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Names | |
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Preferred IUPAC name
N′-[1-(Furan-2-yl)ethylidene]pyridine-4-carbohydrazide | |
Other names
4-Pyridinecarboxylic acid [1-(2-furanyl)ethylidene]hydrazide
Furilazone Clitizina Menazone FKI | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.020.375 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C12H11N3O2 | |
Molar mass | 229.239 g·mol−1 |
Appearance | crystals |
Melting point | 199 to 201.5 °C (390.2 to 394.7 °F; 472.1 to 474.6 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Furonazide is a crystalline tuberculostatic drug substance with a reported melting point of 199-201.5 °C.[1]
Synthesis
[edit]Furonazide was first prepared in 1955 by Miyatake from isoniazid and 2-Acetylfuran by refluxing in ethanol, followed by filtration of the crystalline product.[1][2]
Applications
[edit]Furonazide has shown bacteriostatic action and is tuberculostatic at levels of 10−8 molar.[1] The in vitro antibacterial activity of furonazide against Bacillus Calmette-Guerin was found to be essentially equal to that of isoniazid on an equimolar basis.[3] In vivo studies in the guinea pig showed furonazide slightly more active than isoniazid as a tuberculostatic agent.[4] The drug has relatively low toxicity. The median lethal dose (LD50, rat oral) was reported as 2,600 mg/kg.[5]
References
[edit]- ^ a b c Kazuo Miyatake, “Derivatives of isonicotinic acid hydrazide”, Japanese Patent 32,002,484 B4 (1957)
- ^ Kazuo Miyatake; Ichimura, Shozo; Nagasaki, Senkichi; Hoji, Kazuhiko (1955). "Syntheses of compounds related to isonicotinic acid hydrazide. III. Antitubercular compounds". Yakugaku Zasshi. 75: 1066–9. doi:10.1248/yakushi1947.75.9_1066.
- ^ Kiichiro Kakemi; Sezaki, Hitoshi; Iwamoto, Kikuo; Sano, Yukito (1969). "Stability of drugs in biological media. II. Relations between the stability in culture media and antibacterial activity of some isoniazid derivatives". Chemical & Pharmaceutical Bulletin. 17 (8): 1623–8. doi:10.1248/cpb.17.1623. PMID 4981613.
- ^ Giovanni Pacilio; Pagnini, Pietro; Genazzani, Enrico (1964). "Tuberculostatic activity of some isoniazid derivatives administered to guinea pigs at different time intervals". Atti della Societa Italiana delle Scienze Veterinarie. 18: 631–6.
- ^ "Drugs - Synonyms and Properties" data were obtained from Ashgate Publishing Co. (US)