69004-04-2

Basic information

• Product Name: Ponazuril
• Synonyms: Toltrazuril sulfone Ponazuril;1-Methyl-3-{3-methyl-4-[4-(trifluoromethylsulfonyl)phenoxy]phenyl}-1,3,5-triazine-2,4,6(1H,3H;Ponazuril;ToltrazurilSulfone;1-Methyl-3-{3-methyl-4-[4-(trifluoromethylsulfonyl)phenoxy]phenyl}-1,3,5-triazine-2,4,6(1H,3H,5H)-trione;Ponazuril [inn];Unii-jpw84as66u
• CAS NO: 69004-04-2
• Molecular Formula: C₁₈H₁₄F₃N₃O₆S
• Molecular Weight: 457.38
• EINECS: 1308068-626-2
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 69004-04-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 242°
• Appearance: /
• Density: 1.507 g/cm³
• Refractive Index: 1.572
• Storage Temp.: Refrigerator
• Solubility: Acetontrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 6.46±0.20(Predicted)
• CAS DataBase Reference: Ponazuril(CAS DataBase Reference)
• NIST Chemistry Reference: Ponazuril(69004-04-2)
• EPA Substance Registry System: Ponazuril(69004-04-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 69004-04-2(Hazardous Substances Data)

Usage

Description

Ponazuril is an active metabolite of the coccidiostat toltrazuril, which is used in the treatment of various protozoal infections. It is formed from toltrazuril via the intermediate metabolite toltrazuril sulfoxide by cytochrome P450 (CYP) enzymes, including CYP3A. Ponazuril exhibits potent antiprotozoal activity by inhibiting the production of tachyzoites in infected cells, thus preventing the spread of the infection.

Uses

Used in Veterinary Medicine:
Ponazuril is used as an antiprotozoal agent for the treatment of Equine Protozoal Myeloencephalitis (EPM) in horses. It effectively targets and eliminates the protozoal parasite responsible for EPM, leading to improved health and reduced neurological symptoms in affected horses.
Used in Human Medicine (Toxoplasmosis Treatment):
Ponazuril is also used as an antiprotozoal agent for the treatment of toxoplasmosis in humans. It is particularly effective in preventing infection with Toxoplasma gondii tachyzoites in mouse models of fatal toxoplasmosis when administered at appropriate doses. Additionally, it has been shown to reduce the number of infected individuals when administered following the onset of infection, highlighting its potential utility in both prophylactic and therapeutic settings.

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.

InChI:InChI=1/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)

Upstream product

• 432-84-8 4-Hydroxyphenyltrifluoromethylsulphone 

Relevant articles and documents

Preparation of ponazuril and toltrazuril

The invention relates to preparation of ponazuril and toltrazuril, in particular to a reaction of 1-(4-halogenated-3-methylphenyl)-3-methyl-1,3,5-triazine-2,4,6-trione and p-substituted phenol in thepresence of a copper catalyst/alkali/additive/solvent. The process is simple to operate and has an industrial large-scale production prospect.