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

Details

Stereochemistry ACHIRAL
Molecular Formula C12H7N5O9
Molecular Weight 365.2121
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NIFURSOL

SMILES

OC1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)C(=O)N\N=C\C2=CC=C(O2)[N+]([O-])=O

InChI

InChIKey=XXUXXCZCUGIGPP-WLRTZDKTSA-N
InChI=1S/C12H7N5O9/c18-11-8(3-6(15(20)21)4-9(11)16(22)23)12(19)14-13-5-7-1-2-10(26-7)17(24)25/h1-5,18H,(H,14,19)/b13-5+

HIDE SMILES / InChI

Molecular Formula C12H7N5O9
Molecular Weight 365.2121
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Nifursol is an antibiotic of the nitrofuran class which inhibits the growth of the protozoa Histomonas meleagridis but is non-lethal. Although previously approved as a prophylactic feed additive for turkeys, the European Union has since banned Nifursol use in agricultural operations.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Analysis of nifursol residues in turkey and chicken meat using liquid chromatography-tandem mass spectrometry.
2005-02
Determination of nifursol in medicated animal feeds using high-performance liquid chromatography. Analytical Methods Committee.
1985-08
High pressure liquid chromatographic determination of nifursol in finished feeds.
1981-07
Gas-liquid chromatographic determination of nifursol in frozen turkey tissues to ten parts per billion.
1975-07
Histomonastatic activity of nifursol in turkeys.
1969-03

Sample Use Guides

In turkeys has been used as a feed additive at a level of 50 - 75 mg/kg (ppm) subject of a 5 day withdrawal period prior to slaughter.
Route of Administration: Oral
Histomonas meleagridis cultures were isolated from the droppings of chickens orally infected by Heterakis gallinarum, which subsequently developed Histomoniasis. Parasites and accompanying bacterial flora were cultured anaerobically at 39 deg-C on Stepkowski media. The accompanying flora, which are essential to in vitro culture of the parasite, were isolated from the cecum of infected birds. Nifursol was dissolved in dimethyl sulfoxide at 8 mg/mL. H. meleagridis cultures (10^6 parasites /mL) were incubated anaerobically for 24-hours at 39 deg-C. Nifursol was assayed in a range of concentrations between 12.5 - 400 micro-g/mL. The viability of cultures was determined at 6, 12, 24, and 48 hours. The minimum lethal concentration (MLC) was defined as the lowest drug concentration in which no live organisms were observed. Nifursol was effective against H. meleagridis even though it did not kill all parasites after 24, 48 and 72 hours. However, there was no time effect, regardless of concentration; therefore, Nifursol may be regarded as a growth inhibitor.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:34:18 GMT 2025
Edited
by admin
on Wed Apr 02 09:34:18 GMT 2025
Record UNII
TG99GOU55Z
Record Status Validated (UNII)
Record Version
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Name Type Language
NIFURSOL
INN   MART.   USAN  
USAN   INN  
Official Name English
NSC-759632
Preferred Name English
nifursol [INN]
Common Name English
NIFURSOL [USAN]
Common Name English
3,5-Dinitrosalicylic acid (5-nitrofurfurylidene)hydrazide
Common Name English
BENZOIC ACID, 2-HYDROXY-3,5-DINITRO-, ((5-NITRO-2-FURANYL)METHYLENE)HYDRAZIDE
Common Name English
NIFURSOL [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QP51AX05
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
Code System Code Type Description
CAS
16915-70-1
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
NCI_THESAURUS
C170223
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
ChEMBL
CHEMBL485549
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
INN
2511
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
FDA UNII
TG99GOU55Z
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
MESH
C032119
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
EVMPD
SUB09278MIG
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID0046226
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
ECHA (EC/EINECS)
240-963-6
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
PUBCHEM
9570327
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
NSC
759632
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
SMS_ID
100000083877
Created by admin on Wed Apr 02 09:34:18 GMT 2025 , Edited by admin on Wed Apr 02 09:34:18 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY