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Home> Encyclopedia >Antibiotic and antimicrobial agents>Pharmaceutical Intermediates>Pharmaceutical
Furazolidone structure
Furazolidone structure


Iupac Name:3-[(E)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
CAS No.: 67-45-8
Molecular Weight:225.16
Modify Date.: 2022-11-12 07:17
Introduction: Furazolidone belongs to the group of nitro furans. Thisantimicrobal (antibacterial and antiprotozoal) agent isused in veterinary medicine both topically and orally,particularly in animal feed. Reactions have beenreported in workers exposed to it by contact withanimal feed. Cross reactions with other nitrofuranderivatives are rare. View more+
1. Names and Identifiers
1.1 Name
1.2 Synonyms

2-Furanmethanimine, 5-nitro-N-(2-oxo-3-oxazolidinyl)- 2-Oxazolidinone, 3-((5-nitrofurfurylidene)amino)- 2-Oxazolidinone, 3-((5-nitrofurfurylidine)amino)- 2-Oxazolidinone, 3-[[(1E)-(5-nitro-2-furanyl)methylene]amino]- 2-Oxazolidinone, 3-[[(5-nitro-2-furanyl)methylene]amino]- 2-Oxazolidinone,3-[[(5-nitro-2-furanyl)methylene]amino]- 3-(((5-nitro-2-furanyl)methylene)amino)-2-oxazolidinon 3-(((5-Nitro-2-furanyl)methylene)amino)-2-oxazolidinone 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidinone 3-[(5-Nitrofurfurylidene)amino]-2-oxazolidone 3-[[(5-Nitro-2-furanyl)methylene]amino]-2-oxazolidinone 3-{(E)-[(5-Nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one 3-{[(E)-(5-Nitro-2-furyl)methylene]amino}-1,3-oxazolidin-2-one Bifuron EINECS 200-653-3 Furall Furaxon Furazol Furazon Furidon Furox MFCD00010550 Neftin nf-180

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1.3 CAS No.
1.4 CID
1.6 Molecular Formula
C8H7N3O5 (isomer)
1.7 Inchi
1.8 InChIkey
1.9 Canonical Smiles
1.10 Isomers Smiles
2. Properties
2.1 Density
2.1 Melting point
254-256°C (dec.)
2.1 Boiling point
353.4 °C at 760 mmHg
2.1 Refractive index
2.1 Flash Point
353.4 °C at 760 mmHg
2.1 Precise Quality
2.1 PSA
2.1 logP
2.1 Solubility
formic acid: soluble50mg/mL
2.2 Λmax
2.3 AnalyticLaboratory Methods
Thin-layer chromatography, high-pressure liquid chromatography, UV adsorption spectrophotometry or a combination of these techniques.
2.4 Appearance
yellow powder or crystalline powder
2.5 Storage
Light Sensitive. Ambient temperatures.
2.6 Color/Form
Yellow powder
2.7 Contact Allergens
Furazolidone belongs to the group of nitrofurans. This antimicrobial (antibacterial and antiprotozoal) agent is used in veterinary medicine both topically and orally, particularly in animal feed. Reactions are reported in workers exposed to it in animal feeds. Cross-reactions with other nitrofuran derivatives are rare.
2.8 Decomposition
When heated to decomposition it emits toxic fumes of /nitrogen oxides/.
2.9 Odor
2.10 Physical
2.11 pKa
2.12 Water Solubility
formic acid: soluble50mg/mL
2.13 Spectral Properties
IR: 5187 (Coblentz Society spectral collection)
UV: 6985 (Sadtler Research Laboratories spectral collection)
2.14 Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
2.15 StorageTemp
3. Use and Manufacturing
3.1 Definition
ChEBI: A member of the class of oxazolidines that is 1,3-oxazolidin-2-one in which the hydrogen attached to the nitrogen is replaced by an N-{[(5-nitro-2-furyl)methylene]amino} group. It has antibacterial and antiprotozoal properties, and is usd in the treatment of giardiasis and cholera.
3.2 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 34 companies from 7 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria by 2 of 34 companies. For more detailed information, please visit ECHA C&L website

Of the 6 notification(s) provided by 32 of 34 companies with hazard statement code(s):

H361 (87.5%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P281, P308+P313, P405, and P501
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3.3 Methods of Manufacturing
Prepn: GB 735136; G. Gever, US 2742462; G.D. Drake et al., US 2759931; G. Gever, C.J. O'Keefe, US 2927110 (1955, 1956, 1956, 1960 all to Norwich); G. Gever et al., J. Am. Chem. Soc. 77, 2277 (1955).
3.4 Usage
4. Safety and Handling
4.1 Symbol
4.1 Hazard Codes
4.1 Signal Word
4.1 Risk Statements
4.1 Safety Statements
4.1 Exposure Standards and Regulations
Furazolidone aerosol powder. (a) The product contains either 4 or 10 percent furazolidone in inert dispersing agent and propellant. ... (c) Indications of use: (i) Dogs. For treatment or prevention of bacterial infection of superficial wounds, abrasions, lacerations, and pyogenic dermatitis. (ii) Horses. For treatment or prevention of bacterial infection of superficial wounds, abrasions, lacerations, and following firing (heat or electrocautery) ... (iv) Horses and ponies. For treatment or prevention of bacterial infection of superficial wounds, abrasions, lacerations, caused by Staphylococcus aureus, Streptococcus ssp. and Proteus spp. sensitive to furazolidone.
Furazolidone. A tolerance of zero is established for residues of furazolidone in the uncooked edible tissues of swine.
4.2 Octanol/Water Partition Coefficient
log Kow= -0.04 [Debnath AK et al; J Med Chem 34: 786-797 (1991)] PubMed Abstract
4.3 Hazard Declaration
4.3 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
NONH for all modes of transport
4.4 Safety Profile
Poison by ingestion andintraperitoneal routes. Human systemiceffects by ingestion: dyspnea, respiratorydepression, and eosinophilta. Experimentalreproductive effects. Human mutation datareported. Questionable carcinogen. Whenheated to decomposition it emits toxicfumes of NOx.
4.5 Caution Statement
4.5 Formulations/Preparations
Furoxone tablets, 100 mg; liquid composition: each 15 ml tablespoonful contains Furoxone 50 mg per 15 ml (3.33 mg per ml) in a lightyellow aqueous vehicle
4.6 WGK Germany
4.6 Report

IARC Cancer Review: Group 3 IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT ?? IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 31 ,1983,p. 141.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.:?) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

4.7 Safety

Poison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: dyspnea, respiratory depression, and eosinophilia. Experimental reproductive effects. Human mutation data reported. Questionable carcinogen. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:?Xn
Risk Statements: 62-40
R62:Risk of impaired fertility.?
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 36-22
S36:Wear suitable protective clothing.?
S22:Do not breathe dust.
WGK Germany: 3

4.8 Specification

? 3-(5'-Nitrofurfuralamino)-2-oxazolidone , with CAS number of 67-45-8, can be called N-(5-Nitro-2-furfurylidene)-3-amino-2-oxazolidone ; N-(5-Nitro-2-furfurylidene)-3-aminooxazolidine-2-one ; Nicolen ; Nifurazolidonum ; Optazol ; Furox Aerosol Powder (Veterinary) ; 5-Nitro-N-(2-oxo-3-oxazolidinyl)-2-furanmethanimine ; 3-(((5-Nitro-2-furanyl)methylene)amino)-2-oxazolidinone ; 2-Oxazolidinone, 3-(((5-nitro-2-furanyl)methylene)amino)- ; 2-Oxazolidinone, 3-((5-nitrofurfurylidine)amino)- ; 2-Furanmethanimine, 5-nitro-N-(2-oxo-3-oxazolidinyl)- .?3-(5'-Nitrofurfuralamino)-2-oxazolidone (CAS NO.67-45-8) is a fungicide with wide antimicrobial spectrum, be used as anti-infection drugs, used in the treatment of bacterial dysentery, enteritis, also used for treatment of vaginal infection, in recent years, also used for Typhoid, and the effect is good.

4.9 Toxicity
1. ???

pic-esc 2?mg/L

??? MUREAV ?? Mutation Research. 156 (1985),69.
2. ???

cyt-hmn:lym 2?mg/L/72H

??? MUREAV ?? Mutation Research. 59 (1979),139.
3. ???

orl-man TDLo:11?mg/kg:PUL,BLD

??? ARDSBL ?? American Review of Respiratory Disease. 105 (1972),823.
4. ???

orl-rat LD50:2336?mg/kg

??? TXAPA9 ?? Toxicology and Applied Pharmacology. 18 (1971),185.
5. ???

orl-mus LD50:1782?mg/kg

??? TRSTAZ ?? Transactions of the Royal Society of Tropical Medicine and Hygiene. 74 (1980),43.
6. ???

ipr-mus LD50:300?mg/kg

??? PMDCAY ?? Progress in Medical Chemistry. 5 (1967),320.
7. ???

orl-ckn LDLo:150?mg/kg CLDND*

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2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Signal word


Hazard statement(s)

H361 Suspected of damaging fertility or the unborn child

Precautionary statement(s)

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.


P308+P313 IF exposed or concerned: Get medical advice/ attention.


P405 Store locked up.


P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification


9. Other Information
9.0 Usage
Monoamine oxidase inhibitor
10. Computational chemical data
  • Molecular Weight: 225.16g/mol
  • Molecular Formula: C8H7N3O5
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 225.03857033
  • Monoisotopic Mass: 225.03857033
  • Complexity: 326
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Topological Polar Surface Area: 101
  • Heavy Atom Count: 16
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
11. Question & Answer
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