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Details

Stereochemistry ACHIRAL
Molecular Formula C13H10N4O5
Molecular Weight 302.2423
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4,4'-DINITROCARBANILIDE

SMILES

[O-][N+](=O)C1=CC=C(NC(=O)NC2=CC=C(C=C2)[N+]([O-])=O)C=C1

InChI

InChIKey=JEZZOKXIXNSKQD-UHFFFAOYSA-N
InChI=1S/C13H10N4O5/c18-13(14-9-1-5-11(6-2-9)16(19)20)15-10-3-7-12(8-4-10)17(21)22/h1-8H,(H2,14,15,18)

HIDE SMILES / InChI

Molecular Formula C13H10N4O5
Molecular Weight 302.2423
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/vet/nicarb-25.html | https://www.drugs.com/vet/nicarb-can.html | https://www.ncbi.nlm.nih.gov/pubmed/1886867 | https://www.ncbi.nlm.nih.gov/pubmed/13843719

Nicarbazin, a complex of two compounds, 4,4'-dinitrocarbanilide (DNC) and 4,6-dimethyl-2-pyrimidinol (HDP) is an effective drug for preventing intestinal and caecal coccidiosis in poultry. It is used for prevention rather than the treatment of disease. Nicarbazin was the first agent with “broad‐spectrum” activity against Eimeria spp. of chickens. Nicarbazin is used as a single agent or in combination with polyether antibiotics (narasin, or maduramicin), roxarsone, or antibiotics (lincomycin, bacitracin, flavomycin) for prevention and control of coccidiosis caused by Eimeria spp. (all relevant species) in broiler chickens. Nicarbazin can cause increased sensitivity to heat stress, which may result in growth depression and even mortality in broilers; death may be due to cell degeneration processes in liver and kidneys; at the recommended dose, the drug causes occasionally toxic effects in laying hens like reduced hatchability and interruption of egg-laying. Nicarbazin interferes with the formation of the vitelline membrane, separating the egg yolk and egg white. The exact mode of action is unknown, although it is thought nicarbazin interferes with cholesterol metabolism in the formation of the membrane.

Originator

Sources: Poultry Sci. (Research Notes), Volume 34, Pages1164-5, Journal, 1955

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
NICARB

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The therapeutic effect of 16 antimicrobial agents on Cryptosporidium infection in mice.
1982 Apr
Patents

Patents

Sample Use Guides

Nicarbazin is added to chicken feed at a concentration of 113.5 g/ton as an aid in preventing outbreaks of cecal (Eimeria tenella) and intestinal (E. acervulina, E. maxima, E, necatrix, and E. brunetti) coccidiosis.
Route of Administration: Oral
In Vitro Use Guide
Fibroblasts were obtained by collagenase digestion from chicken skin and cultured. The cultured cells were incubated with various concentrations of nicarbazin (up to 1nM), and [3H]proline incorporation was evaluated in collagenase-digestible (representing mostly collagen) and nondigestible proteins exported by the cells into the medium.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:55:36 GMT 2023
Edited
by admin
on Fri Dec 15 18:55:36 GMT 2023
Record UNII
9IDD210E75
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4,4'-DINITROCARBANILIDE
MI  
Common Name English
CARBANILIDE, 4,4'-DINITRO-
Systematic Name English
NSC-101086
Code English
N,N'-BIS(4-NITROPHENYL)UREA
Systematic Name English
4-4'-DINITROCARBANALIDE
Common Name English
DNC
Common Name English
4,4'-DINITROCARBANILIDE [MI]
Common Name English
4,4'-DINITRODIPHENYLUREA
Common Name English
Code System Code Type Description
FDA UNII
9IDD210E75
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY
RXCUI
1546355
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY RxNorm
DAILYMED
9IDD210E75
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY
MESH
C039493
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID0043761
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
209-607-7
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY
NSC
101086
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY
PUBCHEM
9509
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY
MERCK INDEX
m4574
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY Merck Index
CAS
587-90-6
Created by admin on Fri Dec 15 18:55:36 GMT 2023 , Edited by admin on Fri Dec 15 18:55:36 GMT 2023
PRIMARY
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