CAS 67-45-8|Furazolidone|furazolum|3-(5-硝基呋喃甲叉氨基)-2-噁唑烷酮|呋喃唑酮|3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one|Tricoron|Bifuron|Nitrofurazolidonum|Tricofuron|Furoxo...

基本信息

化学结构

分子式

C₈H₇N₃O₅

分子量

225.15828

精确质量

225.03857034

电荷

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

Canonic Smiles

O=C1OCCN1/N=C/c1ccc(o1)[N+](=O)[O-]

Isomeric Smiles

O1CCN(/N=C/c2oc([N+](=O)[O-])cc2)C1=O

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

0.8699244

LogD (pH = 7.4)

0.8699244

Log P

0.8699244

摩尔折射率

50.081

极化性

18.65204

极化表面积

98.18

可自由旋转的化学键

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

数据来源

名称和标识

别名

Furazolidone3-(5-硝基呋喃甲叉氨基)-2-噁唑烷酮呋喃唑酮NitrofurazolidonumNitrofurazolidoneUSAF EA-1FurazolidoneFuroxaneFurovag3-[[(5-Nitro-2-furanyl)methylene]-amino]-2-oxazolidinoneMedaronN-(5-nitro-2-furfurylidene)-3-amino-2-oxazolidone3-(5-nitrofurfurylideneamino)-2-oxazolidinoneTopazoneNeftinNifulidoneFuroxone3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinoneDiafuronFurazolidonGiarlamTikofuran3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinoneRoptazolFuraxonPuradinTrifuroxGiardilOrtazolFurazol3-{[(5-nitrofuran-2-yl)methylidene]amino}-1,3-oxazolidin-2-one3-(5-nitrofurfurylideneamino)-2-oxazolidinone

IUPAC传统名

furazolum furazolidone 3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one

IUPAC标准名

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

商标名

TricoronBifuronTricofuronFuroxone LiquidNifurazolidoneTrifuroxFiurox aerosol powderSclaventerolFuroxoneEnterotoxonFuraxoneFuroxonGiardilNitrofuroxonPuradinNifulidoneFuroxaneFuroxone Swine MixFurozolidineFuridonTrichofuronFurallFurovagCoryziumFurazolidineViofuragynNifuranOrtazolDiafuronTopazoneMedaronCoriziumFuroxTikofuranFurazonFurazolidonNeftinFurazolGiarlamRoptazolFuraxonFuroxalNicolenOptazol

名称和标识

数据登录号

CAS号

67-45-8

PubChem CID

53237143435

PubChem SID

465072912487002416096395924894997

EC号

MDL号

KEGG ID

Chemspider ID

CHEMBL

ATC码

维基百科标题

美国药典/FDA物质标识码

DrugBank ID

Beilstein号

数据登录号

化合物性质

药理学性质

给药途径

Oral-Local

生物活性机理

Interferes with several bacterial Enzyme systems

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

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]

Crystalline

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.

46297

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

TRC

F864100

Antimicrobial.

描述信息

参考文献

PubChem文献

数据源提供

• Sharma, C., et al.: J. Clin. Microbiol., 36, 756 (1953)

• Yurchenco, J.A., et al.: Antimicrob. Chemother., 3, 1035 (1953)

• Yurchenco, J.A. et al., Antibiot. Chemother. (Washington, D.C.), 1953, 3, 1035, (pharmacol)

• Rogers, G.S. et al., Antibiot. Chemother. (Washington, D.C.), 1956, 6, 231, (pharmacol)

• Vroomen, L.H.M. et al., Drug Metab. Rev., 1990, 22, 663

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 40B, (nmr)

• Tatsumi, K. et al., Chem. Pharm. Bull., 1982, 30, 3435, (metab, tox)

• Ali, B.H., Vet. Res. Commun., 1983, 6, 1, (rev, pharmacol)

• Gever, G. et al., J.A.C.S., 1955, 77, 2277; 2282, (synth)

• Cohen, S.M., Carcinog. - Compr. Surv., (ed. Bryan, G.T.), Raven Press, N.Y., 1978, 171-231, (tox)

• IARC Monog., 1983, 31, 141; Suppl. 7, 63, (rev, tox)

• 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

• Chamberlain, R.E., J. Antimicrob. Chemother., 1976, 2, 325, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 837, (synonyms)

• Ali, B.H., Gen. Pharmacol., 1989, 20, 557, (rev)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

别名

IUPAC传统名

furazolum furazolidone 3-[(E)-[(5-nitrofuran-2-yl)methylidene]amino]-1,3-oxazolidin-2-one

IUPAC标准名

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

商标名

数据登录号

CAS号

67-45-8

PubChem CID

53237143435

PubChem SID

465072912487002416096395924894997

EC号

MDL号

KEGG ID

Chemspider ID

CHEMBL

ATC码

维基百科标题

美国药典/FDA物质标识码

DrugBank ID

Beilstein号

描述信息

DB00614

Drug Groups

approved

Description

Indication

For the specific and symptomatic treatment of bacterial or protozoal diarrhea and enteritis caused by susceptible organisms.

Pharmacology

Toxicity

Affected Organisms

Microbes (bacteria, parasites)

Biotransformation

Absorption

Radiolabeled drug studies indicate that furazolidone is well absorbed following oral administration

Half Life

10 minutes

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Crystalline

F9505

46297

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

TRC

F864100

Antimicrobial.

参考文献

PubChem文献

数据源提供

• Sharma, C., et al.: J. Clin. Microbiol., 36, 756 (1953)

• Yurchenco, J.A., et al.: Antimicrob. Chemother., 3, 1035 (1953)

• Yurchenco, J.A. et al., Antibiot. Chemother. (Washington, D.C.), 1953, 3, 1035, (pharmacol)

• Rogers, G.S. et al., Antibiot. Chemother. (Washington, D.C.), 1956, 6, 231, (pharmacol)

• Vroomen, L.H.M. et al., Drug Metab. Rev., 1990, 22, 663

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 40B, (nmr)

• Tatsumi, K. et al., Chem. Pharm. Bull., 1982, 30, 3435, (metab, tox)

• Ali, B.H., Vet. Res. Commun., 1983, 6, 1, (rev, pharmacol)

• Gever, G. et al., J.A.C.S., 1955, 77, 2277; 2282, (synth)

• Cohen, S.M., Carcinog. - Compr. Surv., (ed. Bryan, G.T.), Raven Press, N.Y., 1978, 171-231, (tox)

• IARC Monog., 1983, 31, 141; Suppl. 7, 63, (rev, tox)

• 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

• Chamberlain, R.E., J. Antimicrob. Chemother., 1976, 2, 325, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 837, (synonyms)

• Ali, B.H., Gen. Pharmacol., 1989, 20, 557, (rev)

生物活性

PubChem BioAssay

化合物性质

药理学性质

给药途径

Oral-Local

生物活性机理

Interferes with several bacterial Enzyme systems

化合物信息

ID:496