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Compound Detail

CHEMBL869

NITROFURAZONE
💊 Approved Drug
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💊 Approved Drug
NC(=O)N/N=C/c1ccc([N+](=O)[O-])o1

Basic Information

ChEMBL ID CHEMBL869
Name NITROFURAZONE
Phase Approved
Structure Type MOL
InChI Key IAIWVQXQOWNYOU-FPYGCLRLSA-N
Therapeutic ✓ Yes

Known Names

Actin-n Furacin Furacine Nitrofural Nitrofurazone NSC-1602 NSC-2100
6
Targets
20
Activities
3
Assay Types
0
PK Parameters
20
Publications
7
Known Names
5
Indications
1
Mechanisms

Molecular Properties

198.1
MW (Da)
0.19
ALogP
5
HBA
2
HBD
123.8
PSA (Ų)
0.41
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1945
Availability Withdrawn
Chirality Achiral

Routes of Administration

Topical

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C6H6N4O4
MW 198.14
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -2.33

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA

Indications

Eye Infections Leishmaniasis Trypanosomiasis Amyotrophic Lateral Sclerosis Osteomyelitis

ATC Classification

B05CA03
nitrofural
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: BLOOD SUBSTITUTES AND PERFUSION SOLUTIONS
D08AF01
nitrofural
Level 1: DERMATOLOGICALS
Level 2: ANTISEPTICS AND DISINFECTANTS
D09AA03
nitrofural
Level 1: DERMATOLOGICALS
Level 2: MEDICATED DRESSINGS
P01CC02
nitrofural
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTIPROTOZOALS
S01AX04
nitrofural
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02AA02
nitrofural
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS

Drug Warnings

Withdrawn
General Warning
superseded by safer and more effective preparations
Country: United States; Japan   Year: 1977
Withdrawn
carcinogenicity
mammary tumors in rats and ovarian tumors in mice
Country: United States; Japan   Year: 1977

Activity Summary

IC50 15 meas. best 5.77
EC50 4 meas. best 6.51
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma brucei
CHEMBL612849
EC50 6.51 5.79 310.0 3
Leishmania donovani
CHEMBL367
IC50 5.77 5.638 1690.0 5
Leishmania major
CHEMBL612879
IC50 5.73 5.565 1850.0 4
Trypanosoma cruzi
CHEMBL368
IC50 5.65 5.38 2230.0 2
Trypanosoma cruzi
CHEMBL368
EC50 5.1 5.1 8000.0 1
Snake venom metalloproteinase BaP1
CHEMBL2079851
IC50 4.05 4.05 88100.0 1
NAD(+) hydrolase SARM1
CHEMBL4523350
IC50 4.05 4.05 90000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma brucei EC50 = 310.0 nM 6.51 Antimicrobial activity against Trypanosoma brucei 20439607
Leishmania donovani IC50 = 1690.0 nM 5.77 Antileishmanial activity against Leishmania donovani MHOM/IN/95/9515 amastigote ... 37859713
Leishmania major IC50 = 1850.0 nM 5.73 Antileishmanial activity against Leishmania major IR-173 promastigotes assessed ... 37859713
Leishmania donovani IC50 = 1850.0 nM 5.73 Antileishmanial activity against Leishmania donovani MHOM/IN/95/9515 promastigot... 37859713
Leishmania major IC50 = 1850.0 nM 5.73 Antileishmanial activity against Leishmania major IR-173 promastigotes assessed ... 36516584
Leishmania donovani IC50 = 1850.0 nM 5.73 Antileishmanial activity against Leishmania donovani 9515 promastigotes assessed... 36516584
Trypanosoma cruzi IC50 = 2230.0 nM 5.65 Antitrypanosomal activity against bloodstream Trypanosoma cruzi trypomastigotes ... 37859713
Leishmania donovani IC50 = 2700.0 nM 5.57 Leishmanicidal activity against Leishmania donovani 9515 amastigote infected in ... 36516584
Leishmania major IC50 = 2800.0 nM 5.55 Antileishmanial activity against Leishmania major IR-173 amastigote infected in ... 36516584
Trypanosoma brucei EC50 = 3700.0 nM 5.43 Antimicrobial activity against Trypanosoma brucei NfxR1 20439607
Trypanosoma brucei EC50 = 3700.0 nM 5.43 Antimicrobial activity against Trypanosoma brucei NfxR2 20439607
Leishmania donovani IC50 = 4110.0 nM 5.39 Antileishmanial activity against Leishmania donovani 9515 amastigote infected in... 36516584
Leishmania major IC50 = 5600.0 nM 5.25 Leishmanicidal activity against Leishmania major IR-173 amastigote infected in h... 36516584
Trypanosoma cruzi IC50 = 7830.0 nM 5.11 Antitrypanosomal activity against Trypanosoma cruzi epimastigotes assessed as pa... 37859713
Trypanosoma cruzi EC50 = 8000.0 nM 5.1 Antitrypanosomal activity against Trypanosoma cruzi amastigotes infected in BESM... 20547819
Snake venom metalloproteinase BaP1 IC50 = 88100.0 nM 4.05 Inhibition of snake venom BaP1 using Abz-Ala-Gly-Leu-Ala-Nba as substrate incuba... 24900507
NAD(+) hydrolase SARM1 IC50 = 90000.0 nM 4.05 Inhibition of recombinant human SARM1 TIR domain (561 to 724 residues) expressed... 32828421

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1415
22546205 10.1016/j.bmc.2012.04.004 ADMET 11
19223619 10.1128/aac.01449-08 Helicobacter pylori 8
20566772 10.1128/aac.01451-09 Trypanosoma cruzi 7
37859713 10.1039/d3md00220a ADMET 6
18722035 10.1016/j.ejmech.2008.07.006 Rattus norvegicus 6
- 10.1007/s00044-011-9860-5 Rattus norvegicus 6
20439607 10.1128/aac.00332-10 Trypanosoma brucei 5
36516584 10.1016/j.ejmech.2022.115012 ADMET 5
12540242 10.1021/jm021030a Trypanosoma brucei 5
36516584 10.1016/j.ejmech.2022.115012 Unchecked 4
12540242 10.1021/jm021030a Mus musculus 4
812994 10.1021/jm00223a013 Escherichia coli 4
20566772 10.1128/aac.01451-09 Mus musculus 4
36516584 10.1016/j.ejmech.2022.115012 Leishmania donovani 3
32828421 10.1016/j.bmc.2020.115644 NAD(+) hydrolase SARM1 3
36516584 10.1016/j.ejmech.2022.115012 Leishmania major 3
20014752 10.1021/tx900326k Hepatotoxicity 3
18295489 10.1016/j.bmc.2007.11.029 Rattus norvegicus 2
12540242 10.1021/jm021030a Leishmania infantum 2

Data from ChEMBL 36 via Core Engine