Fenadiazole
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Fenadiazole (), also known as phénadiazole () and sold under the brand names Hypnazol, Eudormil, and Viodor, is a
hypnotic Hypnotic (from Greek ''Hypnos'', sleep), or soporific drugs, commonly known as sleeping pills, are a class of (and umbrella term for) psychoactive drugs whose primary function is to induce sleep (or surgical anesthesiaWhen used in anesthesia ...
and
sedative 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 ...
medication which has been used to treat
insomnia Insomnia, also known as sleeplessness, is a sleep disorder in which people have trouble sleeping. They may have difficulty falling asleep, or staying asleep as long as desired. Insomnia is typically followed by daytime sleepiness, low energy, ...
but is no longer marketed. It is described as a non-
barbiturate 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 a ...
hypnotic with marked or profound hypnotic and sedative properties in animals, variable hypnotic effects in humans (rapidly inducing sleep for 6 to 8hours), additional
anticonvulsant Anticonvulsants (also known as antiepileptic drugs or recently as antiseizure drugs) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of ...
, antithermal, and spasmolytic effects, and a generally well-tolerated profile in humans (at an average dosage of 200mg/day). Abstract: 2-(o-Hydroxyphenyl)-1,3,4-oxadiazole (I) rapidly induced sleep for a duration of 6-8 hrs. in man. I is prepd. in 92.5% yield by refluxing a mixt. of 431 g. salicylic acid hydrazide, 800 cc. HC(OEt)3, and 2350 cc. xylene. Approx. 390 g. EtOH is distd.; the remaining hot soln. is filtered and cooled to 0°. Crystals of I formed are washed with xylene, then with petr. ether and dried. Given intraperitoneally, L.D.50 is 940 mg./kg. for mice; 910 mg./kg. for the rats; orally it is 4.72 mg./kg. for mice. Abstract: The title compds., possessed marked hypnotic and sedative properties, were prepd. by heating salicylic acid hydrazide (I) with an alkyl orthoformate (excess) and removing the alc. corresponding to the alkyl group of the selected orthoformate by continuous distn. Thus, 431 g. I, 800 ml. ethyl orthoformate, and 2350 ml. xylene was refluxed while stirring and the alc. removed continuously by distn. After 6 hrs., the hot soln. was filtered, and cooled (0°) to give 2-(o-hydroxyphenyl)-1,3,4-​oxadiazole (II), m. 109-10°, in 92.5% yield. Derivs. of II were obtained by replacing the H atom of the phenolic hydroxyl by metals. The drug was synthesized, pharmacologically characterized,
patent A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an enabling disclosure of the invention."A ...
ed, and marketed by the French
pharmaceutical company The pharmaceutical industry discovers, develops, produces, and markets drugs or pharmaceutical drugs for use as medications to be administered to patients (or self-administered), with the aim to cure them, vaccinate them, or alleviate sympt ...
Laboratoires Jacques Logeais between 1960 and 1962. As a hypnotic and sedative, fenadiazole has a unique
oxadiazole Oxadiazoles are a class of heterocyclic aromatic chemical compound of the azole family; with the molecular formula C2H2N2O. There are four isomers of oxadiazole: File:1,2,3-oxadiazole.svg, 1,2,3-oxadiazole File:1,2,4-oxadiazole.svg, 1,2,4-oxadiazo ...
-based
chemical structure A chemical structure determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target molecule or other solid. Molecular geometry refers to the spatial arrangement of ...
. It may be chemically related to certain other hypnotics and sedatives with atypical chemical structures.


References

Drugs with unknown mechanisms of action Hypnotics Oxadiazoles Phenols Sedatives {{Sedative-stub