Secobarbital

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Secobarbital
Systematic (IUPAC) name
5-[(2R)-pentan-2-yl]-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Clinical data
Trade namesSeconal
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682386
Pregnancy cat.D (United States)
Legal statusSchedule II, except when combined in a dosage unit with another active drug (in which case Schedule III) (US)
RoutesOral
Pharmacokinetic data
Bioavailability ?
Protein binding45-60%[1]
MetabolismHepatic
Half-life15-40 hours[1]
ExcretionRenal
Identifiers
CAS number76-73-3 YesY
ATC codeN05CA06 QN51AA02
PubChemCID 5193
DrugBankDB00418
ChemSpider5005 YesY
UNII1P7H87IN75 YesY
KEGGD00430 YesY
ChEBICHEBI:9073 YesY
ChEMBLCHEMBL447 YesY
Chemical data
FormulaC12H18N2O3 
Mol. mass238.283
 YesY (what is this?)  (verify)
 
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Secobarbital
Systematic (IUPAC) name
5-[(2R)-pentan-2-yl]-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
Clinical data
Trade namesSeconal
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa682386
Pregnancy cat.D (United States)
Legal statusSchedule II, except when combined in a dosage unit with another active drug (in which case Schedule III) (US)
RoutesOral
Pharmacokinetic data
Bioavailability ?
Protein binding45-60%[1]
MetabolismHepatic
Half-life15-40 hours[1]
ExcretionRenal
Identifiers
CAS number76-73-3 YesY
ATC codeN05CA06 QN51AA02
PubChemCID 5193
DrugBankDB00418
ChemSpider5005 YesY
UNII1P7H87IN75 YesY
KEGGD00430 YesY
ChEBICHEBI:9073 YesY
ChEMBLCHEMBL447 YesY
Chemical data
FormulaC12H18N2O3 
Mol. mass238.283
 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, sedative and hypnotic properties. In the United Kingdom, it was known as Quinalbarbitone.

Contents

Indications

Secobarbital is indicated for:

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 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:

Side effects

Possible side effects of secobarbital include:

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:

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" [3] 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.

Famous deaths related to use

Use in physician aid in dying

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.

References

  1. ^ a b Lexi-Comp. "Secobarbital". http://www.merck.com/mmpe/lexicomp/secobarbital.html. 
  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. ^ http://www.alwaystestclean.com/drug_definitions_n/barbiturates_drug_test.htm
  4. ^ "Queen: The Life and Music of Dinah Washington" Nadine Cohodas 2004
  5. ^ Thomson, David,Film Studies: She couldn't act for toffee - until she burst into song; The Independent; 2004-06-27; Retrieved on 2007-01-26
  6. ^ De la Parra, Adolfo "Fito" (2000). Living the Blues: Canned Heat's Story of Music, Drugs, Death, Sex and Survival. Canned Heat Music. ISBN 0-9676449-0-9. 
  7. ^ Tennessee Williams' death myth - New York Post - February 15, 2010

External links