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2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide

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Company Name: Capot Chemical Co.,Ltd.
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Products Intro: Product Name:Teriflunomide
CAS:108605-62-5
Purity:98%(Min,HPLC) Package:100g;1kg;5kg,10kg,25kg,50kg
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Products Intro: Product Name:2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide
CAS:108605-62-5
Purity:99% Package:25KG;5KG;1KG
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Products Intro: CAS:108605-62-5
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Products Intro: Product Name:A77 1726
CAS:108605-62-5
Purity:98% HPLC Package:5MG;10MG;50MG;100MG,1G,5G
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Products Intro: Product Name:A77 1726
CAS:108605-62-5
Purity:99% Package:1KG;1USD

2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide manufacturers

  • TeriflunoMide, A77 1726
  • TeriflunoMide, A77 1726 pictures
  • $0.00 / 5mg
  • 2021-07-20
  • CAS:108605-62-5
  • Min. Order: 5mg
  • Purity: 99% HPLC
  • Supply Ability: 2000tons
  • A77 1726
  • A77 1726 pictures
  • $1.00 / 1KG
  • 2019-07-06
  • CAS:108605-62-5
  • Min. Order: 1G
  • Purity: 99%
  • Supply Ability: 100KG
2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide Basic information
Product Name:2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide
Synonyms:A77 1726;N-(4-Trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide, 2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-beuteamide, LEF-M;(2Z)-2-[hydroxy-[[4-(trifluoromethyl)phenyl]amino]methylidene]-3-oxo-butanenitrile;2-Cyano-3OH-N-(4-trifluoromethylphenyl) crotonamide-d4;IMp. A (EP) as Hydrochloride: 4-(TrifluoroMethyl)aniline Hydrochloride;TeriflunoMide, A77 1726;2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)crotonamide;2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
CAS:108605-62-5
MF:C12H9F3N2O2
MW:270.21
EINECS:1308068-626-2
Product Categories:Various Metabolites and Impurities;Metabolites & Impurities;Tyrosine Kinase Inhibitors
Mol File:108605-62-5.mol
2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide Structure
2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide Chemical Properties
Melting point 229-232°C
Boiling point 410.8±45.0 °C(Predicted)
density 1.424±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility Soluble in DMSO (up to 30 mg/ml), or in Ethanol (up to 5 mg/ml with warming).
pka5.20±0.50(Predicted)
color White
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
Safety Information
Hazard Codes Xn
Risk Statements 22
HS Code 2926900005
Toxicitymouse,LD50,intraperitoneal,100mg/kg (100mg/kg),United States Patent Document. Vol. #5494911,
MSDS Information
2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide Usage And Synthesis
DescriptionTeriflunomide (Aubagio®), also known as A77 1726, is an immunosupressant marketed by Sanofi for the teatment of multiple sclerosis (MS). Teriflunomide is the active metabolite of leflunomide, used for treatment of patients diagnosed with rheumatoid arthritis, and therefore simultaneously can be used as a treatment for rheumatoid arthritis.Teriflunomide acts as an inhibitor of the mitochondrial enzyme dihydrorotate dehydrogenase, inhibiting pyrimidine formation, and resulting in reduced B and T cell proliferation.
Chemical PropertiesWhite Solid
UsesThe active metabolite of Leflunomide, 2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide can be used as a potent disease-modifying antirheumatic drug used in the treatment of rheumatoid arthritis.
DefinitionChEBI: Teriflunomide is an enamide obtained by formal condensation of the carboxy group of (2Z)-2-cyano-3-hydroxybut-2-enoic acid with the anilino group of 4-(trifluoromethyl)aniline. Used for the treatment of relapsing forms of multiple sclerosis and rheumatoid arthritis. It has a role as an EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor, a tyrosine kinase inhibitor, a hepatotoxic agent, a drug metabolite and a non-steroidal anti-inflammatory drug. It is a nitrile, an enol, an aromatic amide, an enamide, a member of (trifluoromethyl)benzenes and a secondary carboxamide.
Clinical UseImmunomodulating agent:
Treatment of relapsing remitting multiple sclerosis
SynthesisNumerous syntheses of teriflunomide have been developed to date, most relying on the use of 4- trifluoromethyl aniline (167). The current optimized method for scale-up synthesis of teriflunomide, developed by Keshav and coworkers, begins with reaction of commercial 4-trifluoromethyl aniline 167 and ethylacetoacetate (168) in refluxing xylenes, providing acetoamidate 169 in 51% yield . The resulting acetoamidate 169 was then treated with H2O2, KBr, and concentrated HCl at room temperature, providing bromide 170 in 67% yield. Bromide 170 was reacted with NaCN in DMSO, generating teriflunomide (XXVI) in 85% yield.

Synthesis_108605-62-5

Drug interactionsPotentially hazardous interactions with other drugs
Lipid-lowering agents: effect significantly reduced by colestyramine - avoid; concentration of rosuvastatin increased - consider reducing rosuvastatin dose.
Live vaccines: risk of generalised infections - avoid.
MetabolismTeriflunomide is the active metabolite of leflunomide. It is moderately metabolised and teriflunomide is the only component detected in plasma. The main biotransformation pathway is hydrolysis with oxidation being a minor pathway. Secondary pathways involve oxidation, N-acetylation and sulfate conjugation. Teriflunomide is excreted in the gastrointestinal tract mainly through the bile as unchanged drug and most likely by direct secretion.
storageStore at +4°C
References1) Manna et al. (1999), Immunosuppressive leflunomide metabolite (A77 1726) blocks TNF-dependent nuclear factor-kappa B activation and gene expression; J. Immunol., 162 2095 2) Davis et al. (1996), immunosuppressive metabolite of leflunomide is a potent inhibitor of human dihydroorotate dehydrogenase; Biochemistry, 35 1270 3) Seah et al. (2008), Oxidative bioactivation and toxicity of leflunomide in immortalized human hepatocytes and kinetics of the non-enzymatic conversion to its major metabolite, A77 1726; Drug Metab. Lett., 2 153
2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide Preparation Products And Raw materials
Tag:2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide(108605-62-5) Related Product Information
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