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

Details

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

SHOW SMILES / InChI
Structure of NITROFURAZONE

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

Molecular Formula C6H6N4O4
Molecular Weight 198.1362
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
12.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FURACIN
Curative
FURACIN

Cmax

ValueDoseCo-administeredAnalytePopulation
2.8 μg/mL
6.35 mg/kg single, intravenous
NITROFURAZONE plasma
Oryctolagus cuniculus
0.263 μg/mL
63.5 mg/kg single, oral
NITROFURAZONE plasma
Oryctolagus cuniculus

AUC

ValueDoseCo-administeredAnalytePopulation
73.47 μg × min/mL
6.35 mg/kg single, intravenous
NITROFURAZONE plasma
Oryctolagus cuniculus
844.79 μg × min/mL
63.5 mg/kg single, oral
NITROFURAZONE plasma
Oryctolagus cuniculus

T1/2

ValueDoseCo-administeredAnalytePopulation
17.32 min
6.35 mg/kg single, intravenous
NITROFURAZONE plasma
Oryctolagus cuniculus
276.09 min
63.5 mg/kg single, oral
NITROFURAZONE plasma
Oryctolagus cuniculus

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

PubMed

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).
Substance Class Chemical
Record UNII
X8XI70B5Z6
Record Status Validated (UNII)
Record Version