ChemicalBook Product Catalog Chemical Reagents Organic reagents Sulfone, sulfoxide compound Ponazuril

Ponazuril

Product NamePonazuril
CAS69004-04-2
MFC18H14F3N3O6S
MW457.38
EINECS629-740-8
MOL File69004-04-2.mol

Chemical Properties

Melting point	242°
Density	1.507±0.06 g/cm3(Predicted)
storage temp.	Refrigerator
solubility	Acetontrile (Slightly), DMSO (Slightly), Methanol (Slightly)
pka	6.46±0.20(Predicted)
form	Solid
color	White to Off-White
Major Application	forensics and toxicology pharmaceutical (small molecule) veterinary
InChI	InChI=1S/C18H14F3N3O6S/c1-10-9-11(24-16(26)22-15(25)23(2)17(24)27)3-8-14(10)30-12-4-6-13(7-5-12)31(28,29)18(19,20)21/h3-9H,1-2H3,(H,22,25,26)
InChIKey	VBUNOIXRZNJNAD-UHFFFAOYSA-N
SMILES	N1(C)C(=O)NC(=O)N(C2=CC=C(OC3=CC=C(S(C(F)(F)F)(=O)=O)C=C3)C(C)=C2)C1=O
CAS DataBase Reference	69004-04-2

Safety Information

WGK Germany	3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

Toltrazuril sulfone is an active metabolite of the coccidiostat toltrazuril . Toltrazuril sulfone is formed from toltrazuril via the intermediate metabolite toltrazuril sulfoxide by cytochrome P450 (CYP) enzymes, including CYP3A. It inhibits T. gondii tachyzoite production in African green monkey kidney cells when used at concentrations of 0.1, 1, and 5 μg/ml. Toltrazuril sulfone completely prevents infection with T. gondii tachyzoites in a mouse model of fatal toxoplasmosis when administered at doses of 10 or 20 mg/kg one day prior to, and daily for 10 days following, infection. It also reduces the number of infected mice in the same model when administered at a dose of 10 mg/kg for 11 days starting six days following infection. Formulations containing toltrazuril sulfone have been used in the treatment of equine protozoal myeloencephalitis (EPM) in horses.

Uses

Toltrazuril sulfone is antiprotazoal, used to treat Equine Protozoal Myeloencephalitis (EPM).

Veterinary Drugs and Treatments

Ponazuril is indicated for the treatment of equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona.
Ponazuril could potentially be useful in treating Neospora caninum and Toxoplasma infections in dogs or cats.

in vivo

Toltrazuril sulfone (10-20 mg/kg; p.o.; daily; for 10 days) is effective in preventing and treating toxoplasmosis in mice^[2].

Animal Model:	Female CD-1 mice^[2]
Dosage:	10 mg/kg, 20 mg/kg
Administration:	Oral administration, daily, for 10 days
Result:	Prevented and protected mice from toxoplasmosis.

IC 50

Coccidia

References

[1] ETIENNE BENOIT. Stereoselective S-oxygenation of an aryl-trifluoromethyl sulfoxide to the corresponding sulfone by rat liver cytochromes P450[J]. Biochemical pharmacology, 1993, 46 12: Pages 2337-2341. DOI: 10.1016/0006-2952(93)90626-8
[2] SHEILA M MITCHELL. Efficacy of ponazuril in vitro and in preventing and treating Toxoplasma gondii infections in mice.[J]. Journal of Parasitology, 2004, 90 3: 639-642. DOI: 10.1645/ge-250r

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