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...

General Information

Structure

Molecular Formula

C₈H₇N₃O₅

Molecular Mass

225.15828

Exact Mass

225.03857034

Charge

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

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.8699244

LogD (pH = 7.4)

0.8699244

Log P

0.8699244

Molar Refractivity

50.081

Polarizability

18.65204

Polar Surface Area

98.18

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.15

LOG S

-2.79

Solubility (Water)

3.64e-01 g/l

Data Source

Names and Identifiers

Synonyms

3-(5-硝基呋喃甲叉氨基)-2-噁唑烷酮Furazolidone呋喃唑酮FurazolidoneNitrofurazolidonumUSAF EA-1Nitrofurazolidone3-[[(5-Nitro-2-furanyl)methylene]-amino]-2-oxazolidinoneMedaronN-(5-nitro-2-furfurylidene)-3-amino-2-oxazolidoneFuroxane3-(5-nitrofurfurylideneamino)-2-oxazolidinoneTopazoneFurovagFuroxoneNeftinNifulidoneGiarlam3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinone3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinoneDiafuronRoptazolFuraxonFurazolidonTikofuranGiardilTrifuroxFurazolOrtazolPuradin3-{[(5-nitrofuran-2-yl)methylidene]amino}-1,3-oxazolidin-2-one3-(5-nitrofurfurylideneamino)-2-oxazolidinone

IUPAC Traditional name

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

IUPAC name

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

Brand Name

TricoronSclaventerolEnterotoxonFurazonNifurazolidoneOptazolOrtazolFurazolidonFiurox aerosol powderGiarlamViofuragynFuroxanePuradinFuridonMedaronFurallFurazolidineFurozolidineNeftinDiafuronTopazoneFuraxoneNicolenTrichofuronFuraxonCoriziumFuroxNitrofuroxonTikofuranNifulidoneFuroxone Swine MixFurazolBifuronTricofuronFuroxone LiquidNifuranFuroxalFurovagFuroxoneRoptazolFuroxonCoryziumGiardilTrifurox

Names and Identifiers

Registration numbers

CAS Number

67-45-8

PubChem CID

53237143435

PubChem SID

465072912487002416096395924894997

EC Number

MDL Number

KEGG ID

Chemspider ID

CHEMBL

ATC CODE

Wikipedia Title

Unique Ingredient Identifier

5J9CPU3RE0

DrugBank ID

DB00614

Beilstein Number

8317414

Registration numbers

Properties

Pharmacology Properties

Admin Routes

Oral-Local

Mechanism of Action

Interferes with several bacterial Enzyme systems

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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

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

TRC

F864100

Antimicrobial.

Molecule Details

References

PubChem Literature

From Data Sources

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

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

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NGG500

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

• 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)

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

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

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

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

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

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

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

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

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 514

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

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

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

IUPAC name

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

Brand Name

Registration numbers

CAS Number

67-45-8

PubChem CID

53237143435

PubChem SID

465072912487002416096395924894997

EC Number

MDL Number

KEGG ID

Chemspider ID

CHEMBL

ATC CODE

Wikipedia Title

Unique Ingredient Identifier

DrugBank ID

Beilstein Number

Molecule Details

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

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

TRC

F864100

Antimicrobial.

References

PubChem Literature

From Data Sources

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

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

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, NGG500

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

• 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)

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

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

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

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

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

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

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

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

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 514

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

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Admin Routes

Oral-Local

Mechanism of Action

Interferes with several bacterial Enzyme systems

Molecule

ID:496