Secobarbital

Secobarbital

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%
Metabolism	Hepatic
Half-life	15-40 hours
Excretion	Renal
Identifiers
CAS number	76-73-3 Y
ATC code	N05CA06 QN51AA02
PubChem	CID 5193
DrugBank	DB00418
ChemSpider	5005 Y
UNII	1P7H87IN75 Y
KEGG	D00430 Y
ChEBI	CHEBI:9073 Y
ChEMBL	CHEMBL447 Y
Chemical data
Formula	C12H18N2O3
Mol. mass	238.283
SMILES O=C1NC(=O)NC(=O)C1(C(C)CCC)C\C=C
InChI 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) Y Key:KQPKPCNLIDLUMF-UHFFFAOYSA-N Y
Y (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. It possesses anaesthetic, anticonvulsant, sedative, and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.

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

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, the current marketer / trade-name holder. However, Seconal is still manufactured by Ohm. Marathon has significantly raised the Average Wholesale Price ("AWP") of Seconal. This is noteworthy because of degree. As of August 2012, the AWP of Seconal is almost fifteen times that of what it was when Ranbaxy held the trade name, and roughly one hundred fifty times that of what it was in 1982. 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

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
• Impaired motor functions
  • Impaired coordination
  • Impaired balance
  • Dizziness
• Anxiety
• Confusion
• Agitation, irritability, or excitability
• Headache
• Nausea
• Vomiting
• Nightmares
• Increased sensitivity to pain
• Allergic reactions
  • Difficulty breathing
  • Edema
  • Urticaria

Withdrawal

Secobarbital may be both psychologically and physically addictive 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

Secobarbital was widely misused in the 1960s and 1970s, and accidental overdose was associated with the drug. 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" 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.

Use in physician-assisted suicide

Secobarbital overdose was the most common method of implementing physician assisted suicide in Oregon for many years. Subsequently, pentobarbital has dominated in Oregon PAD. 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

• Tuinal

External links

• Marathon Pharmaceuticals - Seconal Full prescribing information for the United States.
• Drugs.com - Secobarbital
• RxList.com - Secobarbital Consumer information.