Furonazide

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
CAS Number	3460-67-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:134941;
ChemSpider	4655810;
ECHA InfoCard	100.020.375
EC Number	222-411-6;
PubChem CID	5338184;
UNII	3OUZ124988;
CompTox Dashboard (EPA)	DTXSID90876716 ;
	InChI 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;
	SMILES C/C(=N/NC(=O)c1ccncc1)/c2ccco2;
Properties
Chemical formula	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

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

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

^ ^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)

[Miyatake-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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