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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/REAXYS Number:
8317414
EC Number:
200-653-3
MDL number:
MFCD00010550
UNSPSC Code:
51101500
PubChem Substance ID:
24894997
NACRES:
NA.85

biological source

synthetic

Quality Level

200

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

signalword

Warning

hcodes

H361fd

Hazard Classifications

Repr. 2

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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

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

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
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)
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
Xi Jin et al.
Toxicology letters, 201(3), 205-212 (2011-01-05)
Furazolidone (FZD) is an antimicrobial agent that has been shown to have mutagenic, genotoxic and potentially carcinogenic properties when tested in a variety of systems in vitro and in vivo. In this study, we investigated FZD's DNA damaging effect in
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
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