U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H6N4O4
Molecular Weight 198.1365
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NITROFURAZONE

SMILES

c1cc(N(=O)=O)oc1/C(/[H])=N/NC(=N)O

InChI

InChIKey=IAIWVQXQOWNYOU-FPYGCLRLSA-N
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+

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including: https://en.wikipedia.org/wiki/Nitrofural | http://www.fao.org/fileadmin/user_upload/vetdrug/docs/41-5-nitrofurazone.pdf | http://www.druginfosys.com/drug.aspx?drugcode=942

Nitrofurazone is used to treat burns that have become infected. It is also used to treat skin infections due to skin grafts. It works by killing bacteria or preventing their growth. 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. The severe or irreversible adverse effects of Nitrofurazone, which give rise to further complications include Peripheral neuropathy, Thromboembolic disorder.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P38489
Gene ID: 945778.0
Gene Symbol: nfsB
Target Organism: Escherichia coli (strain K12)
12.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FURACIN

Approved Use

Nitrofurazone is used to treat burns that have become infected.

Launch Date

-7.6507198E11
Curative
FURACIN

Approved Use

It is used to treat skin infections due to skin grafts

Launch Date

-7.6507198E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.8 μg/mL
6.35 mg/kg single, intravenous
dose: 6.35 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NITROFURAZONE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.263 μg/mL
63.5 mg/kg single, oral
dose: 63.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
NITROFURAZONE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
73.47 μg × min/mL
6.35 mg/kg single, intravenous
dose: 6.35 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NITROFURAZONE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
844.79 μg × min/mL
63.5 mg/kg single, oral
dose: 63.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
NITROFURAZONE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
17.32 min
6.35 mg/kg single, intravenous
dose: 6.35 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
NITROFURAZONE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
276.09 min
63.5 mg/kg single, oral
dose: 63.5 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
NITROFURAZONE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
0.2 % 1 times / day multiple, topical
Dose: 0.2 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.2 %, 1 times / day
Sources:
unhealthy, 51 ±17 years (range: 14 - 85 years)
n = 58
Health Status: unhealthy
Age Group: 51 ±17 years (range: 14 - 85 years)
Sex: M+F
Population Size: 58
Sources:
Disc. AE: Allergic contact dermatitis...
AEs leading to
discontinuation/dose reduction:
Allergic contact dermatitis (severe, 59%)
Sources:
0.02 % 1 times / day multiple, ophthalmic
Dose: 0.02 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.02 %, 1 times / day
Co-administed with::
chloramphenicol
neomycin-bacitracin-polimixin B
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Condition: conjuctivitis
Age Group: 70 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Erythema, Oedema...
AEs leading to
discontinuation/dose reduction:
Erythema (1 patient)
Oedema (1 patient)
Pruritus (1 patient)
Sources:
0.2 % 2 times / day multiple, otic
Dose: 0.2 %, 2 times / day
Route: otic
Route: multiple
Dose: 0.2 %, 2 times / day
Co-administed with::
hydrocortisone acetate(0.01)
Sources:
unhealthy
n = 46
Health Status: unhealthy
Condition: ears infection
Population Size: 46
Sources:
Disc. AE: Allergy...
AEs leading to
discontinuation/dose reduction:
Allergy (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Allergic contact dermatitis severe, 59%
Disc. AE
0.2 % 1 times / day multiple, topical
Dose: 0.2 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.2 %, 1 times / day
Sources:
unhealthy, 51 ±17 years (range: 14 - 85 years)
n = 58
Health Status: unhealthy
Age Group: 51 ±17 years (range: 14 - 85 years)
Sex: M+F
Population Size: 58
Sources:
Erythema 1 patient
Disc. AE
0.02 % 1 times / day multiple, ophthalmic
Dose: 0.02 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.02 %, 1 times / day
Co-administed with::
chloramphenicol
neomycin-bacitracin-polimixin B
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Condition: conjuctivitis
Age Group: 70 years
Sex: M
Population Size: 1
Sources:
Oedema 1 patient
Disc. AE
0.02 % 1 times / day multiple, ophthalmic
Dose: 0.02 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.02 %, 1 times / day
Co-administed with::
chloramphenicol
neomycin-bacitracin-polimixin B
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Condition: conjuctivitis
Age Group: 70 years
Sex: M
Population Size: 1
Sources:
Pruritus 1 patient
Disc. AE
0.02 % 1 times / day multiple, ophthalmic
Dose: 0.02 %, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 0.02 %, 1 times / day
Co-administed with::
chloramphenicol
neomycin-bacitracin-polimixin B
Sources:
unhealthy, 70 years
n = 1
Health Status: unhealthy
Condition: conjuctivitis
Age Group: 70 years
Sex: M
Population Size: 1
Sources:
Allergy 2 patients
Disc. AE
0.2 % 2 times / day multiple, otic
Dose: 0.2 %, 2 times / day
Route: otic
Route: multiple
Dose: 0.2 %, 2 times / day
Co-administed with::
hydrocortisone acetate(0.01)
Sources:
unhealthy
n = 46
Health Status: unhealthy
Condition: ears infection
Population Size: 46
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

PubMed

PubMed

TitleDatePubMed
Antibacterial nitrofuran derivatives. I. 5-nitro-2-furaldehyde semicarbazones and thiosemicarbazones.
1967 Jul
[Nitrofural (Furacin) polyneuropathy].
1971 Aug
Structure/activity relationships for the enhancement by electron-affinic drugs of the anti-tumour effect of CCNU.
1982 Aug
Inhibition of rabbit liver monoamine oxidase by nitro aromatic compounds.
1982 Aug 15
Activation of misonidazole by rat liver microsomes and purified NADPH-cytochrome c reductase.
1982 Feb 15
Effects of furazolidone or nitrofurazone on the concentrations of hypothalamic amines and plasma luteinizing hormone (LH) and prolactin (PRL), levels in young turkeys.
1988
[Acute kidney failure due to a nitrofurazone cream].
1993 Apr
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.
1996 Dec
Bactericidal activity of nitrofurans against growing and dormant Mycobacterium bovis BCG.
2000 Dec
A mechanistic study of ovarian carcinogenesis induced by nitrofurazone using rasH2 mice.
2000 Sep-Oct
CoMFA-SIMCA model for antichagasic nitrofurazone derivatives.
2001 Apr
Development of polyvinyl alcohol-sodium alginate gel-matrix-based wound dressing system containing nitrofurazone.
2008 Jul 9
Wound healing activity and docking of glycogen-synthase-kinase-3-beta-protein with isolated triterpenoid lupeol in rats.
2008 Sep
Nitroreductive metabolic activation of some carcinogenic nitro heterocyclic food contaminants in rat mammary tissue cellular fractions.
2009 Jan
Patents

Sample Use Guides

Apply directly on the lesion with a spatula or first place on a piece of gauze. Use of a bandage is optional. The preparation should remain on the lesion for at least 24 hours. The dressing may be changed several times daily or left on the lesion for a longer period.
Route of Administration: Topical
Nitrofurazone significantly enhanced proliferation of MCF-7 cells at 100 nM (P<0.05) and 1–10 mM (P<0.001).
Name Type Language
NITROFURAZONE
GREEN BOOK   HSDB   INCI   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF  
INCI  
Official Name English
FURACIN
Brand Name English
NSC-2100
Code English
NITROFURAZONE [ORANGE BOOK]
Common Name English
NITROFURAZONE [VANDF]
Common Name English
NITROFURAZONE [MART.]
Common Name English
NITROFURAL [WHO-DD]
Common Name English
NITROFURAZONE [USP-RS]
Common Name English
NITROFURAZONE [HSDB]
Common Name English
NITROFURAZONE [USP]
Common Name English
5-NITRO-2-FURALDEHYDE SEMICARBAZONE
Systematic Name English
HYDRAZINECARBOXAMIDE, 2-((5-NITRO-2-FURANYL)METHYLENE)
Systematic Name English
NITROFURAL [IARC]
Common Name English
NITROFURAL
EP   INN   WHO-DD  
INN  
Official Name English
ACTIN-N
Brand Name English
NITROFURAL [INN]
Common Name English
NITROFURAZONE [INCI]
Common Name English
NITROFURAL [EP MONOGRAPH]
Common Name English
NITROFURAZONE [GREEN BOOK]
Common Name English
NSC-1602
Code English
NITROFURAZONE [MI]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 524.1580
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-VATC QS01AX04
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-ATC D08AF01
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-VATC QB05CA03
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-ATC S02AA02
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
CFR 21 CFR 530.41
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-VATC QG01AX90
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-ATC P01CC02
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
NCI_THESAURUS C29698
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-VATC QS02AA02
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-VATC QD08AF01
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
IARC Nitrofural (Nitrofurazone)
WHO-ATC D09AA03
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-ATC B05CA03
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-VATC QD09AA03
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-VATC QP51AC02
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
CFR 21 CFR 524.1580A
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
WHO-ATC S01AX04
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
CFR 21 CFR 524.1580B
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
CFR 21 CFR 524.1580C
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
Code System Code Type Description
INN
4160
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
NCI_THESAURUS
C73150
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
EPA CompTox
59-87-0
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
FDA UNII
X8XI70B5Z6
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
DRUG CENTRAL
1950
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
MESH
D009583
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-443-1
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
RXCUI
7455
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY RxNorm
EVMPD
SUB09325MIG
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
CAS
59-87-0
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
USP_CATALOG
1465004
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY USP-RS
PUBCHEM
5447130
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
DRUG BANK
DB00336
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL869
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
HSDB
3136
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY
MERCK INDEX
M7957
Created by admin on Fri Jun 25 21:18:57 UTC 2021 , Edited by admin on Fri Jun 25 21:18:57 UTC 2021
PRIMARY Merck Index