secobarbital

セコバルビタール

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/08/26 02:41:06」(JST)

wiki en

[Wiki en表示]

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 category	D (United States)
Routes of administration	Oral
Legal status
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)
Pharmacokinetic data
Bioavailability	?
Protein binding	45-60%
Metabolism	Hepatic
Biological half-life	15-40 hours
Excretion	Renal
Identifiers
CAS Number	76-73-3 Y
ATC code	N05CA06 (WHO) QN51AA02 (WHO)
PubChem	CID 5193
IUPHAR/BPS	7615
DrugBank	DB00418 Y
ChemSpider	5005 Y
UNII	1P7H87IN75 Y
KEGG	D00430 Y
ChEBI	CHEBI:9073 Y
ChEMBL	CHEMBL447 Y
Chemical data
Formula	C12H18N2O3
Molar mass	238.283
SMILES O=C1NC(NC(C1(CC=C)C(CCC)C)=O)=O
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
(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, 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.

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 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. In February 2015, Marathon sold the rights to Valeant Pharmaceuticals. 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.

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.

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 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", "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.

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. 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.

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. 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.

The LD50 of secobarbital has ben reported to be between 125 mg/kg(rat, oral) and 267 mg/kg(mouse, oral).

See also

• Tuinal

References

External links

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

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 1. 鎮静剤および催眠剤の乱用および依存：薬理学および疫学 sedatives and hypnotics abuse and dependence pharmacology and epidemiology
• 2. 不眠症の治療 treatment of insomnia
• 3. 処方剤の乱用および中毒：臨床的特徴、疫学、および寄与因子 prescription drug abuse and addiction clinical features epidemiology and contributing factors
• 4. 陣痛および分娩時の疼痛の薬理学的マネージメント pharmacologic management of pain during labor and delivery
• 5. 陣痛の潜伏相 latent phase of labor

English Journal

• [Clinical observation on fire needles at bones combined with cupping and Tuina for knee osteoarthritistis].

• Gao YL1, Yao JH, Guo JX.
• Zhongguo zhen jiu = Chinese acupuncture & moxibustion.Zhongguo Zhen Jiu.2013 Aug;33(8):697-9.
• OBJECTIVE: To explore a better therapy for knee osteoarthritis.METHODS: One hundred cases were randomly divided into a comprehensive group and an acupuncture group, 50 cases in each one. The comprehensive treatment of fire needles at bones combined with cupping and Tuina on local area of affected kn
• PMID 24195209

• Palliative care: Secobarbital in Seattle--why lose sleep?

• Chochinov HM.
• Nature reviews. Clinical oncology.Nat Rev Clin Oncol.2013 Jul;10(7):369-70. doi: 10.1038/nrclinonc.2013.88. Epub 2013 May 28.
• PMID 23712189

• Implementing a Death with Dignity program at a comprehensive cancer center.

• Loggers ET1, Starks H, Shannon-Dudley M, Back AL, Appelbaum FR, Stewart FM.
• The New England journal of medicine.N Engl J Med.2013 Apr 11;368(15):1417-24. doi: 10.1056/NEJMsa1213398.
• BACKGROUND: The majority of Death with Dignity participants in Washington State and Oregon have received a diagnosis of terminal cancer. As more states consider legislation regarding physician-assisted death, the experience of a comprehensive cancer center may be informative.METHODS: We describe the
• PMID 23574120

Japanese Journal

• Evaluation of the programmed temperature vaporiser for large-volume injection of biological samples in gas chromatography

• Journal of chromatography. B, Biomedical sciences and applications 729(1), 199-210, 1999-06-11
• NAID 10024537898

• 長期大量のバルビツール剤投与と呼吸管理を要した脳炎による難治性てんかんの治療経験

• 臨床神経学 38(5), 474-477, 1998-05-01
• NAID 10008322463

• Enhancement of hepatocarcinogenesis and induction of specific cytochrome P450-dependent monooxygenase activities by the barbiturates allobarbital, aprobarbital, pentobarbital, secobarbital and 5-phenyl- and 5-ethylbarbituric acids.

• Carcinogenesis 15, 395-402, 1994
• NAID 80007473665

Related Links

• Secobarbital: MedlinePlus Drug Information

Secobarbital may cause side effects. Tell your doctor if any of these symptoms are severe or do not go away: drowsiness difficulty falling asleep or staying asleep nightmares headache dizziness nervousness agitation

• Secobarbital | Define Secobarbital at Dictionary.com

secobarbital sec·o·bar·bi·tal (sěk'ō-bär'bĭ-tôl', -tāl') n. A white, odorless barbiturate used in the form of its sodium salt as a sedative and hypnotic.

Related Pictures

---

★リンクテーブル★

リンク元	「セコバルビタール」
拡張検索	「secobarbital sodium」

「セコバルビタール」

　　[★]

英

secobarbital

化

セコバルビタールナトリウム secobarbital sodium

商

アイオナール

「secobarbital sodium」

　　[★] セコバルビタール。セコバルビタールナトリウム