3D Mol Similar

Furazolidone

: 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+

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1. Names and Identifiers

: 1.1 Name; Furazolidone; 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; View all

1.3 CAS No.: 67-45-8

1.4 CID: 5323714

1.5 EINECS(EC#): 200-653-3

1.6 Molecular Formula: C8H7N3O5 (isomer)

1.7 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/b9-5+

1.8 InChIkey: PLHJDBGFXBMTGZ-WEVVVXLNSA-N

1.9 Canonical Smiles: C1COC(=O)N1N=CC2=CC=C(O2)[N+](=O)[O-]

1.10 Isomers Smiles: C1COC(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-]

2. Properties

2.1 Density: 1.66

2.1 Melting point: 254-256°C (dec.)

2.1 Boiling point: 353.4 °C at 760 mmHg

2.1 Refractive index: 1.669

2.1 Flash Point: 353.4 °C at 760 mmHg

2.1 Precise Quality: 225.03900

2.1 PSA: 100.86000

2.1 logP: 1.43500

2.1 Solubility: formic acid: soluble50mg/mL

2.2 Λmax: 365nm(DMSO)(lit.)

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: Odorless

2.10 Physical: Solid

2.11 pKa: -1.98±0.20(Predicted)

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: 0-6°C

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; View all

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: Antimicrobial.

4. Safety and Handling

4.1 Symbol: GHS08;

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R62

4.1 Safety Statements: S36

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: H361

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.

4.4 RIDADR: 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: P281

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: 3

4.6 RTECS: RQ3675000

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 NO_x.
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*

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	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.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Mass spectrum (electron ionization)

7. Synthesis Route

67-45-8Total: 8 Synthesis Route

405-22-1 2 Suppliers

67-45-8 268 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 77, p. 2282
Yield: null

6270-33-3 2 Suppliers

67-45-8 268 Suppliers

Literatures:
US2898335 , ;
Yield: null

5407-76-1

67-45-8 268 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 77, p. 2282
Yield: null

View all

8. Precursor and Product

precursor:

405-22-1

28127-20-0

6270-33-3

92-55-7

698-63-5

109-84-2

80-65-9

5407-76-1

105-58-8

75-44-5

product :

83796-92-3

69094-15-1

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
CACTVS Substructure Key Fingerprint: AAADcYBzOAAAAAAAAAAAAAAAAAAAAWJAAAAAAAAAAAAAAAABgAAAHgAMAAAACAThkAYwjIIQRECpALFzWwSSCAAsIgA6iAEubNoOJrKEtZuLGSDkzhEY6Ya8AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What are the differences between Furazolidone and Furantoin? Feb 26 2023
Furazolidone and Furantoin are both nitrofuran antibacterial drugs and are considered to be relatively old antibiotics. The main differences between the two drugs are: Different spectrum of antibacter..
What is Furazolidone and what are its effects? Nov 15 2022
Furazolidone has a wide range of applications in various industries, including the aquaculture industry, where it has excellent antibacterial properties. But what exactly is Furazolidone and what are ..
What is the in vitro activity of furazolidone and its uses in treating various infections? Mar 08 2022
Furazolidone exhibits in vitro activity against a range of bacteria including S. aureus, S. pyogenes, Enterococcus faecalis, E. coli, Vibrio cholerae, Clostrida spp., Klebsiella, Enterobacter, Salmone..
What should we pay attention to when taking Furazolidone? Feb 23 2022
There are various types of antibiotic drugs, but it is essential to understand key information such as the illness and the duration of the disease before blindly choosing. Furazolidone is primarily us..