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Details

Stereochemistry ACHIRAL
Molecular Formula C13H10N4O5.C6H8N2O
Molecular Weight 426.3828
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICARBAZIN

SMILES

CC1=CC(C)=NC(=O)N1.[O-][N+](=O)C2=CC=C(NC(=O)NC3=CC=C(C=C3)[N+]([O-])=O)C=C2

InChI

InChIKey=UKHWDRMMMYWSFL-UHFFFAOYSA-N
InChI=1S/C13H10N4O5.C6H8N2O/c18-13(14-9-1-5-11(6-2-9)16(19)20)15-10-3-7-12(8-4-10)17(21)22;1-4-3-5(2)8-6(9)7-4/h1-8H,(H2,14,15,18);3H,1-2H3,(H,7,8,9)

HIDE SMILES / InChI

Molecular Formula C6H8N2O
Molecular Weight 124.1405
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 15:10:43 UTC 2023
Edited
by admin
on Fri Dec 15 15:10:43 UTC 2023
Record UNII
11P9NUA12U
Record Status Validated (UNII)
Record Version
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Name Type Language
NICARBAZIN
GREEN BOOK   HSDB   MART.   MI  
Common Name English
NSC-7171
Code English
NICARBAZIN [MART.]
Common Name English
NICARBAZIN [HSDB]
Common Name English
NICARBAZIN [MI]
Common Name English
1,3-BIS(4-NITROPHENYL)UREA COMPLEX WITH 4,6-DIMETHYLPYRIMIDIN-2-OL
Common Name English
NICARBAZIN [GREEN BOOK]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 85712
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
NCI_THESAURUS C737
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
CFR 21 CFR 556.445
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
CFR 21 CFR 558.366
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
Code System Code Type Description
MESH
D009528
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
FDA UNII
11P9NUA12U
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-359-1
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
PUBCHEM
9507
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
HSDB
7466
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
MERCK INDEX
m7849
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
NICARBAZIN
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID6034762
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
DAILYMED
11P9NUA12U
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
NCI_THESAURUS
C76086
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
RXCUI
1311583
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY RxNorm
SMS_ID
300000029191
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
NSC
7171
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
CAS
330-95-0
Created by admin on Fri Dec 15 15:10:43 UTC 2023 , Edited by admin on Fri Dec 15 15:10:43 UTC 2023
PRIMARY
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ACTIVE MOIETY