Nifuratel

Names

[ Name ]:
Nifuratel

[Synonym ]:
5-[(Methylthio)methyl]-3-[(5-nitrofurfurylidene)amino]-2-oxazolidinone
Polmiror
UNII:U60U6P08SP
nf113
EINECS 225-576-2
5-[(Methylsulfanyl)methyl]-3-{(E)-[(5-nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one
Magmilor
5-(methylthiomethyl)-3-((5-nitrofuran-2-yl)methyleneamino)oxazolidin-2-one
Nifuratel
Methylmercadone
Tydantil
2-Oxazolidinone, 5-((methylthio)methyl)-3-(((5-nitro-2-furanyl)methylene)amino)-
Macmiror
Omnes
MFCD00057257
sap113
5-(Methylmercaptomethyl)-3-(5-nitro-2-furfurylideneamino)-2-oxazolidinone
5-[(Methylthio)methyl]-3-[[(5-nitro-2-furanyl)methylene]amino]-2-oxazolidinone
Inimur
2-Oxazolidinone, 5-[(methylthio)methyl]-3-[[(1E)-(5-nitro-2-furanyl)methylene]amino]-
5-((Methylthio)methyl)-3-((5-nitrofurfurylidene)amino)-2-oxazolidinone
5-[(Methylsulfanyl)methyl]-3-{[(E)-(5-nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one

Biological Activity

[Description]:

Nifuratel(NF 113, SAP 113) is a broad antibacterial spectrum agent, which is used as an antibacterial, antifungal, and antiprotozoal (Trichomonas).IC50 Value: 0.125-1 μg/mL(MIC, A. vaginae) [1]Target: Antibacterial; Antiprotozoal in vitro: In vitro, nifuratel is able to inhibit the growth of A. vaginae, with a MIC range of 0.125-1 μg/mL; it is active against G. vaginalis and does not affect lactobacilli [1].in vivo: Patients were randomized to receive a 2-week course of bismuth subcitrate (8 mg/kg/day, q.d.s.), amoxicillin (50 mg/kg/day, q.d.s.), with either nifuratel (15 mg/kg/day, q.d.s.) or furazolidone (10 mg/kg/day, q.d.s.), plus omeprazole (0.5 mg/kg, once daily) [2].Toxicity: There were no serious adverse reactions and were no withdrawals due to any side-effects. All of side-effects were self-limiting (dark stools, urine discoloration, blackening of the tongue, and others) [3].Clinical trial: N/A

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Signaling Pathways >> Anti-infection >> Parasite

Natural Products >> Alkaloid

Research Areas >> Infection

[References]

[1]. Polatti F. Bacterial vaginosis, Atopobium vaginae and nifuratel. Curr Clin Pharmacol. 2012 Feb 1;7(1):36-40.

[2]. Nijevitch AA, et al. Helicobacter pylori eradication in childhood after failure of initial treatment: advantage of quadruple therapy withnifuratel to furazolidone. Aliment Pharmacol Ther. 2005 Nov 1;22(9):881-7.

[3]. Nijevitch AA, et al. Nifuratel-containing initial anti-Helicobacter pylori triple therapy in children. Helicobacter. 2007 Apr;12(2):132-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
423.6±53.0 °C at 760 mmHg

[ Melting Point ]:
176-178°C

[ Molecular Formula ]:
C₁₀H₁₁N₃O₅S

[ Molecular Weight ]:
285.276

[ Flash Point ]:
210.0±30.9 °C

[ Exact Mass ]:
285.041931

[ PSA ]:
126.16000

[ LogP ]:
0.27

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.666

[ Storage condition ]:
-20°C Freezer

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RQ3590000

CHEMICAL NAME :: 2-Oxazolidinone, 5-((methylthio)methyl)-3-((5-nitrofurfurylidine)amino )-

CAS REGISTRY NUMBER :: 4936-47-4

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C10-H11-N3-O5-S

MOLECULAR WEIGHT :: 285.30

WISWESSER LINE NOTATION :: T5OJ BNW E1UN- AT5NVOTJ E1S1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 50 ng/plate

REFERENCE :: MIGIA6 Minerva Ginecologia. (Edizioni Minerva Medica, Casella Postale 491, I-10126 Turin, Italy) V.1- 1949- Volume(issue)/page/year: 31,263,1979

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin .

[ Safety Phrases ]:
S26-S36-S37/39

[ WGK Germany ]:
3