Toltrazuril

Iupac Name：1-methyl-3-[3-methyl-4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]-1,3,5-triazinane-2,4,6-trione

Molecular Weight：425.382

Modify Date.: 2022-11-05 03:01

Introduction: Toltrazuril (Baycox®,Procox®) is a triazinon drug thathas broad-spectrum anticoccidial and antiprotozoalactivity. It is not commercially available in the UnitedStates, but it is available in other countries. It is activeagainst both asexual and sexual stages of coccidia byinhibiting nuclear division of schizonts and microga-monts and the wall-forming bodies of macrogamonts. Itmay also be useful in the treatment of neonatal porcinecoccidiosis, EPM, and canine hepatozoonosis. View more+

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1. Names and Identifiers

1.1 Name: Toltrazuril
1.2 Synonyms: 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1-methyl-3-[3-methyl-4-[4-[(trifluoromethyl)thio]phenoxy]phenyl]- 1-Methyl-3-(3-methyl-4-{4-[(trifluoromethyl)sulfanyl]phenoxy}phenyl)-1,3,5-triazinane-2,4,6-trione 1-methyl-3-[3-methyl-4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]-1,3,5-triazinane-2,4,6-trione 1-methyl-3-[3-methyl-4-[4-(trifluoromethylthio)phenoxy]phenyl]-1,3,5-triazinane-2,4,6-trione 1-Methyl-3-[3-methyl-4-[4-[(trifluoromethyl)thio]phenoxy]phenyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione 1-Methyl-3-[4-[p-[(trifluoromethyl)thio]phenoxy]-m-tolyl]-s-triazine-2,4,6(1H,3H,5H)-trione Bay Vi 9142 BAYCOX Baycox, 1-Methyl-3-{3-methyl-4-[4-(trifluoromethylthio)phenoxy]phenyl}-1,3,5-triazine-2,4,6(1H,3H,5H)-trione bay-i9142 C18H14F3N3O4S=425.4 EINECS 231-710-0 MFCD00867201 Toltrazuri

1.3 CAS No.: 69004-03-1

1.4 CID: 68591

1.5 EINECS(EC#): 614-893-5

1.6 Molecular Formula: C18H14F3N3O4S (isomer)

1.7 Inchi: InChI=1S/C18H14F3N3O4S/c1-10-9-11(24-16(26)22-15(25)23(2)17(24)27)3-8-14(10)28-12-4-6-13(7-5-12)29-18(19,20)21/h3-9H,1-2H3,(H,22,25,26)

1.8 InChkey: OCINXEZVIIVXFU-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=C(C=CC(=C1)N2C(=O)NC(=O)N(C2=O)C)OC3=CC=C(C=C3)SC(F)(F)F

1.10 Isomers Smiles: CC1=C(C=CC(=C1)N2C(=O)NC(=O)N(C2=O)C)OC3=CC=C(C=C3)SC(F)(F)F

2. Properties

2.1 Density: 1.54

2.1 Melting point: 192-196°C

2.1 Refractive index: 1.64

2.1 Precise Quality: 425.06600

2.1 PSA: 111.39000

2.1 logP: 2.93710

2.1 Appearance: Powder

2.2 Chemical Properties: Toltrazuril is white or off-white color crystalline powder, and odorless is molten in the methanol part omitted at ethyl acetate, dichloromethane, Polyethylene Glycol, α-adjoin in the organic solvents such as pyrrolidone, propylene glycol and dissolve, and is insoluble in water.Toltrazuril is an antiprotozoal agent that is widely used to prevent coccidia parasite infection in veterinary applications. The effectiveness of treatment appears to depend on the coccidian species, development stage of the parasite, and level of infection.

2.3 Color/Form: Powder

2.4 pKa: 6.47±0.20(Predicted)

2.5 Water Solubility: Insoluble

2.6 StorageTemp: Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Environmental Fate: The metabolite of toltrazuril, toltrazuril sulfone (ponazuril) is a persistent (half-life >1 year) and mobile compound and has adverse effects on both the growth and emergence of plants. Given the persistent properties of ponazuril repeated spreading of manure from treated animals may lead to an accumulation in the soil and consequently a risk to plants. The accumulation of ponazuril in soil together with its mobility also leads to a risk of leaching to groundwater. ToltrazurilSupplier

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 50 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (36%): Harmful if swallowed [Warning Acute toxicity, oral]
H400 (96%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P270, P273, P301+P312, P330, P391, and P501

3.3 Usage: tranquilizer

4. Safety and Handling

4.1 Symbol: GHS09

4.1 Hazard Codes: N

4.1 Signal Word: Warning

4.1 Risk Statements: R50/53

4.1 Safety Statements: S60;S61

4.1 Hazard Declaration: H410

4.1 RIDADR: UN 3077

4.1 Caution Statement: P273-P501

4.1 WGK Germany: 2

4.1 Safety: The Hazard Codes of?Toltrazuril (CAS NO.69004-03-1):?N,?Xi
The Risk Statements:
36/37/38:? Irritating to eyes, respiratory system and skin?
50/53:? Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment?
The Safety Statements:
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
60:? This material and/or its container must be disposed of as hazardous waste?
61:? Avoid release to the environment. Refer to special instructions safety data sheet?
37/39:? Wear suitable gloves and eye/face protection?
RIDADR: UN 3077

4.2 Specification: ? Toltrazuril , with CAS number of 69004-03-1, can be called 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1-methyl-3-(3-methyl-4-(4-((trifluoromethyl)thio)phenoxy)phenyl)- ; 1-Methyl-3-(4-(p-((trifluoromethyl)thio)phenoxy)-m-tolyl)-s-
triazine-2,4,6(1H,3H,5H)-trione . Toltrazuril (CAS NO.69004-03-1) is a coccidiostat.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P273 Avoid release to the environment.
Response	P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

69004-03-1Total: 2 Synthesis Route

106310-18-3

105-58-8 157 Suppliers

69004-03-1 304 Suppliers

Literatures:
US4874860 A1, ; US4898979 A1, ;
Yield: null

106310-17-2 1 Suppliers

105-58-8 157 Suppliers

69004-03-1 304 Suppliers

Literatures:
US4874860 A1, ; US4898979 A1, ;
Yield: null

8. Precursor and Product

precursor:

106310-17-2

105-58-8

106310-18-3

9. Other Information

9.0 Description: Toltrazuril (Baycox?,Procox?) is a triazinon drug thathas broad-spectrum anticoccidial and antiprotozoalactivity. It is not commercially available in the UnitedStates, but it is available in other countries. It is activeagainst both asexual and sexual stages of coccidia byinhibiting nuclear division of schizonts and microga-monts and the wall-forming bodies of macrogamonts. Itmay also be useful in the treatment of neonatal porcinecoccidiosis, EPM, and canine hepatozoonosis.

Toltrazuril and its major metabolite ponazuril (toltrazuril sulfone, Marquis) are triazine-based antiprotozoal drugs that have specific activity against apicomplexan coccidial infections. Toltrazuril is not available within the United States.

9.1 Chemical Properties: Toltrazuril is white or off-white color crystalline powder, and odorless is molten in the methanol part omitted at ethyl acetate, dichloromethane, Polyethylene Glycol, α-adjoin in the organic solvents such as pyrrolidone, propylene glycol and dissolve, and is insoluble in water.
Toltrazuril is an antiprotozoal agent that is widely used to prevent coccidia parasite infection in veterinary applications. The effectiveness of treatment appears to depend on the coccidian species, development stage of the parasite, and level of infection.

9.2 Uses: tranquilizer

9.3 Uses: Labelled analog of a triazinetrione anticoccidial. Coccidiostat. Toltrazuril is found to be highly effective against coccidia and is used in controlling coccidiosis. It is acting against all intracellular development stages of coccidia of the merogony (asexual multiplication) and gamogony (sexual phase). All stages are destroyed, thus the mode of action is coccidiocidal.

9.4 Clinical Use: Swine: Toltrazuril has been shown to reduce the signs of coccidiosis in naturally infected nursing pigs when a single oral 20–30 mg/kg BWdose is given to 3 to 6-dayold pigs (Driesen et al., 1995). Clinical signs were reduced from 71 to 22% of nursing pigs, and diarrhea and oocyst excretion were also decreased by the single oral treatment. Approved products carry a 77-daywithdrawal time in the United Kingdom.
Calves and lambs: Toltrazuril is used for the prevention of clinical signs of coccidiosis and reduction of coccidia shedding in calves and lambs as a single dose treatment. Withdrawal times in the United Kingdom are 63 and 42 days for calves and lambs, respectively.
Dogs: For hepatozoonosis, toltrazuril given orally at 5 mg/kg BW every 12 hours for 5 days or given orally at 10 mg/kg BW every 12 hours for 10 days caused remission of clinical signs in naturally infected dogs in 2–3 days (Macintire et al., 2001). Unfortunately, most treated dogs relapsed and eventually died from hepatozoonosis. In puppies with Isospora sp. infection, treatment with 0.45 mg emodepside in combination with 9 mg/kg BW toltrazuril (Procox?, Bayer Animal Health) reduces fecal oocyst count by 91.5–100%. There was no difference in duration of diarrhea when treatment was begun after the onset of clinical signs during patent infection (Altreuther et al., 2011).
Cats: In kittens experimentally infected with Isospora spp., treatment with a single oral dose of 0.9 mg emodepside in combination with 18 mg/kg BW toltrazuril (Procox?, Bayer AnimalHealth) reduces oocyst shedding by 96.7–100% if given during the prepatent period (Petry et al., 2011).
Horses: Toltrazuril has also been used for the treatment of EPM. This drug is safe, even at high doses. Current recommended treatments are 5–10 mg/kg orally for 28 days. Despite the favorable efficacy with toltrazuril, its use has diminished in horses because of better availability of other effective drugs.

9.5 Veterinary Drugs and Treatments: Toltrazuril is an antiprotozoal agent that may be considered as an alternative treatment for coccidiosis in dogs and cats, Hepatazoon infections, or for treating the oocyst shedding stage of toxoplasmosis in cats. It has also been used as a treatment for overwhelming parasitic loads in lizards (Bearded Dragons).
Toltrazuril has activity against parasites of the genus Hepatozoon, but other drugs (e.g., imidocarb, primaquine, doxycycline) are generally used.
While toltrazuril has been used to treat equine protozoal myeloencephalitis (EPM) caused by Sarcocystis neurona, use of approved products now available (e.g., nitazoxanide, ponazuril, pyrimethamine/ sulfadiazine) is preferred.
Toltrazuril has been used in some countries to treat Isospora suis in piglets.

9.6 Environmental Fate: The metabolite of toltrazuril, toltrazuril sulfone (ponazuril) is a persistent (half-life >1 year) and mobile compound and has adverse effects on both the growth and emergence of plants. Given the persistent properties of ponazuril repeated spreading of manure from treated animals may lead to an accumulation in the soil and consequently a risk to plants. The accumulation of ponazuril in soil together with its mobility also leads to a risk of leaching to groundwater.

10. Computational chemical data

Molecular Weight: 425.382g/mol
Molecular Formula: C₁₈H₁₄F₃N₃O₄S
Compound Is Canonicalized: True
XLogP3-AA: 4.4
Exact Mass: 425.06571160
Monoisotopic Mass: 425.06571160
Complexity: 655
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 8
Topological Polar Surface Area: 104
Heavy Atom Count: 29
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccB7OYBAAAAAAAAAAAAAAAAAAAAAAAA8YIAAAAAAAAABQAAAHwQQAAAADAyB2BQzx4PABAiIAiRCUACCCAAhKhAIiBgObIiMJiLksZuGOCjsxzNI6CewwCAOAMAAQAAIAAABgACAABAAAAAAAAAAAA==

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