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 8297
Merozoite production 2 Target ID: Merozoite production Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=875c461a-e0db-4478-9006-7bd1d006ed3a	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Coccidiosis 45 Sources: http://www.biovet.com/products/Anticoccidials/Clinacox.pdf	Preventing		Approved 8429	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 8429	PROTAZIL Approved Use For the treatment of equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona. Launch Date 2007

PubMed

Title	Date	PubMed
In vitro cultivation of Cryptosporidium parvum and screening for anticryptosporidial drugs.	1990 Aug	2221857
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.	1991 Nov-Dec	1818183
Assessment of candidate anticryptosporidial agents in an immunosuppressed rat model.	1993 Mar	8440946
Activity of diclazuril against Toxoplasma gondii in cultured cells and mice.	1994 Apr	8017699
Efficacy of diclazuril in comparison with chemical and ionophorous anticoccidials against Eimeria spp. in broiler chickens in floor pens.	2001 Apr	11297280
Activity of toltrazuril and diclazuril against Isospora species in kittens and puppies.	2001 Apr 21	11345994
In vitro quantitative analysis of (3)H-uracil incorporation by Sarcocytis neurona to determine efficacy of anti-protozoal agents.	2001 Feb 26	11223204
Diclazuril preventive therapy of gamma interferon knockout mice fed Sarcocystis neurona sporocysts.	2001 Jan 20	11137273
Quantitative analysis of diclazuril in animal plasma by liquid chromatography/electrospray ionization mass spectrometry.	2002	12125023
The use of diclazuril in extended withdrawal anticoccidial programs: 2. Immunity to Eimeria tenella challenge after drug withdrawal.	2002 Mar	11902411
The use of diclazuril in extended withdrawal anticoccidial programs: 1. Efficacy against Eimeria spp. in broiler chickens in floor pens.	2002 Mar	11902410
[Simple determination of residual anticoccidial drugs (diclazuril and nicarbazin) in chicken tissues by HPLC].	2003 Apr	12846158
Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001.	2003 Aug	17585463
Studies on the efficacy of toltrazuril, diclazuril and sulphadimidine against artificial infections with Isospora suis in piglets.	2003 Jul	12928891
Histopathological observations on the activity of diclazuril (Vecoxan) against the endogenous stages of Eimeria crandallis in sheep.	2003 Oct 30	14580801
Efficient and sensitive detection of residues of nine coccidiostats in egg and muscle by liquid chromatography-electrospray tandem mass spectrometry.	2004 Dec 25	15556532
Effects of a herbal complex against Eimeria tenella infection in chickens.	2004 May	15228556
Control of coccidiosis in turkeys with diclazuril and monensin: effects upon performance and development of immunity to Eimeria species.	2004 Sep	15529986
Epidemiology of Eimeria infections in an Austrian milking sheep flock and control with diclazuril.	2005 Apr 20	15817196
Detection of residues of the coccidiostat diclazuril in poultry tissues by liquid chromatography-tandem mass spectrometry after withdrawal of medicated feed.	2005 Feb 23	15712996
[Comparison of the proteome of the sporutated oocysts of Eimeria tenella diclazuril sensitive strain with diclazuril resistant strain].	2005 May	16108370
Incidence of residues of nine anticoccidials in eggs.	2005 Nov	16332635
Deposition and depletion of five anticoccidials in eggs.	2005 Sep 7	16131122
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	17039846
New therapeutic approaches for equine protozoal myeloencephalitis: pharmacokinetics of diclazuril sodium salts in horses.	2006 Spring	16598684
Efficacy of various anticoccidials against experimental porcine neonatal isosporosis.	2007 Jan	17048000
Efficacy of some anticoccidial drugs for treating coccidial enteritis of the common carp caused by Goussia carpelli (Apicomplexa: Eimeriidae).	2007 Mar	17385557
Use of antigen mimics to produce specific antibodies to anti-coccidial drugs.	2007 May 31	17433817
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	17850970
Effect of subcutaneously administered diclazuril on the output of Eimeria species oocysts by experimentally infected rabbits.	2008 Feb 2	18245747
Assessing the effect of diclazuril on the intestinal absorptive capacity of broilers infected with experimental coccidiosis, using d-xylose absorption test.	2008 Jun	18471149
Comparison of three adjuvants used to produce polyclonal antibodies to veterinary drugs.	2008 Mar 15	18063100
Efficacy of toltrazuril (Baycox 5% suspension) in natural infections with pathogenic Eimeria spp. in housed lambs.	2009 Apr	19085006
Study of the comparative efficacy of toltrazuril and diclazuril against ovine coccidiosis in housed lambs.	2009 Aug	19575235
Genotype comparison of sorbitol-negative Escherichia coli isolates from healthy broiler chickens from different commercial farms.	2009 Jul	19531720
Dietary supplementation of mannan-oligosaccharide enhances neonatal immune responses in chickens during natural exposure to Eimeria spp.	2009 Mar 19	19298670
[Comparison of pretreatment methods for the simultaneous determination of diclazuril and toltrazuril residues in chicken tissues].	2009 May	19803134
Fast liquid chromatography/multiple-stage mass spectrometry of coccidiostats.	2009 May	19308967
Multi-residue confirmatory method for the determination of twelve coccidiostats in chicken liver using liquid chromatography tandem mass spectrometry.	2009 Nov 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 Nov 13	19442981
Sensitivity of isolates of Eimeria from turkey flocks to the anticoccidial drugs amprolium, clopidol, diclazuril, and monensin.	2009 Sep	19848080
Actin-depolymerizing factor of second-generation merozoite in Eimeria tenella: clone, prokaryotic expression, and diclazuril-induced mRNA expression.	2010 Feb	20020308
Eimeria tenella: effects of diclazuril treatment on microneme genes expression in second-generation merozoites and pathological changes of caeca in parasitized chickens.	2010 Jul	20138868
Multi-residue method for detecting coccidiostats at carry-over level in feed by HPLC-MS/MS.	2010 Jun	20198524
Histomorphometry and macroscopic intestinal lesions in broilers infected with Eimeria acervulina.	2010 Mar 25	20080348
Effects of diclazuril on apoptosis and mitochondrial transmembrane potential in second-generation merozoites of Eimeria tenella.	2010 Mar 25	20005046
Pharmacokinetic and tissue distribution of doxycycline in broiler chickens pretreated with either: diclazuril or halofuginone.	2010 Nov	20736042
Livestock drugs and disease: the fatal combination behind breeding failure in endangered bearded vultures.	2010 Nov 30	21152405

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

Official Name

English

R-64433

Code

English

DICLAZURIL [USP MONOGRAPH]

Common Name

English

DICLAZURIL [GREEN BOOK]

Common Name

English

DICLAZURIL FOR VETERINARY USE

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