Chemistry:Fenadiazole

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Short description: Chemical compound
Fenadiazole
Fenadiazole.svg
Ball-and-stick model of the fenadiazole 3D ball.png molecule
Clinical data
Trade namesHypnazol, Eudormil, Viodor
Other namesFenadiazol; Fenadiazolum; Fenodiazole; Phénadiazole; Phenadiazole; JL-512; J. L. 512; NSC-100729; 2-(o-Hydroxyphenyl)-1,3,4-oxadiazole; 2-(2-Hydroxyphenyl)-1,3,4-oxadiazole; o-1,3,4-Oxadiazol-2-ylphenol
Routes of
administration		By mouth
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC8H6N2O2
Molar mass162.148 g·mol−1
3D model (JSmol)
  (verify)

Fenadiazole (INN), also known as phénadiazole (DCF)[1] and sold under the brand names Hypnazol, Eudormil, and Viodor, is a hypnotic and sedative medication which has been used to treat insomnia but is no longer marketed.[2][3][4][5][6][7] It is described as a non-barbiturate hypnotic with marked or profound hypnotic and sedative properties in animals, variable hypnotic effects in humans (rapidly inducing sleep for 6 to 8 hours), additional anticonvulsant, antithermal, and spasmolytic effects, and a generally well-tolerated profile in humans (at an average dosage of 200 mg/day).[7][8][9][10] The drug was synthesized, pharmacologically characterized, patented, and marketed by the French pharmaceutical company Laboratoires Jacques Logeais between 1960 and 1962.[2][9][3][6] As a hypnotic and sedative, fenadiazole has a unique oxadiazole-based chemical structure.[11] It may be chemically related to certain other hypnotics and sedatives with atypical chemical structures.[11][7]

References

  1. ↑ Nordisk veterinärmedicin. Nordisk veterinærmedicin. 1949. OCLC 1638883. https://books.google.com/books?id=rbdYAAAAYAAJ. "Fenadiazolum (DCF, pINN). 2-(2-Hydroxyphenyl)-1,3,4-oxadiazol. Fenadiazol. DCF: Phénadiazole R: Hypnazol (Hypnoticum)." 
  2. ↑ 2.0 2.1 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 662–. ISBN 978-1-4757-2085-3. OCLC 1058412474. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA662. "2-(2-Hydroxyphenyl)-1,3,4-oxadiazole H-00192. o-1,3,4-Oxadiazol-2-ylphenol, 8CI. Fenadiazole, INN. Hypnazol. Eudormil. Viodor. JL 512. [1008-65-7]. C8H6N2O2 M 162.148. Hypnotic, sedative. Mp 111-112°. Bp0.1 180°. ▷SM5850000. Maillard, J. et al, Bull. Soc. Chim. Fr., 1961, 529 (synth). Vincent, M. et al, Bull. Soc. Chim. Fr., 1962, 1580 (synth, pharmacol)." 
  3. ↑ 3.0 3.1 The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.). Whitehouse Station, NJ: Merck Research Laboratories. 1996. p. 620. ISBN 978-0-911910-12-4. "3898. Fenadizole. 2-(1,3,4-Oxadiazol-2-yl)phenol; 2-(o-hydroxyphenyl)-1,3,4-oxadiazole; Hypnazol. C8H6N2O2; mol wt 162.14. C 59.26%, H 3.73%, N 17.27%, O 19.74%. Prepn: Maillard et al., Bull. Soc. Chim. France 1961, 529; Vincent et al., ibid. 1962, 1580; Brit. pat. 902,388 and Maillard et al., Fr. pat. M379, C.A. 57, 15251g (1962) (both 1962 to Logeais Labs.). [Chemical structure figure] Crystals from methanol. mp 111–112°. bp0.1 180°. LD50 i.p. in mice: 940 mg/kg. THERAP CAT: Hypnotic." 
  4. ↑ Organic-chemical Drugs and Their Synonyms: An International Survey, Volume 1 (5 ed.). Akademie-Verlag. 1978. p. 130. ISBN 978-0-89573-100-5. OCLC 4208605. https://books.google.com/books?id=8SdtAAAAMAAJ. "2-(o-Hydroxyphenyl)-1,3,4-oxadiazol S Eudormil, Fenadiazol**, Hypnazol, J.L. 512, Phénadiazole, Viodor V Hypnoticum, Sedativum" 
  5. ↑ "Unknown". Journal de médecine de Bordeaux et de la région du sud-ouest ...: Fondé en 1829 138: 1045. 1961. OCLC 49481532. https://books.google.com/books?id=R_MvAQAAMAAJ. "Un somnifère non barbiturique, l'hypnazol. Il s'agit du 2 (O-hydroxy-Phényl-1-3-4-Oxadiazol) préparé par les laboratoires Logeais. Blanc et Blanc-Cuttoli (Lyon méd., 2 juill. 1961, no 27) l'ont essayé chez quarante-quatre personnes âgées placées pour affections diverses à l'infirmerie d'une maison de retraite et qui toutes étaient habituées aux barbituriques. Ceux-ci ont été remplacés par un à deux comprimés d'Hypnazol, pris le soir au dîner ou dans le courant de la nuit. Sur quatorze sujets présentant une insomnie essentielle, c'est-à-dire sans cause pathologique apparente, le résultat fut excellent dans douze cas: le sommeil apparaissant vingt minutes environ après la prise du médicament et durant six à sept heures, le réveil se faisant sans obnubilation ni fatigue. Chez sept malades psychiques, anxieux, deux comprimés ne donnèrent de bons résultats que trois fois. Sur neuf cas de sujets dyspnéiques (cardiaques, emphysemateux, asthmatiques), l'hypnazol (1 comprimé) assccié au traitement de la maladie dypnéisante, les résultats furent excellents dans huit cas, nuls chez un éthylique. Enfin sur un groupe de malades algiques (cancéreux, hémiplégiques, rhumatisants, artéritiques), le somnifère ne donna rien sans antialgiques; mais quand ceux-ci ne procurent pas le sommeil l'adjonction d'hypnazol peut le faire. L'association fut ainsi bienfaisante dans six cas sur quatorze. En définitive, c'est dans l'insomnie essentielle du vieillard ou bien en association avec le traitement des maladies dyspnéisantes, et encore à moindre titre en association avec les antialgiques chez les douloureux, que l'hypnazol trouve Ses meilleures indications. Il n'est pas toxique, permet un réveil agréable. Il n'est que de rares cas où il provoque quelques brûlures d'estomac.". 
  6. ↑ 6.0 6.1 Society of Chemical Industry (Great Britain) (1960). Reports on the Progress of Applied Chemistry. Society of Chemical Industry. OCLC 1765911. https://books.google.com/books?id=4DYPAAAAMAAJ. "Yet another new type of compound, 2-o-hydroxy-1,3,4-oxadiazole (Hypnazol) has hypnotic properties and has been used successfully in the treatment of insomnia (8)." 
  7. ↑ 7.0 7.1 7.2 Les hypnotiques. Presses universitaires de France. 1963. OCLC 14552633. https://books.google.com/books?id=f_IYAAAAIAAJ. "Les hypnotiques suivants sont des substances diazotées, c'est-à-dire qu'elles renferment 2 N dans leur constitution: L'hypnazole: soporifique modérateur de l'activité spontanée, anticonvulsivant, antithermique et spasmolytique; Le révonal, dérivé de la quinazolinone, possède expérimentalement une activité hypnotique, analgésique, anti-inflammatoire et antipyrétique." 
  8. ↑ Maillard J, Vincent M, Morin R, Benard M, "Hypnotic and sedative drug, 2-(o-hydroxyphenyl)-1,3,4-oxadiazole.", FR patent 379, issued 8 January 1962, assigned to Societe d'Exploitation des Laboratoires Jacques Logeais. 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.
  9. ↑ 9.0 9.1 "Derivatives of 1,3,4-oxadiazole" GB patent 902388, issued 1 August 1962, assigned to Societe d'Exploitation des Laboratoires Jacques Logeais 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.
  10. ↑ "A new nonbarbiturate hypnotic, 2-(o-hydroxyphenyl)-1,3,4-oxadiazole.". Revue Médicale de Nancy 85: 413–418. 1960. "Abstract: Tests of this compd. (JL 512) in rats indicated a low toxicity. Profound sleep was induced without preliminary excitation. The compd. also showed some anticonvulsant action, and had no adverse side effects on the blood or kidneys even after prolonged administration. In 111 trials on 83 patients with various diseases, at av. doses of 0.2 g./day, the hypnotic effects were variable although the compd. was generally well-tolerated.". 
  11. ↑ 11.0 11.1 "3.3 Hypnotics and Sedatives Not Belonging to the Classes of Barbiturates and Benzodiazepines". Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists. Walter de Gruyter. 31 December 1997. pp. 399–426. doi:10.1515/9783110881615.399. ISBN 978-3-11-010731-9. OCLC 1091453690. https://books.google.com/books?id=ZhYtynyC4kAC&pg=PA421. "2-(l,3,4-Oxadiazol-2-yl)phenol, 2-(o-hydroxyphenyl)-l,3,4-oxadiazole, Fenadiazole, Hypnazole (Hypnotic). [...] Other compounds used as hypnotics or sedatives are tribromomethane (bromoform), hydrobromic acid, phenyl-methyl-ketone (acetophenone), the imidazole derivative Etomidate, the oxadiazole derivative Fenodiazole (Hypnazole) and the sulfones Sulfonal (Sulfomethane) and Ethylsulfonal (Trional) (table 9)." 





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