Nifuratel Chemical Properties

Melting point:

176-178°C

Boiling point:

423.6±53.0 °C(Predicted)

Density 

1.57±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Acetone (Sparingly), DMSO (Slightly)

pka

-2.49±0.40(Predicted)

form 

Solid

color 

Yellow

Stability:

Hygroscopic

CAS DataBase Reference

4936-47-4(CAS DataBase Reference)

Safety Information

Risk Statements 

68

Safety Statements 

36/37

HS Code 

29321900

Toxicity

LD50 oral in mouse: > 4500mg/kg

Nifuratel Usage And Synthesis

Description

Nifuratel is a derivative of nitrofuran , it is a broad spectrum antibiotic with broad-spectrum antimicrobial effect, Nystatin is a polyene antifungal,it has strong effects on trichomoniasis, bacteria, Candida albicans , it plays a strong killing role especially in common pathogens for gynecological infections such as gram-positive and gram-negative bacteria, trichomoniasis, mold, chlamydia and mycoplasma.

Chemical Properties

Bright Yellow Powder.
It is poorly soluble in water, but readily soluble in dimethylformamide.

Originator

Macmiror,Poli,Italy,1965

Uses

Nifuratel is a drug used as an antibacterial, antifungal, antiprotozoal (Trichomonas).
Nifuratel has a broad antibacterial spectrum of action and is effective against Chlamydia trachomatis and Mycoplasma spp. as well as fungal infections from Candida spp.

Definition

ChEBI: Nifuratel is a member of furans and a C-nitro compound.

brand name

Macmiror (Polichimica Sap, Italy); Magmilor (Polichimica Sap, Italy); Polmiror (Polichimica Sap, Italy); Tydantil (Polichimica Sap, Italy).

Mechanism of action

Nifuratel inhibited the IL-6-induced activation of the STAT3 signaling pathway and thereby induced apoptosis and reduced the growth of human gastric cancer cells. Study showed that nifuratel can reduce the viability of gastric cancer cells and stimulate apoptosis in human gastric cancer cells in a dose-dependent manner. In addition, nifuratel induced the arrest of gastric cancer cells in the G2/M phase of the cell cycle. Western blot analysis results suggest that the antitumor activity of nifuratel might be mediated via the STAT3 inhibition. Furthermore, nifuratel can block the IL-6-induced activation of the STAT3 signaling pathway, thereby inhibiting the proliferation of tumor cells. The treatment with nifuratel can upregulate the expression of the proapoptotic protein Bax and downregulate the expression of the antiapoptotic protein Bcl-2[1].

Clinical Use

Nifuratel indications include:
1.bacterial vaginosis, trichomonas vaginitis, vulvovaginal candidiasis, vaginal mixed infections.
2.urinary tract infections.
3.gastrointestinal amoebiasis and trichomoniasis Jia.

Side effects

GI disturbances; peripheral neuropathy; thrombocytopenic purpura; haemolytic anaemia in patients with G6PD deficiency; hypersensitivity reactions; contact dermatitis; hepatotoxicity; blood dyscrasias; pulmonary reactions.

Synthesis

The synthesis of Nifuratel is as follows:Add 450ml of ethanol, 450ml of water, and 50ml of phosphoric acid into the reaction flask, then add 5-nitrofuraldehyde diacetate 267.5 (1.1mol), reflux for 0.5-1h, and naturally cool to room temperature to obtain a 5-nitrofurfural solution. Under dark conditions, add N-amino-5-methylthiomethyl-2-oxazolidinone dropwise to the 5-nitrofurfural solution, stir and react at room temperature for 2 to 3 hours, stand still for crystallization, filter and filtered cake was washed with absolute ethanol solvent (60ml×3) and dried to obtain crude nifuratel. Under dark conditions, take the crude Nifuratel and add 10 times the volume of glacial acetic acid, heat to boil, add activated carbon, filter while hot, the filtrate is allowed to stand for crystallization and filtration, the filter cake is washed with ethanol (60ml×3), nifuratel pure product (197.7g, yield 99.93%, purity 99.93%).

References

[1] Zheng, Hailun , et al. "Nifuratel, a novel STAT3 inhibitor with potent activity against human gastric cancer cells." Cancer Management & Research 9(2017):565-572.

Nifuratel(4936-47-4)Related Product Information

• Nifuratel Impurity 4
• Nifuratel Impurity
• 1-hydrazino-3-(methylthio)propan-2-ol
• 1-METHYLTHIO-2,3-EPOXYPROPANE
• 2-Furoic acid
• Furazolidone
• Methyl carbazate
• 3-AMINO-2-OXAZOLIDINONE
• 2-NITROFURAN
• Nifuratel
• 2-Oxazolidone
• Ethyl carbazate
• 5-Methyloxazolidin-2-one
• 5-NITRO-2-METHYLFURAN
• 2-FURALDEHYDE DIMETHYLHYDRAZONE
• hydrazinecarboxylic acid
• Furmethoxadon
• N-n-propyl-N-formylhydrazine