:Furonazide
{{Chembox
| ImageFile = Furonazide.svg
| ImageSize =
| PIN = N′-[1-(Furan-2-yl)ethylidene]pyridine-4-carbohydrazide
| OtherNames = 4-Pyridinecarboxylic acid [1-(2-furanyl)ethylidene]hydrazide
Furilazone
Clitizina
Menazone
FKI
| Section1 = {{Chembox Identifiers
| CASNo = 3460-67-1
| PubChem = 5338184
| ChemSpiderID = 4655810
| ChEBI = 134941
| EC_number = 222-411-6
| UNII = 3OUZ124988
| SMILES = C/C(=N/NC(=O)c1ccncc1)/c2ccco2
| InChI =
| InChIKey =
| StdInChI = 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-
| StdInChIKey = GNDPAVKYAUIVEB-ZROIWOOFSA-N
}}
| Section2 = {{Chembox Properties
| C=12 | H=11 | N=3 | O=2
| Appearance = crystals
| MeltingPtC = 199 to 201.5
| MeltingPt_notes =
| BoilingPt =
| Solubility =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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Furonazide is a crystalline tuberculostatic drug substance with a reported melting point of 199-201.5 °C.Kazuo Miyatake, “Derivatives of isonicotinic acid hydrazide”, Japanese Patent 32,002,484 B4 (1957)
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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.{{cite journal | author = Kazuo Miyatake | title = Syntheses of compounds related to isonicotinic acid hydrazide. III. Antitubercular compounds | journal = Yakugaku Zasshi| volume = 75 | pages =1066–9| year = 1955| last2 = Ichimura | first2 = Shozo |last3 = Nagasaki | first3 = Senkichi | last4 = Hoji | first4 = Kazuhiko|doi=10.1248/yakushi1947.75.9_1066| doi-access = free }}
Applications
Furonazide has shown bacteriostatic action and is tuberculostatic at levels of 10−8 molar. 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.{{cite journal | author = Kiichiro Kakemi | title = Stability of drugs in biological media. II. Relations between the stability in culture media and antibacterial activity of some isoniazid derivatives| journal = Chemical & Pharmaceutical Bulletin| volume = 17| pages =1623–8| year = 1969| last2 = Sezaki| first2 = Hitoshi|last3 = Iwamoto| first3 = Kikuo| last4 = Sano| first4 = Yukito | doi = 10.1248/cpb.17.1623 | issue = 8| pmid = 4981613| doi-access = free}} In vivo studies in the guinea pig showed furonazide slightly more active than isoniazid as a tuberculostatic agent.{{cite journal | author = Giovanni Pacilio| title = Tuberculostatic activity of some isoniazid derivatives administered to guinea pigs at different time intervals| journal = Atti della Societa Italiana delle Scienze Veterinarie| volume = 18 | pages =631–6| year = 1964| last2 = Pagnini| first2 = Pietro|last3 = Genazzani| first3 = Enrico}} The drug has relatively low toxicity. The median lethal dose (LD50, rat oral) was reported as 2,600 mg/kg."Drugs - Synonyms and Properties" data were obtained from Ashgate Publishing Co. (US)