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F9505

Sigma-Aldrich

Furazolidone

Synonym(s):

3-(5-Nitrofurfurylideneamino)-2-oxazolidinone

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About This Item

Empirical Formula (Hill Notation):
C8H7N3O5
CAS Number:
67-45-8
Molecular Weight:
225.16
Beilstein:
8317414
EC Number:
200-653-3
MDL number:
MFCD00010550
UNSPSC Code:
51102829
PubChem Substance ID:
24894997
NACRES:
NA.85

biological source

synthetic

form

powder

color

yellow

mp

256-256 °C

solubility

formic acid: 50 mg/mL

antibiotic activity spectrum

Gram-positive bacteria
parasites

Mode of action

enzyme | inhibits

SMILES string

[O-][N+](=O)c1ccc(\C=N\N2CCOC2=O)o1

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/b9-5+

InChI key

PLHJDBGFXBMTGZ-WEVVVXLNSA-N

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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 poultry. Furazolidone increases thapsigargin-sensitive Ca2+-ATPase in chick cardiac myocytes.

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 and is used as a DNA interstrand cross-linking agent.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nitrofurazone United States Pharmacopeia (USP) Reference Standard

USP

1465004

Nitrofurazone

Flurbiprofen cyclooxygenase inhibitor

Sigma-Aldrich

F8514

Flurbiprofen

Nitrofural impurity B European Pharmacopoeia (EP) Reference Standard

Y0001570

Nitrofural impurity B

Furaltadone VETRANAL®, analytical standard

Supelco

46289

Furaltadone

AOZ VETRANAL®, analytical standard

Supelco

33347

AOZ

Am J Physiol Heart Circ Physiol. Furazolidone increases thapsigargin-sensitive Ca2+-ATPase in chick cardiac myocytes
D. Lax, R. Martinez-Zaguilan, et al.
American Journal of Physiology. Heart and Circulatory Physiology, 267, H734-H741 (1994)
B H Ali et al.
Quarterly journal of experimental physiology (Cambridge, England), 67(3), 437-448 (1982-07-01)
Furazolidone (0.4% w/w in the feed, 10 days) reduced the feed intake and growth in 9 week old chickens, and increased the amount of 5-hydroxytryptamine (5-HT) in the brain. The drug also increased the stimulation of transketolase activity by thiamine
B H Ali
Veterinary research communications, 6(1), 1-11 (1983-01-01)
The pharmacological and toxicological properties of furazolidone have been briefly reviewed. Among the most important pharmacological actions of furazolidone is the inhibition of mono- and diamine oxidase activities, which seem to depend, at least in some species, on the presence
Hafez Fakheri et al.
Helicobacter, 17(1), 43-48 (2012-01-10)
Sequential regimens have been recently reported to be superior to the standard triple therapies in Helicobacter pylori eradication, but most of these studies were performed in Europe and data from developing countries are lacking. So we designed a study to
André Gustavo Tempone et al.
International journal of antimicrobial agents, 36(2), 159-163 (2010-06-18)
Drug delivery systems are promising pharmaceutical formulations used to improve the therapeutic index of drugs. In this study, we developed a liposomal formulation of furazolidone that targets Leishmania (Leishmania) chagasi amastigotes in a hamster model. Using laser scanning confocal microscopy
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