3-{[(5-nitrofuran-2-yl)methylidene]amino}-1,3-oxazolidin-2-one

• ChemBase ID: 496
• Molecular Formular: C8H7N3O5
• Molecular Mass: 225.15828
• Monoisotopic Mass: 225.03857034
• SMILES: O1CCN(/N=C/c2oc([N+](=O)[O-])cc2)C1=O
• Canonical SMILES: O=C1OCCN1/N=C/c1ccc(o1)[N+](=O)[O-]
• InChI: InChI=1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2
• InChIKey: PLHJDBGFXBMTGZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(5-nitrofuran-2-yl)methylidene]amino}-1,3-oxazolidin-2-one; 3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one
• IUPAC Traditional name: furazolidone; 3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one; furazolum
• Brand Name: Bifuron; Corizium; Coryzium; Diafuron; Enterotoxon; Fiurox aerosol powder; Furall; Furaxon; Furaxone; Furazol; Furazolidine; Furazolidon; Furazon; Furidon; Furovag; Furox; Furoxal; Furoxane; Furoxon; Furoxone; Furoxone Liquid; Furoxone Swine Mix; Furozolidine; Giardil; Giarlam; Medaron; Neftin; Nicolen; Nifulidone; Nifuran; Nifurazolidone; Nitrofuroxon; Optazol; Ortazol; Puradin; Roptazol; Sclaventerol; Tikofuran; Topazone; Trichofuron; Tricofuron; Tricoron; Trifurox; Viofuragyn
• Synonyms: 3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinone; 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinone; Diafuron; Furaxon; Furazol; Furazolidon; Giardil; Giarlam; Ortazol; Puradin; Roptazol; Tikofuran; Trifurox; 3-{[(5-nitrofuran-2-yl)methylidene]amino}-1,3-oxazolidin-2-one; Nitrofurazolidone; Nitrofurazolidonum; USAF EA-1; Furazolidone; Furoxone; Nifulidone; Neftin; 3-(5-nitrofurfurylideneamino)-2-oxazolidinone; 3-[[(5-Nitro-2-furanyl)methylene]-amino]-2-oxazolidinone; 3-(5-nitrofurfurylideneamino)-2-oxazolidinone; N-(5-nitro-2-furfurylidene)-3-amino-2-oxazolidone; Furovag; Furoxane; Medaron; Topazone; Furazolidone; 3-(5-硝基呋喃甲叉氨基)-2-噁唑烷酮; 呋喃唑酮

Database IDs

• CAS Number: 67-45-8
• EC Number: 200-653-3
• MDL Number: MFCD00010550
• Beilstein Number: 8317414
• PubChem SID: 46507291; 24870024; 24894997; 160963959
• PubChem CID: 5323714; 3435
• ATC CODE: QJ01XE90; G01AX06
• CHEMBL: 1103
• Chemspider ID: 3317
• DrugBank ID: DB00614
• KEGG ID: C07999
• Unique Ingredient Identifier: 5J9CPU3RE0
• Wikipedia Title: Furazolidone

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.8699244
• LogD (pH = 7.4): 0.8699244
• Log P: 0.8699244
• Molar Refractivity: 50.081 cm^3
• Polarizability: 18.65204 Å^3
• Polar Surface Area: 98.18 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.15
• LOG S: -2.79
• Solubility (Water): 3.64e-01 g/l

PROPERTIES

Physical Property

• Solubility: 40 mg/L; DMSO
• Apperance: Yellow Solid
• Melting Point: 247-249°C; 254 - 256°C (dec.); 254-256°C dec.
• Hydrophobicity(logP): -0.038; 0.9

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C), Protect from light
• Storage Warning: Light Sensitive
• RTECS: RQ3675000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 62; 68
• Safety Statements: 36; 36/37
• TSCA Listed: 是
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H341-H303; H361
• GHS Precautionary statements: P281; P281-P201-P312-P308+P313-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Admin Routes: Oral-Local
• Mechanism of Action: Interferes with several bacterial Enzyme systems

Product Information

• Purity: 95%; 97%; 98%
• Grade: VETRANAL™, analytical standard
• Application(s): .; Activity against: Escherichia coli; Staphylococcus; Proteus; Giardia lamblia.; Enterobacter aerogenes; Antiseptic, antiprotozoal and antibacterial agent
• Empirical Formula (Hill Notation): C8H7N3O5

DETAILS

MP Biomedicals - 02193465

Crystalline

DrugBank - DB00614

• Drug Groups: approved
• Description: A nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone binds bacterial DNA which leads to the gradual inhibition of monoamine oxidase. (From Martindale, The Extra Pharmacopoeia, 30th ed, p514)
• Indication: For the specific and symptomatic treatment of bacterial or protozoal diarrhea and enteritis caused by susceptible organisms.
• Pharmacology: Furoxone has a broad antibacterial spectrum covering the majority of gastrointestinal tract pathogens including E. coli, staphylococci, Salmonella, Shigella, Proteus, Aerobacter aerogenes, Vibrio cholerae and Giardia lamblia. Its bactericidal activity is based upon its interference with DNA replication and protein production; this antimicrobial action minimizes the development of resistant organisms.
• Toxicity: Reactions to Furoxone have been reported including a fall in blood pressure, urticaria, fever, arthralgia, and a vesicular morbilliform rash. Other adverse effects can include a brown discoloration of the urine; hemolysis can occur in G6PDH-deficient patients. The drug has a monoamine oxidase (MAO) inhibitory effect and should never be given concurrently to individuals already taking MAO inhibitors.
• Affected Organisms: Microbes (bacteria, parasites)
• Biotransformation: Furazolidone is rapidly and extensively metabolized; the primary metabolic pathway identified begins with nitro-reduction to the aminofuran derivative. Two major metabolites are produced: 3-amino-2-oxazolidone (AOZ) or beta-hydroxyethylhydrazine (HEH). AOZ is responsible for monoamine oxidase inhibition. Detoxification and elimination of the drug is done primarily by conjugation with glutathione.
• Absorption: Radiolabeled drug studies indicate that furazolidone is well absorbed following oral administration
• Half Life: 10 minutes
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - F9505

Application
Furazolidone is a nitrofuran derivative with antiprotozoal and antibacterial activity. Furazolidone binds bacterial DNA, which leads to the gradual inhibition of monoamine oxidase. It is used to treat anorexia and antagonism of thiamin utilization in poultry1. Furazolidone increases thapsigargin-sensitive Ca2+-ATPase in chick cardiac myocytes2.
Biochem/physiol Actions
Furazolidone and its generated free radicals, may bind to DNA and induce cross-links. Bacterial DNA is particularly susceptible to this drug, which results in high levels of mutations (transitions and transversions) in the bacterial chromosome. Its mechanism of action minimizes the development of resistant organisms. Furazolidone is a monoamine oxidase (MAO) inhibitor. It increases thapsigargin-sensitive Ca2+-ATPase in chick cardiac myocytes2.
Furazolidone is a monoamine oxidase (MAO) inhibitor and is used as a DNA interstrand cross-linking agent.

Sigma Aldrich - 46297

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - F864100

Antimicrobial.

REFERENCES

• Yurchenco, J.A., et al.: Antimicrob. Chemother., 3, 1035 (1953)
• Sharma, C., et al.: J. Clin. Microbiol., 36, 756 (1953)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 40B, (nmr)
• Yurchenco, J.A. et al., Antibiot. Chemother. (Washington, D.C.), 1953, 3, 1035, (pharmacol)
• Gever, G. et al., J.A.C.S., 1955, 77, 2277; 2282, (synth)
• Rogers, G.S. et al., Antibiot. Chemother. (Washington, D.C.), 1956, 6, 231, (pharmacol)
• Chamberlain, R.E., J. Antimicrob. Chemother., 1976, 2, 325, (rev)
• Cohen, S.M., Carcinog. - Compr. Surv., (ed. Bryan, G.T.), Raven Press, N.Y., 1978, 171-231, (tox)
• Tatsumi, K. et al., Chem. Pharm. Bull., 1982, 30, 3435, (metab, tox)
• IARC Monog., 1983, 31, 141; Suppl. 7, 63, (rev, tox)
• Ali, B.H., Vet. Res. Commun., 1983, 6, 1, (rev, pharmacol)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 837, (synonyms)
• Ali, B.H., Gen. Pharmacol., 1989, 20, 557, (rev)
• Vroomen, L.H.M. et al., Drug Metab. Rev., 1990, 22, 663
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 514
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NGG500