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Details

Stereochemistry RACEMIC
Molecular Formula C17H9Cl3N4O2
Molecular Weight 407.638
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DICLAZURIL

SMILES

ClC1=CC=C(C=C1)C(C#N)C2=C(Cl)C=C(C=C2Cl)N3N=CC(=O)NC3=O

InChI

InChIKey=ZSZFUDFOPOMEET-UHFFFAOYSA-N
InChI=1S/C17H9Cl3N4O2/c18-10-3-1-9(2-4-10)12(7-21)16-13(19)5-11(6-14(16)20)24-17(26)23-15(25)8-22-24/h1-6,8,12H,(H,23,25,26)

HIDE SMILES / InChI
Molecular Formula C17H9Cl3N4O2
Molecular Weight 407.638
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including, https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=875c461a-e0db-4478-9006-7bd1d006ed3a

Diclazuril is a main component of veterinary drugs used for the treatment of coccidiosis (chickens, turkeys, rabbits, etc) and equine protozoal myeloencephalitis (horses). When used for the treatment of coccidiosis, it acts by causing the degeneration of schizonts and gamonts. While in the animals affected by protozoal myeloencephalitis the drug is believed to inhibit merozoite production. In vivo experiments on horses have shown that the drug may cross the blood brain barrier.

CNS Activity

Originator

Approval Year

2001
198
Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Differentiation during parasite development
Inhibitor
8228
Inhibitor
8228
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8360
CLINACOX

Approved Use

For the prevention of coccidiosis in animals.

Launch Date

9.2456642E11
Curative
Approved
8360
PROTAZIL

Approved Use

For the treatment of equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona.

Launch Date

1.17504003E12
PubMed

PubMed

TitleDatePubMed
In vitro quantitative analysis of (3)H-uracil incorporation by Sarcocytis neurona to determine efficacy of anti-protozoal agents.
2001 Feb 26
Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001.
2003 Aug
Efficient and sensitive detection of residues of nine coccidiostats in egg and muscle by liquid chromatography-electrospray tandem mass spectrometry.
2004 Dec 25
[Comparison of the proteome of the sporutated oocysts of Eimeria tenella diclazuril sensitive strain with diclazuril resistant strain].
2005 May
Deposition and depletion of five anticoccidials in eggs.
2005 Sep 7
The efficacy and economic benefits of Supercox, a live anticoccidial vaccine in a commercial trial in broiler chickens in China.
2006 Nov 30
Higher incidence of Eimeria spp. field isolates sensitive for diclazuril and monensin associated with the use of live coccidiosis vaccination with paracox-5 in broiler farms.
2006 Sep
Increased level of Eimeria sensitivity to diclazuril after using a live coccidial vaccine.
2006 Sep
New therapeutic approaches for equine protozoal myeloencephalitis: pharmacokinetics of diclazuril sodium salts in horses.
2006 Spring
Efficacy of some anticoccidial drugs for treating coccidial enteritis of the common carp caused by Goussia carpelli (Apicomplexa: Eimeriidae).
2007 Mar
Use of antigen mimics to produce specific antibodies to anti-coccidial drugs.
2007 May 31
The effect of a metaphylactic treatment with diclazuril (Vecoxan) on the oocyst excretion and growth performance of calves exposed to a natural Eimeria infection.
2007 Nov 10
Comparison of three adjuvants used to produce polyclonal antibodies to veterinary drugs.
2008 Mar 15
Study of the comparative efficacy of toltrazuril and diclazuril against ovine coccidiosis in housed lambs.
2009 Aug
[Comparison of pretreatment methods for the simultaneous determination of diclazuril and toltrazuril residues in chicken tissues].
2009 May
Fast liquid chromatography/multiple-stage mass spectrometry of coccidiostats.
2009 May
Multi-residue confirmatory method for the determination of twelve coccidiostats in chicken liver using liquid chromatography tandem mass spectrometry.
2009 Nov 13
Validation of a multi-residue liquid chromatography-tandem mass spectrometry confirmatory method for 10 anticoccidials in eggs according to Commission Decision 2002/657/EC.
2009 Nov 13
Sensitivity of isolates of Eimeria from turkey flocks to the anticoccidial drugs amprolium, clopidol, diclazuril, and monensin.
2009 Sep
Multi-residue method for detecting coccidiostats at carry-over level in feed by HPLC-MS/MS.
2010 Jun
Patents

Patents

04767760
2
04912106
3
05830893
3
05994355
2
20010005910
4
20020077437
3
JP2003527336A
18
JP2006520819A
15
JP4722360B2
18
JP4806121B2
3

Sample Use Guides

In Vivo Use Guide
Curator's Comment: http://www.accessdata.fda.gov/scripts/animaldrugsatfda/details.cfm?dn=141-268
Coccidiosis: Mix 200 gram of Clinacox 0.5% premix per ton of complete feed. Equine protozoal myeloencephalitis: 1 milligram per kilogram of body weight in the daily grain ration for 28 days
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:10:08 UTC 2023
Edited
by admin
on Thu Jul 06 02:10:08 UTC 2023
Record UNII
K110K1B1VE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DICLAZURIL
GREEN BOOK   INN   MART.   MI   USAN   USP   USP-RS  
INN   USAN  
Official Name English
R-64433
Code English
DICLAZURIL [USP MONOGRAPH]
Common Name English
DICLAZURIL [GREEN BOOK]
Common Name English
DICLAZURIL FOR VETERINARY USE
EP  
Common Name English
DICLAZURIL [USP-RS]
Common Name English
NSC-759642
Code English
DICLAZURIL [MART.]
Common Name English
R64,433
Code English
DICLAZURIL [MI]
Common Name English
BENZENEACETONITRILE, 2,6-DICHLORO-.ALPHA.-(4-CHLOROPHENYL)-4-(4,5-DIHYDRO-3,5-DIOXO-1,2,4-TRIAZIN-2(3H)-YL)-
Systematic Name English
R-64-433
Code English
P-64433
Code English
DICLAZURIL [USAN]
Common Name English
NUOQIU
Brand Name English
DICLAZURIL FOR VETERINARY USE [EP MONOGRAPH]
Common Name English
CLINACOX
Brand Name English
(P-CHLOROPHENYL)(2,6-DICHLORO-4-(4,5-DIHYDRO-3,5-DIOXO-AS-TRIAZIN-2(3H)-YL)PHENYL)ACETONITRILE
Common Name English
VECOXAN
Brand Name English
diclazuril [INN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.606
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
CFR 21 CFR 558.198
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
WHO-VATC QP51AJ03
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
NCI_THESAURUS C277
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
CFR 21 CFR 556.185
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
Code System Code Type Description
FDA UNII
K110K1B1VE
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
DAILYMED
K110K1B1VE
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
RXCUI
1368201
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY RxNorm
RS_ITEM_NUM
1188560
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
PUBCHEM
456389
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
MERCK INDEX
M4360
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL284733
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
INN
5971
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
USAN
Y-61
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
SMS_ID
100000082936
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
CAS
101831-37-2
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
NCI_THESAURUS
C76418
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
DRUG BANK
DB11398
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
WIKIPEDIA
DICLAZURIL
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
MESH
C057884
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
EVMPD
SUB07091MIG
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
NSC
759642
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID4046787
Created by admin on Thu Jul 06 02:10:08 UTC 2023 , Edited by admin on Thu Jul 06 02:10:08 UTC 2023
PRIMARY
Related Record Type Details
Structure of DICLAZURIL SODIUM
SALT/SOLVATE -> PARENT
Structure of DICLAZURIL, (R)-
ENANTIOMER -> RACEMATE
Structure of DICLAZURIL
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Structure of DICLAZURIL POTASSIUM
SALT/SOLVATE -> PARENT
Structure of DICLAZURIL
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Structure of DICLAZURIL, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of 2-(3,5-DICHLORO-4-((RS)-(4-CHLOROPHENYL)CYANOMETHYL)PHENYL)-3,5-DIOXO-2,3,4,5-TETRAHYDRO-1,2,4-TRIAZINE-6-CARBOXYLIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2-(3,5-DICHLORO-4-((4-CHLOROPHENYL)CYANOMETHYL)PHENYL)-3,5-DIOXO-2,3,4,5-TETRAHYDRO-1,2,4-TRIAZINE-6-CARBOXAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (4-AMINO-2,6-DICHLOROPHENYL)(4-CHLOROPHENYL)ACETONITRILE
IMPURITY -> PARENT
Specific limit is not given. Any other impurity-0.25% peak area.
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-(3,5-DICHLORO-4-(4-CHLOROBENZOYL)PHENYL)-1,2,4-TRIAZINE-3,5(2H,4H)-DIONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2-(3,5-DICHLORO-4-(4-CHLOROBENZYL)PHENYL)-1,2,4-TRIAZINE-3,5(2H,4H)-DIONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (4-AMINO-2,6-DICHLOROPHENYL)(4-CHLOROPHENYL)ACETONITRILE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 2-(3,5-DICHLORO-4-((RS)-(4-CHLOROPHENYL)CYANOMETHYL)PHENYL)-3,5-DIOXO-2,3,4,5-TETRAHYDRO-1,2,4-TRIAZINE-6-CARBOXYLIC ACID
IMPURITY -> PARENT
Specific limit is not given. Any other impurity - 0.25% peak area.
EP
Structure of N,2-BIS(3,5-DICHLORO-4-((4-CHLOROPHENYL)CYANOMETHYL)PHENYL)-3,5-DIOXO-2,3,4,5-TETRAHYDRO-1,2,4-TRIAZINE-6-CARBOXAMIDE
IMPURITY -> PARENT
Specific limit is not given. Any other impurity - 0.25% peak area.
EP
Structure of 2-(3,5-DICHLORO-4-(4-CHLOROBENZOYL)PHENYL)-1,2,4-TRIAZINE-3,5(2H,4H)-DIONE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.9
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (4-CHLOROPHENYL)(2,6-DICHLOROPHENYL)ACETONITRILE
IMPURITY -> PARENT
For the calculation of contents, multiply the peak areas by 1.4; Specific limit not given. Any other impurity-0.25% peak area.
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (2,6-DICHLORO-4-(3,5-DIOXO-4,5-DIHYDRO-1,2,4-TRIAZIN-2(3H)-YL)PHENYL)(4-HYDROXYPHENYL)ACETONITRILE
IMPURITY -> PARENT
Specific limit is not given. Any other impurity - 0.25% peak area.
EP
Structure of 2-(3,5-DICHLORO-4-(4-CHLOROBENZYL)PHENYL)-1,2,4-TRIAZINE-3,5(2H,4H)-DIONE
IMPURITY -> PARENT
Specific limit is not given. Any other impurity - 0.25% peak area.
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of BUTYL 2-(3,5-DICHLORO-4-((4-CHLOROPHENYL)CYANOMETHYL)PHENYL)-3,5-DIOXO-2,3,4,5-TETRAHYDRO-1,2,4-TRIAZINE-6-CARBOXYLATE
IMPURITY -> PARENT
Specific limit is not given. Any other impurity - 0.25% peak area.
EP
Structure of 2-(3,5-DICHLORO-4-((4-CHLOROPHENYL)CYANOMETHYL)PHENYL)-3,5-DIOXO-2,3,4,5-TETRAHYDRO-1,2,4-TRIAZINE-6-CARBOXAMIDE
IMPURITY -> PARENT
Specific limit is not given. Any other impurity - 0.25% peak area.
EP
Structure of (4-CHLOROPHENYL)(2,6-DICHLOROPHENYL)ACETONITRILE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of DICLAZURIL
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