NITROFURAZONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H6N4O4
Molecular Weight	198.1362
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)N\N=C\C1=CC=C(O1)[N+]([O-])=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
Sources: https://www.drugs.com/cons/nitrofurazone-topical.html
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxygen-insensitive NAD(P)H nitroreductase 1 Target ID: P38489 Gene ID: 945778.0 Gene Symbol: nfsB Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15684426	Substrate 661		12.0 µM [Ki]
DNA 282 Target ID: CHEMBL2364041 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12069963 \| https://www.ncbi.nlm.nih.gov/pubmed/22355582 \| https://www.ncbi.nlm.nih.gov/pubmed/15488632	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infected burns 1 Sources: https://www.drugs.com/cons/furacin-topical.html	Primary		Approved 8583	FURACIN Approved Use Nitrofurazone is used to treat burns that have become infected. Launch Date 1945
Skin infections due to skin grafts 1 Sources: https://www.drugs.com/cons/furacin-topical.html https://www.ncbi.nlm.nih.gov/pubmed/3516908	Curative		Approved 8583	FURACIN Approved Use It is used to treat skin infections due to skin grafts Launch Date 1945

C_max

Value	Dose	Co-administered	Analyte	Population
2.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23957951/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23957951/	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

Value	Dose	Co-administered	Analyte	Population
73.47 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23957951/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23957951/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
17.32 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23957951/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23957951/	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/31616212	unhealthy, 51 ±17 years (range: 14 - 85 years) Health Status: unhealthy Age Group: 51 ±17 years (range: 14 - 85 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31616212	Disc. AE: Allergic contact dermatitis... AEs leading to discontinuation/dose reduction: Allergic contact dermatitis (severe, 59%) Sources: https://pubmed.ncbi.nlm.nih.gov/31616212
0.02 % 1 times / day multiple, ophthalmic Dose: 0.02 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.02 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2931241	unhealthy, 70 years Health Status: unhealthy Age Group: 70 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/2931241	Disc. AE: Erythema, Oedema... AEs leading to discontinuation/dose reduction: Erythema (1 patient) Oedema (1 patient) Pruritus (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2931241
0.2 % 2 times / day multiple, otic Dose: 0.2 %, 2 times / day Route: otic Route: multiple Dose: 0.2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5436960	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/5436960	Disc. AE: Allergy... AEs leading to discontinuation/dose reduction: Allergy (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/5436960

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/31616212	unhealthy, 51 ±17 years (range: 14 - 85 years) Health Status: unhealthy Age Group: 51 ±17 years (range: 14 - 85 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/31616212
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 Sources: https://pubmed.ncbi.nlm.nih.gov/2931241	unhealthy, 70 years Health Status: unhealthy Age Group: 70 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/2931241
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 Sources: https://pubmed.ncbi.nlm.nih.gov/2931241	unhealthy, 70 years Health Status: unhealthy Age Group: 70 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/2931241
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 Sources: https://pubmed.ncbi.nlm.nih.gov/2931241	unhealthy, 70 years Health Status: unhealthy Age Group: 70 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/2931241
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 Sources: https://pubmed.ncbi.nlm.nih.gov/5436960	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/5436960

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 150 inhibitor 2252

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 OATP1B3 961

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMODY5In19	inconclusive [Activation 31.6228 uM]
CYP3A4 2633	activator 342 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMODY5In19	no [Activation >31.6228 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDg2OSJ9fQ%3D%3D	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDg2OSJ9fQ%3D%3D	yes [Inhibition 10 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:44368	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:44368
ZINC	ZINC000253624240	http://zinc15.docking.org/substances/ZINC000253624240

PubMed

Title	Date	PubMed
Nitroreductive metabolic activation of some carcinogenic nitro heterocyclic food contaminants in rat mammary tissue cellular fractions.	2009-01	19017535
Wound healing activity and docking of glycogen-synthase-kinase-3-beta-protein with isolated triterpenoid lupeol in rats.	2008-09	18222664
Development of polyvinyl alcohol-sodium alginate gel-matrix-based wound dressing system containing nitrofurazone.	2008-07-09	18440737
Nitrofurazone-induced gene expressions in rat hepatocytes and their modification by N-acetylcysteine.	2005-04	15945272
Mechanism of carcinogenesis induced by a veterinary antimicrobial drug, nitrofurazone, via oxidative DNA damage and cell proliferation.	2004-11-25	15488632
Testicular toxicity of nitrofurazone causing germ cell apoptosis in rats.	2001-07	11548123
CoMFA-SIMCA model for antichagasic nitrofurazone derivatives.	2001-04	11354658
Bactericidal activity of nitrofurans against growing and dormant Mycobacterium bovis BCG.	2000-12	11102410
A mechanistic study of ovarian carcinogenesis induced by nitrofurazone using rasH2 mice.	2000-10-12	11026599
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996-12	9039272
[Acute kidney failure due to a nitrofurazone cream].	1993-04	8497731
Effects of furazolidone or nitrofurazone on the concentrations of hypothalamic amines and plasma luteinizing hormone (LH) and prolactin (PRL), levels in young turkeys.	1988	3126094
Inhibition of rabbit liver monoamine oxidase by nitro aromatic compounds.	1982-08-15	6814441
Structure/activity relationships for the enhancement by electron-affinic drugs of the anti-tumour effect of CCNU.	1982-08	7150475
Activation of misonidazole by rat liver microsomes and purified NADPH-cytochrome c reductase.	1982-02-15	6802140
[Nitrofural (Furacin) polyneuropathy].	1971-08	4998032
Antibacterial nitrofuran derivatives. I. 5-nitro-2-furaldehyde semicarbazones and thiosemicarbazones.	1967-07	4962510

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

Official Name

English

NITROFURAL

Preferred Name

English

NITROFURAZONE [USP MONOGRAPH]

Common 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

NITROFURAZONE [USP-RS]

Common Name

English

NITROFURAZONE [HSDB]

Common Name

English

Nitrofural [WHO-DD]

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

ACTIN-N

Brand Name

English

nitrofural [INN]

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