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

• ChemBase编号: 496
• 分子式: C8H7N3O5
• 平均质量: 225.15828
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: furazolidone; 3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one; furazolum
• 商标名: 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
• 别名: 3-(5-硝基呋喃甲叉氨基)-2-噁唑烷酮; 呋喃唑酮; 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

登记号

• CAS号: 67-45-8
• EC号: 200-653-3
• MDL号: MFCD00010550
• Beilstein号: 8317414
• PubChem SID: 46507291; 24870024; 24894997; 160963959
• PubChem CID: 3435; 5323714
• ATC码: G01AX06; QJ01XE90
• CHEMBL: 1103
• Chemspider ID: 3317
• DrugBank ID: DB00614
• KEGG ID: C07999
• 美国药典/FDA物质标识码: 5J9CPU3RE0
• 维基百科标题: Furazolidone

理论计算性质

JChem

• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 0.8699244
• LogD (pH = 7.4): 0.8699244
• Log P: 0.8699244
• 摩尔折射率: 50.081 cm^3
• 极化性: 18.65204 Å^3
• 极化表面积: 98.18 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.15
• LOG S: -2.79
• 溶解度: 3.64e-01 g/l

分子性质

理化性质

• 溶解度: 40 mg/L; DMSO
• 外观: Yellow Solid
• 熔点: 247-249°C; 254 - 256°C (dec.); 254-256°C dec.
• 疏水性(logP): -0.038; 0.9

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C), Protect from light
• 保存注意事项: Light Sensitive
• RTECS编号: RQ3675000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 62; 68
• 安全公开号: 36; 36/37
• TSCA收录: 是
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H341-H303; H361
• GHS警示性声明: P281; P281-P201-P312-P308+P313-P405-P501A
• 个人保护装置: 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

药理学性质

• 给药途径: Oral-Local
• 生物活性机理: Interferes with several bacterial Enzyme systems

产品相关信息

• 纯度: 95%; 97%; 98%
• 级别: VETRANAL™, analytical standard
• 应用领域: .; Activity against: Escherichia coli; Staphylococcus; Proteus; Giardia lamblia.; Enterobacter aerogenes; Antiseptic, antiprotozoal and antibacterial agent
• Empirical Formula (Hill Notation): C8H7N3O5

详细说明

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - F864100

Antimicrobial.

参考文献

• 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