivative drug that was patented in 1934 in the US.[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. [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 DOJ.jpg

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. In February 2015, Marathon sold the rights to Valeant Pharmaceuticals. [5] However Seconal is 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.

After the rights to Seconal were sold to Valeant Pharmaceuticals in 2015, Valeant immediately doubled the price in the United States from $1,500 per 100 capsules to $3,000. While generic versions of the drug used to exist after the Seconal patent expired in the early 1990s, there are currently no generics available on the US market, making Valeant the sole vendor of the drug in the US. [3]

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:

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
  • Lack of appetite
  • Seizures
  • Tremors
  • Possible death as a result of withdrawal

Recreational use

Secobarbital was widely misused in the 1960s and 1970s, and accidental overdose was associated with the drug. It was linked with the death of Judy Garland, where the postmortem found that her blood contained the equivalent of ten 1.5-grain (97 mg) Seconal capsules. Additionally the drug played a key role in the suicide of Charles Boyer in 1978. Consequently, the prescription of Seconal decreased greatly, 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" 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.

Another celebrity death attributed to secobarbital was that of Anissa Jones (a child star who played Buffy on Family Affair) on August 28, 1976. It was detected in her system, along with cocaine, PCP and methaqualone, but it was the only pharmaceutical in her toxicology report which led to homicide charges against a vendor, that being Dr. Don Carlos Moshos, who dispensed it without a proper cause or examination (as well as for Jones' recreational use), according to a postmortem criminal investigation.

Actress Lupe Velez's death was also reportedly caused by an overdose of the drug.

Secobarbital was implicated in the death of Dinah Washington. Early on the morning of December 14, 1963 Washington's seventh husband, football great Dick "Night Train" Lane, went to sleep with his wife and awoke later to find her slumped over and not responsive. Doctor B. C. Ross came to the scene and pronounced her dead. An autopsy later showed a lethal combination of secobarbital and amobarbital, which contributed to her death at the age of 39. She is buried in the Burr Oak Cemetery in Alsip, Illinois.

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.[7] 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.[8]

In the US, secobarbital and pentobarbital are the most common drugs prescribed under physician aid in dying laws in Oregon since 1998, Washington since 2008, Vermont since 2013, and New Mexico since 2014.[9][10][11] Ranbaxy Laboratories Limited previously experienced various issues in their attempts to produce 100 mg secobarbital capsules.

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

See also

References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ US patent 1954429, Shonle, H. A., "Propyl-Methyl Carbinyl Allyl Barbituric Acid and its Salts", issued 1934-04-10, assigned to Eli Lilly 
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.

External links

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