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 cat. D (United States)
Legal status Schedule II, except when combined in a dosage unit with another active drug (in which case Schedule III) (US)
Routes Oral
Pharmacokinetic data
Bioavailability ?
Protein binding 45-60%[1]
Metabolism Hepatic
Half-life 15-40 hours[1]
Excretion Renal
Identifiers
CAS number 76-73-3 YesY
ATC code N05CA06 QN51AA02
PubChem CID 5193
DrugBank DB00418
ChemSpider 5005 YesY
UNII 1P7H87IN75 YesY
KEGG D00430 YesY
ChEBI CHEBI:9073 YesY
ChEMBL CHEMBL447 YesY
Chemical data
Formula C12H18N2O3 
Mol. mass 238.283
 YesY (what is this?)  (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.

Indications[edit]

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[edit]

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 is Ohm Pharmaceuticals, a wholly owned subsidiary of Ranbaxy. The rights to market Seconal were then sold to Marathon Pharmaceuticals,[3] the current marketer / trade-name holder. However, Seconal is 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.

Secobarbital sodium[edit]

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[edit]

Possible side effects of secobarbital include:

Withdrawal[edit]

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

  • Anxiety
  • Insomnia
  • Lack of appetite
  • Seizures
  • Tremors
  • Death as a result of withdrawal

Recreational use[edit]

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.[citation needed] Consequently, 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"[4] 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. The Grateful Dead mention the drug as "reds" (Livin' on reds/Vitamin C and cocaine) in the lyrics of the song, "Truckin'".

Use in physician assisted dying[edit]

Secobarbital overdose was the most common method of implementing physician assisted dying in Oregon since 1998, Washington since 2008, Vermont since 2013, and New Mexico since 2014[citation needed]. Ranbaxy Laboratories Limited previously experienced various issues in their attempts to produce 100 mg secobarbital capsules. Currently, Marathon Pharmaceuticals is the sole marketer of the drug in the United States, although the drug remains manufactured by Ohm Laboratories.

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

See also[edit]

References[edit]

  1. ^ a b Lexi-Comp. "Secobarbital". 
  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. ^ "» Seconal Sodium®". Marathonpharma.com. 2013-07-31. Retrieved 2014-03-05. 
  4. ^ "How to Pass A Barbiturate Drug Test Facts « Always Test Clean Always Test Clean". Alwaystestclean.com. Retrieved 2014-03-05. [not in citation given]

External links[edit]