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F9505

Sigma-Aldrich

Furazolidon

Synonym(e):

3-(5-Nitrofurfurylidenamino)-2-oxazolidinon

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About This Item

Empirische Formel (Hill-System):
C8H7N3O5
CAS-Nummer:
67-45-8
Molekulargewicht:
225.16
Beilstein:
8317414
EG-Nummer:
200-653-3
MDL-Nummer:
MFCD00010550
UNSPSC-Code:
51102829
PubChem Substanz-ID:
24894997
NACRES:
NA.85

Biologische Quelle

synthetic

Qualitätsniveau

200

Form

powder

Farbe

yellow

mp (Schmelzpunkt)

256-256 °C

Löslichkeit

formic acid: 50 mg/mL

Wirkungsspektrum von Antibiotika

Gram-positive bacteria
parasites

Wirkungsweise

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+

InChIKey

PLHJDBGFXBMTGZ-WEVVVXLNSA-N

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Anwendung

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. Wirkung

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.

Piktogramme

Health hazard
GHS08

Signalwort

Warning

H-Sätze

H361fd

Gefahreneinstufungen

Repr. 2

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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Nitrofurazon United States Pharmacopeia (USP) Reference Standard

USP

1465004

Nitrofurazon

Flurbiprofen cyclooxygenase inhibitor

Sigma-Aldrich

F8514

Flurbiprofen

Nitrofural Unreinheit B European Pharmacopoeia (EP) Reference Standard

Y0001570

Nitrofural Unreinheit B

Furaltadon VETRANAL®, analytical standard

Supelco

46289

Furaltadon

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
A C de Groot et al.
Contact dermatitis, 22(4), 202-205 (1990-04-01)
A case of occupational contact allergy to furazolidone, used as an animal feed additive and as an antimicrobial drug in veterinary medicine, is described. The patient did not react to furazolidone 2% pet. Using PEG-400 and alcohol as patch test
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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