Nifuroxazide Chemical Properties

Melting point:

281-283°C

Boiling point:

418.17°C (rough estimate)

Density 

1.3877 (rough estimate)

refractive index 

1.5700 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Practically insoluble in water, slightly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.

pka

8.36±0.15(Predicted)

color 

Yellow

BRN 

4264976

CAS DataBase Reference

965-52-6(CAS DataBase Reference)

Safety Information

WGK Germany 

3

RTECS 

DH2528300

Toxicity

LD50 intraperitoneal in mouse: 1gm/kg

MSDS

• Language:English Provider:Nifuroxazide
• Language:English Provider:SigmaAldrich

Nifuroxazide Usage And Synthesis

Chemical Properties

Yellow Solid

Originator

Ercefuryl,Carriere,France,1964

Uses

Nifuroxazide is an intestinal antiseptic. Nifuroxazide, is still used as a veterinary drug illegally in some countries. SEE H829102 as a test for antibiotic in broiler chickens.

Definition

Nifuroxazide is a member of benzoic acids. Nifuroxazide is an oral nitrofuran antibiotic used to treat mild diarrhea in humans and animals.

Manufacturing Process

13 g (0.1 mol) of 4-hydroxybenzhydrazide were dissolved in a boiling mixture of 100 ml of water and an equal volume of dimethylformamide. 15.5 g (0.11 mol) of 5-nitrofurfural dissolved in 31 ml of dimethylformamide were added to this hot solution, and the mixture was stirred and brought to the boiling point.
The mixture was then allowed to stand for fifteen hours. The precipitate was separated, washed twice with 100 ml of water, and recrystallized by dissolving it in 250 ml of hot pyridine and pouring this solution into 250 ml of water.
The 5-nitrofurfurylidene hydrazide of 4-hydroxybenzoic acid obtained was washed with water and methanol and was dried at a moderate temperature. It weighed 23 g (83.7% yield), and melted at 298°C. The percentage nitrogen determined by the micro-Dumas method was 15.41% (theory 15.27%).

Therapeutic Function

Antiseptic

Biological Activity

Nifuroxazide is a nitrofuran antibiotic. It is active against strains of the enteropathogenic bacteria C. jejuni, Salmonella, Y. enterocolitica, Shigella, and E. coli. It inhibits quorum sensing and virulence factor production in P. aeruginosa. Nifuroxazide inhibits STAT3 activity in a reporter assay (IC50 = ~3 μM) and decreases viability of U266 and INA-6 myeloma cells, which have constitutive STAT3 phosphorylation, with EC50 values of approximately 4.5 μM for both. It also decreases viability, migration, and invasion of, and induces apoptosis in, MCF-7, 4T1, and MDA-MB-231 breast cancer cells. Nifuroxazide (50 mg/kg per day) reduces tumor growth and prevents pulmonary metastasis in a 4T1 murine mammary carcinoma model. It also reduces diarrhea, weight loss, and colon inflammation in a rat model of acetic acid-induced ulcerative colitis.

Nifuroxazide(965-52-6)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Nifuratel
• 1,5-Diphenylcarbazide
• Formylhydrazine
• DIPHENYLCARBAZONE
• 4-Nitrobenzonitrile
• Decanedihydrazide
• Glycine
• Carbohydrazide
• Adipic dihydrazide
• Tebufenozide
• Folic acid
• METHOXYFENOZIDE
• Thiamine nitrate
• antioxidant 1024
• 4-Hydroxybenzhydrazide
• nihydrazone
• 4-HYDROXY-BENZYL-HYDRAZINE