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101831-37-2

101831-37-2 Structure

101831-37-2 Structure
IdentificationMore
[Name]

Diclazuril
[CAS]

101831-37-2
[Synonyms]

2,6-DICHLORO-A-(4-CHLOROPHENYL)-4(4,5-DIHYDRO-3,5-DIOXO-1,2,4-TRIAZIN-2-YL)BENZENEACETONITRILE
2,6-DICHLORO-ALPHA-(4-CHLOROPHENYL)-4-(4,5-DIHYDRO-3,5-DIOXO-1,2,4-TRIAZIN-2 (3H)-YL)BENZENEACETONITRILE
2,6-dichloro-alpha-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3h)-yl)benzeneacetonitrile
CLINACOX
DICLAZURIL
DICLAZUTIL
clinazox
R-64433
Diclazuril premix 0.5%,1%
Diclazuril 0.5% 1% premix
Qiujia
DiclazurilCpv2000
2,6-dichloro-α-(4-chlorophenyl)-4-[4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3h)-yl]benzeneacetonitrile
2,6-Dichloro-alpha-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetonitrile
2,6-Dichloro-a-(4-chlorophenyl)-4-[4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl]benzeneacetonitrile
Nuoqiu
Vecoxan
2-[3,5-Dichloro-4-(α-cyano-4-chlorobenzyl)phenyl]-1,2,4-triazine-3,5(2H,4H)-dione
2-[4-(4-Chloro-α-cyanobenzyl)-3,5-dichlorophenyl]-1,2,4-triazine-3,5(2H,4H)-dione
[EINECS(EC#)]

1806241-263-5
[Molecular Formula]

C17H9Cl3N4O2
[MDL Number]

MFCD00867203
[Molecular Weight]

407.64
[MOL File]

101831-37-2.mol
Questions And AnswerBack Directory
[Preparation]

Using methanol as a solvent, 2,6-dichloro-α-(4-chlorophenyl)-4-nitrophenylacetonitrile (A) was hydrogenated and reduced to 4-amino-2,6-dichloro-α-(4-chlorophenyl)phenylacetonitrile (B) under 5% platinum-carbon catalysis. (B) underwent diazotization and coupling reactions to generate ethyl 2-[[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-hydrazine]-2-cyanoacetylcarbamate (C). (C) underwent cyclization and hydrolysis to generate 2-[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-2,3,4,5-tetrahydro-3,5-dicarbonyl-1,2,4-triazine-6-carboxylic acid (D). Using mercaptoacetic acid as a solvent, (D) underwent decarboxylation at 170°C to generate diclazuril. The cyclization and hydrolysis process is as follows: 7.8 parts of compound (C), 1.98 parts of anhydrous potassium acetate and 120 parts of glacial acetic acid are stirred and refluxed for 3 hours. After adding an appropriate amount of glacial acetic acid and 30 parts of concentrated hydrochloric acid, the mixture is stirred and refluxed for another 10 hours. Then, the mixture is concentrated, cooled and filtered, and the filter cake is compound (D).
[Description]

Diclazuril (molecular formula: C17H9Cl3N4O2, Trade name: Vecoxan) belongs to a kind of coccidiostat and potent antiprotozoal agents. It is mainly used for the treatment, control, prevention and improvements of Coccidal infections. It alleviates the symptoms of the patients by interrupting the life cycle of the parasites. It induces the morphological changes and attenuates the mitochondrial transmembrane potential in meroites. It can prevent congenital toxoplasmosis and have anticoccidial effects in vivo. It is active through oral administration.  
[References]

http://www.tabletwise.com/medicine/diclazuril
https://en.wikipedia.org/wiki/Diclazuril
http://www.abcam.com/diclazuril-ab143604.html
Chemical PropertiesBack Directory
[Melting point ]

290.5°
[density ]

1.56±0.1 g/cm3(Predicted)
[storage temp. ]

0-6°C
[solubility ]

DMF: 5mg/mL; DMSO: 5mg/mL; DMSO:PBS (pH 7.2) (1:5): 0.16mg/mL
[form ]

neat
[pka]

5.89±0.20(Predicted)
[color ]

White to Light yellow to Light orange
[Merck ]

14,3080
[Major Application]

forensics and toxicology
pharmaceutical (small molecule)
[InChI]

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)
[InChIKey]

ZSZFUDFOPOMEET-UHFFFAOYSA-N
[SMILES]

C1(C=C(C(C(C#N)C2=CC=C(Cl)C=C2)=C(Cl)C=1)Cl)N1N=CC(=O)NC1=O
[LogP]

2.439 (est)
[CAS DataBase Reference]

101831-37-2(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Health Hazard (GHS08)
GHS08
[Signal word ]

Warning
[Hazard statements ]

H361d-H373
[Precautionary statements ]

P202-P260-P280-P308+P313-P405-P501
[Safety Statements ]

24/25
[WGK Germany ]

2
[RTECS ]

CY1697600
[HS Code ]

29336990
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Repr. 2
STOT RE 2
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2,6-Dichloro-alpha-(4-chlorophenyl)-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)benzeneacetonitrile(101831-37-2).msds
Hazard InformationBack Directory
[Chemical Properties]

Off-White Solid
[Uses]

antiprotozoal
[Uses]

Nucleotide analog with broad-spectrum anticoccidial activity. Coccidiostat.
[Application]

Diclazuril(101831-37-2) is a less toxic, orally administered triazine antiprotozoal. It is widely used in veterinary medicine as a feed additive and veterinary drug. It is registered for oral use in broilers and lambs. Its use in cats (one dose of 25 mg/kg BW) is off-label only. It may be used clinically for the treatment of bovine protozoa. It is also used for the treatment of equine protozoan spinal cord encephalitis (EPM) caused by neuronal sarcocysts.
[Definition]

ChEBI: 2-(4-chlorophenyl)-2-[2,6-dichloro-4-(3,5-dioxo-1,2,4-triazin-2-yl)phenyl]acetonitrile is a nitrile.
[Veterinary Drugs and Treatments]

Diclazuril is indicated for the treatment of equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona and as a coccidiostat in broiler chickens.
Diclazuril could potentially be useful in treating coccidiosis, Neospora caninum and Toxoplasma infections in dogs or cats.
[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

Diclazuril(101831-37-2)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

101831-37-2(sigmaaldrich)
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