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HomeProduct name listNifuratel

Nifuratel

  • CAS NO.:4936-47-4
  • Empirical Formula: C10H11N3O5S
  • Molecular Weight: 285.28
  • MDL number: MFCD00057257
  • EINECS: 225-576-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 18:15:48
Nifuratel Structural

What is Nifuratel?

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

The Uses of Nifuratel

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.

What are the applications of Application

Nifuratel is an antibacterial, antifungal, and antiprotozoal compound

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%).

4936-47-4.png

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.

Properties of Nifuratel

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)
form  Solid
pka -2.49±0.40(Predicted)
color  Yellow
Stability: Hygroscopic
CAS DataBase Reference 4936-47-4(CAS DataBase Reference)

Safety information for Nifuratel

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P330:Rinse mouth.
P362:Take off contaminated clothing and wash before reuse.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.
P405:Store locked up.
P403+P233:Store in a well-ventilated place. Keep container tightly closed.
P501:Dispose of contents/container to..…

Computed Descriptors for Nifuratel

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