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 9.2456642E11
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 1.17504003E12

PubMed

Title	Date	PubMed

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
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
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
Resistance to anticoccidial drugs of Dutch avian Eimeria spp. field isolates originating from 1996, 1999 and 2001.	2003 Aug	17585463
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
Control of coccidiosis in turkeys with diclazuril and monensin: effects upon performance and development of immunity to Eimeria species.	2004 Sep	15529986
Anticoccidial efficacy of drinking water soluble diclazuril on experimental and field coccidiosis in broiler chickens.	2005 Aug	16050910
[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
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
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
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
Actin-depolymerizing factor of second-generation merozoite in Eimeria tenella: clone, prokaryotic expression, and diclazuril-induced mRNA expression.	2010 Feb	20020308
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