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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=C1C(=O)N\N=C\C2=CC=C(O2)[N+]([O-])=O)[N+]([O-])=O)[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
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
Histomonastatic activity of nifursol in turkeys.
1969 Mar
Gas-liquid chromatographic determination of nifursol in frozen turkey tissues to ten parts per billion.
1975 Jul
High pressure liquid chromatographic determination of nifursol in finished feeds.
1981 Jul

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.
Name Type Language
NIFURSOL
INN   MART.   USAN  
USAN   INN  
Official 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
NSC-759632
Code English
NIFURSOL [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QP51AX05
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Code System Code Type Description
CAS
16915-70-1
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PRIMARY
NCI_THESAURUS
C170223
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ChEMBL
CHEMBL485549
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INN
2511
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FDA UNII
TG99GOU55Z
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MESH
C032119
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EVMPD
SUB09278MIG
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EPA CompTox
DTXSID0046226
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ECHA (EC/EINECS)
240-963-6
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PUBCHEM
9570327
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NSC
759632
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SMS_ID
100000083877
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