| Identification | More | [Name]
Nifuratel | [CAS]
4936-47-4 | [Synonyms]
5-[(METHYLTHIO)METHYL]-3-[[(5-NITRO-2-FURANYL)METHYLENE]AMINO-]-2-OXAZO-LIDINONE
5-methylthiomethyl-3-(5-nitrofurfurylideneamino)-2-oxazolidone
MACMIROR
NIFURATEL
5-((methylthio)methyl)-3-((5-nitrofurfurylidine)amino)-2-oxazolidinon
5-((methylthio)methyl)-3-((5-nitrofurfurylidine)amino)-2-oxazolidinone
l’n-(5-nitro-2-furfurilidene)-3-amino-5-metilmercaptometil-2-ossazolidinone
magmilor
methylmercadone
nf113
omnes
polmiror
sap113
NIFURATEL (MACMIROR)
5-[(Methylthio)methyl]-3-[[(5-nitro-2-furanyl)methylene]amino]-2-oxazolidinone, Methylmercadone, Inimur, Macmiror, Magmilor, Omnes, Polmiror, Tydantil
Nifuratel ,98%
Inimur
Tydantil | [EINECS(EC#)]
225-576-2 | [Molecular Formula]
C10H11N3O5S | [MDL Number]
MFCD00057257 | [Molecular Weight]
285.28 | [MOL File]
4936-47-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow Solid | [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 | [Usage]
Used as an antibacterial, antifungal, antiprotozoal (Trichomonas) | [Detection Methods]
HPLC,NMR | [Stability:]
Hygroscopic | [CAS DataBase Reference]
4936-47-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [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]
Yellow Solid | [Originator]
Macmiror,Poli,Italy,1965 | [Uses]
Nifuratel is a drug used as an antibacterial, antifungal, antiprotozoal (Trichomonas). Nifuratel appears to have a broad antibacterial spectrum of action and is effective against Chlamydia trachomatis and Mycoplasma spp. as well as fungal infections from Candida spp.
Nifuratel is an antibacterial, antifungal, and antiprotozoal compound with activity against Trichomonas. | [Definition]
ChEBI: Nifuratel is a member of furans and a C-nitro compound. | [Manufacturing Process]
In an initial step of reactions, methyl mercaptan is reacted with
epichlorohydrin to give 1chloro-3-methylthio-2-propanol. That is reacted with
hydrazine hydrate to give 3-methylmercapto-2-hydroxypropyl hydrazine.
11.8 grams of diethyl carbonate (0.1 mols) and a solution of sodium
methoxide prepared from 0.12 gram of sodium in 4 cc of anhydrous methanol,
were added to 13.2 grams of 3-methylmercapto-2-hydroxypropyl hydrazine.
After the reaction vessel had been fitted with a Liebig condenser, the reaction
mixture was heated by means of an oil bath which was gradually heated up to
110°C, to remove first methyl alcohol and then ethyl alcohol formed during
the reaction. After about two-thirds of the theoretical amount of ethyl alcohol
had been distilled off, the heating was discontinued and the reaction mixture
was diluted with 50 cc of ethyl alcohol and poured into a 5-nitro-2-
furfuraldehyde solution prepared by boiling for 30 minutes 0.1 mol of
nitrofurfuraldehyde diacetate in 100 ml of ethyl alcohol and 50 ml of 1:10
sulfuric acid.
A yellow crystalline precipitate was immediately formed, which, after
crystallization from acetic acid, melted at 182°C and consisted of N-(5-nitro-
2-furfurylidene)-3-amino-5-methyl-mercaptomethyl-2-oxazolidinone. | [Brand name]
Macmiror (Polichimica Sap, Italy); Magmilor
(Polichimica Sap, Italy); Polmiror (Polichimica Sap,
Italy); Tydantil (Polichimica Sap, Italy). | [Therapeutic Function]
Vaginal antiinfective | [Pharmaceutical Applications]
A synthetic compound available as tablets and vaginal preparations.
It is poorly soluble in water, but readily soluble in
dimethylformamide.
The activity is similar to that of nitrofurantoin but it is
more active, especially against Gram-negative anaerobes.
It also has modest, but clinically useful, activity against
Candida albicans. Little is known about the pharmacokinetics.
It structurally resembles furazolidone, and may
undergo a similar degree of metabolism. It does not achieve
therapeutic concentrations in the bloodstream after oral
administration and it seems likely that the antibacterial
activity in urine is due to active metabolites. There is little
or no systemic absorption when vaginal suppositories are
used.
As with other members of the group, side effects are mostly
associated with the upper gastrointestinal tract. It is used to
treat urinary infections and vaginal candidiasis. | [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%).
 | [storage]
Store at -20°C | [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. |
|
|