DICLAZURIL

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 Search

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

Description
Sources: http://www.biovet.com/products/Anticoccidials/Clinacox.pdf
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

Targets

Primary Target	Pharmacology	Condition	Potency
Differentiation during parasite development 2 Target ID: Differentiation during parasite development Sources: http://www.biovet.com/products/Anticoccidials/Clinacox.pdf	Inhibitor 8504
Merozoite production 2 Target ID: Merozoite production Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=875c461a-e0db-4478-9006-7bd1d006ed3a	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Coccidiosis 45 Sources: http://www.biovet.com/products/Anticoccidials/Clinacox.pdf	Preventing		Approved 8583	CLINACOX Approved Use For the prevention of coccidiosis in animals. Launch Date 1999
Equine protozoal myeloencephalitis 3 Sources: https://merckusa.cvpservice.com/product/basic/view/1047490	Curative		Approved 8583	PROTAZIL Approved Use For the treatment of equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona. Launch Date 2007

PubMed

Title	Date	PubMed
Livestock drugs and disease: the fatal combination behind breeding failure in endangered bearded vultures.	2010-11-30	21152405
Pharmacokinetic and tissue distribution of doxycycline in broiler chickens pretreated with either: diclazuril or halofuginone.	2010-11	20736042
Eimeria tenella: effects of diclazuril treatment on microneme genes expression in second-generation merozoites and pathological changes of caeca in parasitized chickens.	2010-07	20138868
Multi-residue method for detecting coccidiostats at carry-over level in feed by HPLC-MS/MS.	2010-06	20198524
Histomorphometry and macroscopic intestinal lesions in broilers infected with Eimeria acervulina.	2010-03-25	20080348
Effects of diclazuril on apoptosis and mitochondrial transmembrane potential in second-generation merozoites of Eimeria tenella.	2010-03-25	20005046
Actin-depolymerizing factor of second-generation merozoite in Eimeria tenella: clone, prokaryotic expression, and diclazuril-induced mRNA expression.	2010-02	20020308
Multi-residue confirmatory method for the determination of twelve coccidiostats in chicken liver using liquid chromatography tandem mass spectrometry.	2009-11-13	19481216
Validation of a multi-residue liquid chromatography-tandem mass spectrometry confirmatory method for 10 anticoccidials in eggs according to Commission Decision 2002/657/EC.	2009-11-13	19442981
Sensitivity of isolates of Eimeria from turkey flocks to the anticoccidial drugs amprolium, clopidol, diclazuril, and monensin.	2009-09	19848080
Study of the comparative efficacy of toltrazuril and diclazuril against ovine coccidiosis in housed lambs.	2009-08	19575235
Genotype comparison of sorbitol-negative Escherichia coli isolates from healthy broiler chickens from different commercial farms.	2009-07	19531720
[Comparison of pretreatment methods for the simultaneous determination of diclazuril and toltrazuril residues in chicken tissues].	2009-05	19803134
Fast liquid chromatography/multiple-stage mass spectrometry of coccidiostats.	2009-05	19308967
Efficacy of toltrazuril (Baycox 5% suspension) in natural infections with pathogenic Eimeria spp. in housed lambs.	2009-04	19085006
Dietary supplementation of mannan-oligosaccharide enhances neonatal immune responses in chickens during natural exposure to Eimeria spp.	2009-03-19	19298670
Assessing the effect of diclazuril on the intestinal absorptive capacity of broilers infected with experimental coccidiosis, using d-xylose absorption test.	2008-06	18471149
Comparison of three adjuvants used to produce polyclonal antibodies to veterinary drugs.	2008-03-15	18063100
Effect of subcutaneously administered diclazuril on the output of Eimeria species oocysts by experimentally infected rabbits.	2008-02-02	18245747
The effect of a metaphylactic treatment with diclazuril (Vecoxan) on the oocyst excretion and growth performance of calves exposed to a natural Eimeria infection.	2007-11-10	17850970
Use of antigen mimics to produce specific antibodies to anti-coccidial drugs.	2007-05-31	17433817
Efficacy of some anticoccidial drugs for treating coccidial enteritis of the common carp caused by Goussia carpelli (Apicomplexa: Eimeriidae).	2007-03	17385557
Efficacy of various anticoccidials against experimental porcine neonatal isosporosis.	2007-01	17048000
The efficacy and economic benefits of Supercox, a live anticoccidial vaccine in a commercial trial in broiler chickens in China.	2006-11-30	16876953
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.	2006-09	17039846
Increased level of Eimeria sensitivity to diclazuril after using a live coccidial vaccine.	2006-09	17039828
New therapeutic approaches for equine protozoal myeloencephalitis: pharmacokinetics of diclazuril sodium salts in horses.	2006	16598684
Incidence of residues of nine anticoccidials in eggs.	2005-11	16332635
Deposition and depletion of five anticoccidials in eggs.	2005-09-07	16131122
Anticoccidial efficacy of drinking water soluble diclazuril on experimental and field coccidiosis in broiler chickens.	2005-08	16050910
Liquid chromatographic tandem mass spectrometric determination of five coccidiostats in poultry eggs and feed.	2005-06-25	15893963
[Comparison of the proteome of the sporutated oocysts of Eimeria tenella diclazuril sensitive strain with diclazuril resistant strain].	2005-05	16108370
Epidemiology of Eimeria infections in an Austrian milking sheep flock and control with diclazuril.	2005-04-20	15817196
Detection of residues of the coccidiostat diclazuril in poultry tissues by liquid chromatography-tandem mass spectrometry after withdrawal of medicated feed.	2005-02-23	15712996
Efficient and sensitive detection of residues of nine coccidiostats in egg and muscle by liquid chromatography-electrospray tandem mass spectrometry.	2004-12-25	15556532
Control of coccidiosis in turkeys with diclazuril and monensin: effects upon performance and development of immunity to Eimeria species.	2004-09	15529986
Effects of a herbal complex against Eimeria tenella infection in chickens.	2004-05	15228556
Histopathological observations on the activity of diclazuril (Vecoxan) against the endogenous stages of Eimeria crandallis in sheep.	2003-10-30	14580801
Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001.	2003-08	17585463
Studies on the efficacy of toltrazuril, diclazuril and sulphadimidine against artificial infections with Isospora suis in piglets.	2003-07	12928891
[Simple determination of residual anticoccidial drugs (diclazuril and nicarbazin) in chicken tissues by HPLC].	2003-04	12846158
The use of diclazuril in extended withdrawal anticoccidial programs: 2. Immunity to Eimeria tenella challenge after drug withdrawal.	2002-03	11902411
The use of diclazuril in extended withdrawal anticoccidial programs: 1. Efficacy against Eimeria spp. in broiler chickens in floor pens.	2002-03	11902410
Quantitative analysis of diclazuril in animal plasma by liquid chromatography/electrospray ionization mass spectrometry.	2002	12125023
Activity of toltrazuril and diclazuril against Isospora species in kittens and puppies.	2001-04-21	11345994
Efficacy of diclazuril in comparison with chemical and ionophorous anticoccidials against Eimeria spp. in broiler chickens in floor pens.	2001-04	11297280
Activity of diclazuril against Toxoplasma gondii in cultured cells and mice.	1994-04	8017699
Assessment of candidate anticryptosporidial agents in an immunosuppressed rat model.	1993-03	8440946
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.	1991-11-01	1818183
In vitro cultivation of Cryptosporidium parvum and screening for anticryptosporidial drugs.	1990-08	2221857

Patents

Sample Use Guides

In Vivo Use Guide

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

Name

Type

Language

DICLAZURIL FOR VETERINARY USE

Preferred Name

English

DICLAZURIL

Official Name

English

R-64433

Code

English

DICLAZURIL [USP MONOGRAPH]

Common Name

English

DICLAZURIL [GREEN BOOK]

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