Furonazide

Furonazide is a crystalline tuberculostatic drug substance with a reported melting point of 199-201.5 °C.[1]

Furonazide
Names
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)
ChEBI
ChemSpider
ECHA InfoCard 100.020.375
EC Number
  • 222-411-6
UNII
  • InChI=1S/C12H11N3O2/c1-9(11-3-2-8-17-11)14-15-12(16)10-4-6-13-7-5-10/h2-8H,1H3,(H,15,16)/b14-9-
    Key: GNDPAVKYAUIVEB-ZROIWOOFSA-N
  • C/C(=N/NC(=O)c1ccncc1)/c2ccco2
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).
Infobox references

Synthesis

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

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
  1. Kazuo Miyatake, “Derivatives of isonicotinic acid hydrazide”, Japanese Patent 32,002,484 B4 (1957)
  2. 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.
  3. 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.
  4. 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.
  5. "Drugs - Synonyms and Properties" data were obtained from Ashgate Publishing Co. (US)
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