ContaminantDB: Nitrofural

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:14:52 UTC

Update Date

2016-11-09 01:09:12 UTC

Accession Number

CHEM003709

Identification

Common Name

Nitrofural

Class

Small Molecule

Description

A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial wounds, burns, ulcers, and skin infections. Nitrofurazone has also been administered orally in the treatment of trypanosomiasis.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 3
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Anti-Infective Agent
Drug
Household Toxin
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Nitro-2-furaldehyde semicarbazone	Kegg
Nitrofural	Kegg
Furacin	Kegg
NFZ	HMDB
Nitrofurazan	HMDB
Furacilin	HMDB
Furacillin	HMDB
Nitrofurazone, calcium (2:1) salt	HMDB

Chemical Formula

C₆H₆N₄O₄

Average Molecular Mass

198.136 g/mol

Monoisotopic Mass

198.039 g/mol

CAS Registry Number

59-87-0

IUPAC Name

[(E)-[(5-nitrofuran-2-yl)methylidene]amino]urea

Traditional Name

nitrofurazone

SMILES

NC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=O

InChI Identifier

InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+

InChI Key

IAIWVQXQOWNYOU-FPYGCLRLSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as nitrofurans. Nitrofurans are compounds containing a furan ring which bears a nitro group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furans

Sub Class

Nitrofurans

Direct Parent

Nitrofurans

Alternative Parents

Substituents

Nitroaromatic compound
2-nitrofuran
Semicarbazone
Semicarbazide
Heteroaromatic compound
C-nitro compound
Carbonic acid derivative
Organic nitro compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic zwitterion
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	238 dec°C
Boiling Point	Not Available
Solubility	210 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.27 g/L	ALOGPS
logP	0.23	ALOGPS
logP	-0.14	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.79	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	126.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.21 m³·mol⁻¹	ChemAxon
Polarizability	16.92 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-6900000000-ab197de8a008fa662f84	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-053r-8900000000-fb74d5d88d31817fc4fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-053r-9700000000-74ab81d6c8af01bd4c9f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-05o1-9100000000-3bfaf343549c655346fd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-05o1-9300000000-0e1b313ba36c19497a2f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-053r-9700000000-b6d6c2a8031086e8b668	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0002-9000000000-955108ce74e1ade052dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00nb-9100000000-b1c82af570ca70ff4e2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1900000000-1d212d3b29501750343d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0005-2900000000-92bf34b3a15306ef76e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-076u-9100000000-5e4b72f2b73083a73482	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-2900000000-9af17389b9526ffe0577	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9600000000-5ad22b05c4609624cd57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9000000000-e4513cbb2f82a212f579	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-96f86f6fac5c42a70472	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052g-9200000000-acad3af6af9f29b9a5e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-fbefaa72589c442a1324	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-724e2d600be54174b51d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5j-0900000000-c322c50510d759eea883	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9300000000-053c8b358b6df0eaa592	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0pb9-9500000000-c26d5be0126e0a0e8278	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Well absorbed.

Mechanism of Toxicity

The exact mechanism of action is unknown. Nitrofurazone inhibits several bacterial enzymes, especially those involved in the aerobic and anaerobic degradation of glucose and pyruvate. This activity is believed also to affect pyruvate dehydrogenase, citrate synthetase, malate dehydrogenase, glutathione reductase, and pyruvate decarboxylase.

Metabolism

Nitrofurans, including nitrofural, undergo metabolic reduction at the nitro group to generate reactive species which can covalently bind to cellular macromolecules. Half Life: 5 hours

Toxicity Values

Rat LD₅₀ = 590 mg/kg

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (1)

Uses/Sources

For the treatement of bacterial skin infections including pyodermas, infected dermatoses and infections of cuts, wounds, burns and ulcers due to susceptible organisms.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Allergic contact dermatitis is the most frequently reported adverse effect, occurring in approximately 1 % of patients treated.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID