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Clinical data | |
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Trade names | Seconal, others |
Other names | Quinalbarbitone |
AHFS/Drugs.com | Consumer Drug Information |
MedlinePlus | a682386 |
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Routes of administration | By mouth, intravenous |
Drug class | Barbiturate |
ATC code | |
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Pharmacokinetic data | |
Bioavailability | ? |
Protein binding | 45-60% [2] |
Metabolism | Hepatic |
Elimination half-life | 15-40 hours [2] |
Excretion | Renal |
Identifiers | |
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ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.894 |
Chemical and physical data | |
Formula | C12H18N2O3 |
Molar mass | 238.287 g·mol−1 |
3D model (JSmol) | |
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Secobarbital, sold under the brand name Seconal among others, is a short-acting barbiturate drug originally used for the treatment of insomnia. It was patented by Eli Lilly and Company in 1934 in the United States. [3] It possesses anesthetic, anticonvulsant, anxiolytic, sedative, and hypnotic properties. In the United Kingdom, it was known as quinalbarbitone. Secobarbital is considered to be an obsolete sedative-hypnotic (sleeping pill) and has largely been replaced by the benzodiazepine family. It was widely abused, known on the street as "red devils" or "reds." [4] Among barbiturates, secobarbital carries a particularly high risk of abuse and addiction, which is largely responsible for it falling out of use.
Secobarbital is indicated for:
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 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, [5] which became the marketer and trade-name holder. At the time Marathon Pharmaceuticals obtained ownership of the brand name, the retail price for one 100 mg capsule (depending upon prescription size and pharmacy) averaged about one U.S. dollar. During the time Marathon owned the brand name, the company greatly increased the price of the drug. By February 2015, when Marathon sold the rights to Valeant Pharmaceuticals, [6] the average retail price per 100 mg capsule had risen to over thirty dollars. Since its acquisition of the trade name, Valeant Pharmaceuticals made little, if any, change to the pricing of Seconal. Despite the price increases implemented by Marathon Pharmaceuticals, Seconal was still manufactured by Ohm. [7] 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.
While generic versions of the drug were in existence after Eli Lilly's patent on Seconal expired, currently there are no companies that manufacture the drug generically in the United States. Until 2020, Valeant was the sole marketer of Seconal in the United States. [4] As of 2021, Valeant discontinued the product, and Bausch Health became the sole supplier of Seconal. Bausch Health stopped manufacturing the product in January 2022. [8]
The sodium salt of secobarbital is classified separately from the free acid, as follows:
Possible side effects of secobarbital include:
Secobarbital may produce psychological addiction and produces physical dependence if used for an extended period of time. [12] Withdrawal symptoms may occur if long-term use is abruptly ended and can include:
Secobarbital was widely abused for recreational purposes in the 1960s, 1970s, and 1980s, and accidental overdose was associated with the drug. Lilly's Seconal came in a bright orange/red bullet shaped capsule known as a Pulvule. Prescription use of secobarbital decreased 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.
Actresses Carole Landis, Judy Garland, playwright Tennessee Williams, and journalist Dorothy Kilgallen allegedly either died by suicide or of accidentally overdosing on secobarbital. [14] Seconal was used to induce Fred Hampton into docility before he was then killed in his bed in the early hours of December 4, 1969. [15]
In 1978, 1,000 pills of Seconal were recovered in Jonestown, along with substantial quantities of Valium, Thorazine, Talwin, Demerol, and other sedatives, hypnotics, and analgesics. [16]
Secobarbital is used in assisted dying. [17] [18] [19]
In the Netherlands, individuals have two options for assisted dying: 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. [20] As of 2010, only 15% of those who died by physician-assisted suicide opted for orally consuming the lethal drug(s), the rest choosing to have the drugs administered intravenously by a doctor instead. [21]
In the United States, secobarbital and pentobarbital are the most common drugs prescribed under physician aid-in-dying laws in Oregon since 1998, Washington since 2008, and Vermont since 2013. [22] [23] [19] Ranbaxy Laboratories Limited previously experienced various issues in their attempts to produce 100 mg secobarbital capsules.
In 2017, secobarbital was made available for physician-assisted suicide in Canada. [24]
It is a component in the veterinary drug Somulose, used for euthanasia of horses and cattle.
The LD50 of secobarbital has been reported to be between 125 mg/kg (rat, oral) and 267 mg/kg (mouse, oral). [25]
Hypnotic, or soporific drugs, commonly known as sleeping pills, are a class of psychoactive drugs whose primary function is to induce sleep and to treat insomnia (sleeplessness).
Sodium thiopental, also known as Sodium Pentothal, thiopental, thiopentone, or Trapanal, is a rapid-onset short-acting barbiturate general anesthetic. It is the thiobarbiturate analog of pentobarbital, and an analog of thiobarbital. Sodium thiopental was a core medicine in the World Health Organization's List of Essential Medicines, but was supplanted by propofol. Despite this, thiopental is listed as an acceptable alternative to propofol, depending on local availability and cost of these agents. It was the first of three drugs administered during most lethal injections in the United States until the US division of Hospira objected and stopped manufacturing the drug in 2011, and the European Union banned the export of the drug for this purpose. Although thiopental abuse carries a dependency risk, its recreational use is rare.
Temazepam, sold under the brand name Restoril among others, is a medication of the benzodiazepine class which is generally used to treat severe or debilitating insomnia. It is taken by mouth. Temazepam is rapidly absorbed, and significant hypnotic effects begin in less than 30 minutes and can last for up to eight hours. Prescriptions for hypnotics such as temazepam have seen a dramatic decrease since 2010, while anxiolytics such as alprazolam, clonazepam, and lorazepam have increased or remained stable. Temazepam and similar hypnotics, such as triazolam (Halcion) are generally reserved for severe and debilitating insomnia. They have largely been replaced by z-drugs and atypical antidepressants as first line treatment for insomnia.
Chloral hydrate is a geminal diol with the formula Cl3C−CH(OH)2. It was first used as a sedative and hypnotic in Germany in the 1870s. Over time it was replaced by safer and more effective alternatives but it remained in usage in the United States until at least the 1970s. It sometimes finds usage as a laboratory chemical reagent and precursor. It is derived from chloral (trichloroacetaldehyde) by the addition of one equivalent of water.
A sedative or tranquilliser is a substance that induces sedation by reducing irritability or excitement. They are CNS depressants and interact with brain activity causing its deceleration. Various kinds of sedatives can be distinguished, but the majority of them affect the neurotransmitter gamma-aminobutyric acid (GABA). In spite of the fact that each sedative acts in its own way, most produce relaxing effects by increasing GABA activity.
Ethchlorvynol is a GABA-ergic sedative and hypnotic/soporific medication first developed by Pfizer in the 1950s. In the United States it was sold by Abbott Laboratories under the trade name Placidyl. Placidyl was available in 200 mg, 500 mg, and 750 mg strength gel filled capsules. While the 500 mg and 750 mg strength capsules were for use in reducing sleep latency, the 200 mg strength capsules were intended to be used to re-induce sleep in case of early awakening. Abbott discontinued production in 1999, due to it being replaced by the benzodiazepine family and its widespread abuse, after which Placidyl was available for about a year in the United States. Although, theoretically, ethchlorvynol could be manufactured for sale in the United States by another pharmaceutical company, no pharmaceutical company has chosen to do so. Individuals with a valid prescription for the substance may legally transport a reasonable amount of ethclorvynol with them into the United States.
Tuinal was the brand name of a discontinued combination drug composed of two barbiturate sodium salts in equal proportions.
Flurazepam is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties. It produces a metabolite with a long half-life, which may stay in the bloodstream for days. Flurazepam was patented in 1968 and came into medical use the same year. Flurazepam, developed by Roche Pharmaceuticals, was one of the first benzodiazepine hypnotic medications to be marketed.
Amobarbital is a drug that is a barbiturate derivative. It has sedative-hypnotic properties. It is a white crystalline powder with no odor and a slightly bitter taste. It was first synthesized in Germany in 1923. It is considered a short to intermediate acting barbiturate.
Eszopiclone, sold under the brand name Lunesta among others, is a medication used in the treatment of insomnia. Evidence supports slight to moderate benefit up to six months. It is taken by mouth.
Zaleplon, sold under the brand name Sonata among others, is a sedative and hypnotic which is used to treat insomnia. It is a nonbenzodiazepine or Z-drug of the pyrazolopyrimidine class. It was developed by King Pharmaceuticals and approved for medical use in the United States in 1999.
Pentobarbital (US) or pentobarbitone is a short-acting barbiturate typically used as a sedative, a preanesthetic, and to control convulsions in emergencies. It can also be used for short-term treatment of insomnia but has been largely replaced by the benzodiazepine family of drugs.
Butabarbital is a prescription barbiturate sleep aid and anxiety medication. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia, relieving general anxiety and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its intermediate duration of action gives butabarbital an abuse potential slightly lower than secobarbital. Butabarbital can be hydrolyzed to valnoctamide.
Clomethiazole is a sedative and hypnotic originally developed by Hoffmann-La Roche in the 1930s. The drug is used in treating and preventing symptoms of acute alcohol withdrawal.
Mebutamate is an anxiolytic and sedative drug with antihypertensive effects of the carbamate class. It has effects comparable to those of barbiturates such as secobarbital, but is only around 1/3 the potency of secobarbital as a sedative. Side effects include dizziness and headaches.
Brallobarbital was a barbiturate developed in the 1920s. It has sedative and hypnotic properties, and was used for the treatment of insomnia. Brallobarbital was primarily sold as part of a combination product called Vesparax, composed of 150 mg secobarbital, 50 mg brallobarbital and 50 mg hydroxyzine. The long half-life of this combination of drugs tended to cause a hangover effect the next day, and Vesparax fell into disuse once newer drugs with lesser side effects had been developed. Vesparax reportedly was the drug that musician Jimi Hendrix supposedly overdosed on and led to his untimely death. It is no longer made.
Crotylbarbital, also known as crotarbital, is a barbiturate derivative developed by Eli Lilly in the 1930s. It has sedative and hypnotic effects, and was used for the treatment of insomnia until it was replaced by newer alternative drugs with fewer side effects and lower risk of overdose.
Desbutal was a brand name drug by Abbott containing 5 mg methamphetamine hydrochloride (Desoxyn) and 30 mg pentobarbital sodium (Nembutal); a substituted amphetamine and a barbiturate combined within the same pill. Desbutal was marketed as an antidepressant as well as a medication for the treatment of obesity, narcolepsy, parkinsonism, and alcoholism, although it was commonly also prescribed off-label for miscellaneous ailments. It had a high abuse potential and is no longer manufactured.
Barbiturates are a class of depressant drugs that are chemically derived from barbituric acid. They are effective when used medically as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as well as overdose potential among other possible adverse effects. They have been used recreationally for their anti-anxiety and sedative effects, and are thus controlled in most countries due to the risks associated with such use.
Barbiturate dependence develops with regular use of barbiturates. This in turn may lead to a need for increasing doses of the drug to get the original desired pharmacological or therapeutic effect. Barbiturate use can lead to both addiction and physical dependence, and as such they have a high potential for excess or non-medical use, however, it does not affect all users. Management of barbiturate dependence involves considering the affected person's age, comorbidity and the pharmacological pathways of barbiturates.
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