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| Formula | C18H14Cl2N2O3 |
| Molar mass | 377.22 g·mol−1 |
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Ethyl dirazepate [1] is a drug which is a benzodiazepine derivative which was developed by Sanofi Winthrop. It has anxiolytic and hypnotic and possibly other characteristic benzodiazepine properties. [2] [3] [4]
Benzodiazepines, colloquially called "benzos", are a class of depressant drugs whose core chemical structure is the fusion of a benzene ring and a diazepine ring. They are prescribed to treat conditions such as anxiety disorders, insomnia, and seizures. The first benzodiazepine, chlordiazepoxide (Librium), was discovered accidentally by Leo Sternbach in 1955, and was made available in 1960 by Hoffmann–La Roche, which followed with the development of diazepam (Valium) three years later, in 1963. By 1977, benzodiazepines were the most prescribed medications globally; the introduction of selective serotonin reuptake inhibitors (SSRIs), among other factors, decreased rates of prescription, but they remain frequently used worldwide.
Diazepam, sold under the brand name Valium among others, is a medicine of the benzodiazepine family that acts as an anxiolytic. It is used to treat a range of conditions, including anxiety, seizures, alcohol withdrawal syndrome, muscle spasms, insomnia, and restless legs syndrome. It may also be used to cause memory loss during certain medical procedures. It can be taken orally, as a suppository inserted into the rectum, intramuscularly, intravenously or used as a nasal spray. When injected intravenously, effects begin in one to five minutes and last up to an hour. When taken by mouth, effects begin after 15 to 60 minutes.
Alprazolam, sold under the brand name Xanax and others, is a fast-acting, potent tranquilizer of moderate duration within the triazolobenzodiazepine group of chemicals called benzodiazepines. Alprazolam is most commonly prescribed in the management of anxiety disorders, especially panic disorder and generalized anxiety disorder (GAD). Other uses include the treatment of chemotherapy-induced nausea, together with other treatments. GAD improvement occurs generally within a week. Alprazolam is generally taken orally.
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.
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.
Phenobarbital, also known as phenobarbitone or phenobarb, sold under the brand name Luminal among others, is a medication of the barbiturate type. It is recommended by the World Health Organization (WHO) for the treatment of certain types of epilepsy in developing countries. In the developed world, it is commonly used to treat seizures in young children, while other medications are generally used in older children and adults. It is also used for veterinary purposes. It may be administered by slow intravenous infusion, intramuscularly (IM), or orally. Subcutaneous administration is not recommended. The IV or IM may be used to treat status epilepticus if other drugs fail to achieve satisfactory results. Phenobarbital is occasionally used to treat insomnia, anxiety, and benzodiazepine withdrawal, and prior to surgery as an anxiolytic and to induce sedation. It usually begins working within five minutes when used intravenously and half an hour when administered orally. Its effects last for between four hours and two days.
Thailand's Psychotropic Substances Act is a law designed to regulate certain mind-altering drugs. According to the Office of the Narcotics Control Board, "The Act directly resulted from the Convention on Psychotropic Substances 1971 of which Thailand is a party." The Act divides psychotropic drugs into four Schedules. Offenses involving Schedule I and II drugs carry heavier penalties than those involving Schedule III and IV drugs. Note that this statute does not regulate most opioids, cocaine, or some amphetamines. The vast majority of narcotic painkillers, along with cocaine and most amphetamines are regulated under the Narcotics Act.
The Controlled Drugs and Substances Act is Canada's federal drug control statute. Passed in 1996 under Prime Minister Jean Chrétien's government, it repeals the Narcotic Control Act and Parts III and IV of the Food and Drugs Act, and establishes eight Schedules of controlled substances and two Classes of precursors. It provides that "The Governor in Council may, by order, amend any of Schedules I to VIII by adding to them or deleting from them any item or portion of an item, where the Governor in Council deems the amendment to be necessary in the public interest."
Adinazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It possesses anxiolytic, anticonvulsant, sedative, and antidepressant properties. Adinazolam was developed by Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed. Adinazolam was never FDA approved and never made available to the public market; however, it has been sold as a designer drug.
Ethyl loflazepate is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. In animal studies it was found to have low toxicity, although in rats evidence of pulmonary phospholipidosis occurred with pulmonary foam cells developing with long-term use of very high doses. Its elimination half-life is 51–103 hours. Its mechanism of action is similar to other benzodiazepines. Ethyl loflazepate also produces an active metabolite which is stronger than the parent compound. Ethyl loflazepate was designed to be a prodrug for descarboxyloflazepate, its active metabolite. It is the active metabolite which is responsible for most of the pharmacological effects rather than ethyl loflazepate. The main metabolites of ethyl loflazepate are descarbethoxyloflazepate, loflazepate and 3-hydroxydescarbethoxyloflazepate. Accumulation of the active metabolites of ethyl loflazepate are not affected by those with kidney failure or impairment. The symptoms of an overdose of ethyl loflazepate include sleepiness, agitation and ataxia. Hypotonia may also occur in severe cases. These symptoms occur much more frequently and severely in children. Death from therapeutic maintenance doses of ethyl loflazepate taken for 2 – 3 weeks has been reported in 3 elderly patients. The cause of death was asphyxia due to benzodiazepine toxicity. High doses of the antidepressant fluvoxamine may potentiate the adverse effects of ethyl loflazepate.
Pagoclone is an anxiolytic agent from the cyclopyrrolone family, related to better-known drugs such as the sleeping medication zopiclone. It was synthesized by a French team working for Rhone-Poulenc & Rorer S.A. Pagoclone belongs to the class of nonbenzodiazepines, which have similar effects to the older benzodiazepine group, but with quite different chemical structures. It was never commercialised.
DMCM is a drug from the β-carboline family that induces anxiety and convulsions by acting as a negative allosteric modulator of GABAA receptors — functionally opposite to benzodiazepines and related drugs which are positive allosteric modulators — and is used in scientific research for these properties to test new anxiolytic and anticonvulsant medications, respectively. It has also been shown to produce analgesic effects in animals, which is thought to be the drug's induced panic reducing the perception of pain.
Ro15-4513(IUPAC: Ethyl-8-azido-5,6-dihydro-5-methyl-6-oxo-4H-imidazo-1,4-benzodiazepine-3-carboxylate) is a weak partial inverse agonist of the benzodiazepine class of drugs, developed by Hoffmann–La Roche in the 1980s. It acts as an inverse agonist, and can therefore be an antidote to the acute impairment caused by alcohols, including ethanol, isopropanol, tert-butyl alcohol, tert-amyl alcohol, 3-methyl-3-pentanol, methylpentynol and ethchlorvynol.
Pipequaline (INN) is an anxiolytic drug that was never marketed. It possesses a novel chemical structure that is not closely related to other drugs of this type. The drug has a similar pharmacological profile to the benzodiazepine family of drugs, but with mainly anxiolytic properties and very little sedative, amnestic or anticonvulsant effects, and so is classified as a nonbenzodiazepine anxiolytic.
TPA-023 (MK-0777) is an anxiolytic drug with a novel chemical structure, which is used in scientific research. It has similar effects to benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine anxiolytic. It is a mixed, subtype-selective ligand of the benzodiazepine site of α1, α2, α3, and α5-containing GABAA receptors, where it acts as a partial agonist at benzodiazepine sites of the α2 and α3-containing subtypes, but as a silent antagonist at α1 and α5-containing subtypes. It has primarily anxiolytic and anticonvulsant effects in animal tests, but with no sedative effects even at 50 times the effective anxiolytic dose.
ZK-93426 (ethyl-5-isopropoxy-4-methyl-beta-carboline-3-carboxylate) is a drug from the beta-carboline family. It acts as a weak partial inverse agonist of benzodiazepine receptors, meaning that it causes the opposite effects to the benzodiazepine class of drugs and has anxiogenic properties, although unlike most benzodiazepine antagonists it is not a convulsant and actually has weak anticonvulsant effects. In human tests it produced alertness, restlessness and feelings of apprehension, and reversed the effect of the benzodiazepine lormetazepam. It was also shown to produce nootropic effects and increased release of acetylcholine.
ZK-93423 is an anxiolytic drug from the β-Carboline family, closely related to abecarnil. It is a nonbenzodiazepine GABAA agonist which is not subtype selective and stimulates α1, α2, α3, and α5-subunit containing GABAA receptors equally. It has anticonvulsant, muscle relaxant and appetite stimulating properties comparable to benzodiazepine drugs. ZK-93423 has also been used as a base to develop new and improved beta-carboline derivatives and help map the binding site of the GABAA receptor.
Ethyl carfluzepate is a drug which is a benzodiazepine derivative. It is similar to ethyl loflazepate in chemical structure, the other difference being an absence of methylcarbamoyl group. Its properties are mainly sedative and hypnotic.
N-Desalkylflurazepam is a benzodiazepine analog and an active metabolite of several other benzodiazepine drugs including flurazepam, flutoprazepam, fludiazepam, midazolam, flutazolam, quazepam, and ethyl loflazepate. It is long-acting, prone to accumulation, and binds unselectively to the various benzodiazepine receptor subtypes. It has been sold as a designer drug from 2016 onward.
Flumezapine is an abandoned, investigational antipsychotic drug that was studied for the treatment of schizophrenia. Flumezapine failed clinical trials due to concern for liver and muscle toxicity. Flumezapine is structurally related to the common antipsychotic olanzapine—a point that was used against its manufacturer, Eli Lilly and Company, in a lawsuit in which generic manufacturers sought to void the patent on brand name olanzapine (Zyprexa). Although flumezapine does not differ greatly from olanzapine in terms of its structure, the difference was considered to be non-obvious, and Eli Lilly's patent rights on Zyprexa were upheld.
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