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

ChemicalBook > CAS DataBase List > 2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide

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

Product Name: 2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide
CAS No.: 108605-62-5
Chemical Name: 2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide
Synonyms: Su 20;CS-862;Aubagio;Aids013145;Aids-013145;rac-A77 1626;Teriflunomide;(E/Z)-Teriflunomide;TeriflunoMide, A77 1726;Teriflunomide((E/Z) Mixture)
CBNumber: CB6464433
Molecular Formula: C12H9F3N2O2
Formula Weight: 270.21
MOL File: 108605-62-5.mol

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

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).
pka: 5.20±0.50(Predicted)
form: Solid
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.

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Safety

Hazard Codes: Xn
Risk Statements: 22
HS Code: 2926900005
Toxicity: mouse,LD50,intraperitoneal,100mg/kg (100mg/kg),United States Patent Document. Vol. #5494911,

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHR2878
Product name: Leflunomide Related Compound B
Purity: pharmaceutical secondary standard, certified reference material
Packaging: 50MG
Price: $634
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1357056
Product name: Leflunomide Related Compound B
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 20mg
Price: $1530
Updated: 2024/03/01

Tocris

Product number: 5069
Product name: Teriflunomide
Purity: ≥99%(HPLC)
Packaging: 50
Price: $151
Updated: 2021/12/16

TRC

Product number: A771720
Product name: A771726(E/Z)Mixture
Packaging: 50mg
Price: $80
Updated: 2021/12/16

Usbiological

Product number: 256904
Product name: Teriflunomide
Packaging: 50mg
Price: $389
Updated: 2021/12/16

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2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide Chemical Properties,Usage,Production

Description

Teriflunomide (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 Properties

White Solid

Uses

The 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.

Definition

ChEBI: 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 Use

Immunomodulating agent:
Treatment of relapsing remitting multiple sclerosis

Synthesis

Numerous 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.

Drug interactions

Potentially 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.

Metabolism

Teriflunomide 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.

storage

Store at +4°C

References

1) 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

Raw materials

Preparation Products

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

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View Lastest Price from 2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide manufacturers

Career Henan Chemical Co

Product: A77 1726 108605-62-5
Price: US $1.00/KG
Min. Order: 1G
Purity: 99%
Supply Ability: 100KG
Release date: 2018-08-13

108605-62-5, 2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amideRelated Search:

BESTATIN HYDROCHLORIDE Palmitoylethanolamide ALPHA-CYANO-4-HYDROXYCINNAMIC ACID Acetylcholine Glatiramer acetate Histamine DNA, SINGLE STRANDED, IMM. ON CELLULOSE, FROM CALF THYMUS* Pimecrolimus Bortezomib SB 415286 Anacetrapib Lacidipine Afatinib Olaparib 2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide CROTONAMIDE Teriflunomide-d4 2-CYANO-N-P-TOLYL-ACETAMIDE

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

Teriflunomide(Random Configuration)

(2Z)-2-[hydroxy-[4-(trifluoromethyl)anilino]methylidene]-3-oxobutanenitrile

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

CS-862

2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)cro

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

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

(E)-2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)-2-butenamide

2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-

Aids013145

Aids-013145

Su 20

Teriflunomide

(Z)-2-cyano-3-hydroxy-N-(4-(trifluoroMethyl)phenyl)but-2-enaMide

Leflunomide Related Compound B (10 mg) (2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide)

2-Cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide,teriflunomide

Leflunomide Related Compound B (20 mg) (2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide)

2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)-2-butenamid

n-(4-trifluoromethylphenyl)-2-cyano-2-hydroxycrotonamide

N-(4-TRIFLUOROMETHYLPHENYL)-2-CYANO-3-HYDROXYCROTOAMIDE

N-(4-TRIFLUOROMETHYLPHENYL)-2-CYANO-3-HYDROXYCROTONAMIDE

2-CYANO-3-OH-N-(4-TRIFLUOROMETHYLPHENYL) CROTONAMIDE

2-CYANO-3-HYDROXY-N-[4-(TRIFLUOROMETHYL)PHENYL]-2-BUTENAMIDE

rac-A77 1626

Leflunomide impurityⅡ[2-cyano-3-hydroxy-N-(4’-trifluoromethylphenyl)-crotone amide]

Aubagio

2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide USP/EP/BP

Teriflunomide((E/Z) Mixture)

Leflunomide USP Related Compound B

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

Leflunomide Related Compound B (2-Cyano-3-hydroxy-N-(4''-trifluoromethylphenyl)-crotone amide) (1357056)

Leflunomide impurityⅡ [2-cyano-3-hydroxy-N-(4’ -trifluoromethylphenyl)-croton e amide

(E/Z)-Teriflunomide

2-cyano-3-hydroxy-crotonic acid 4-trifluoro-methyl-anilide

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

108605-62-5

C12H5F3N2O2D4

Various Metabolites and Impurities

Metabolites & Impurities

Tyrosine Kinase Inhibitors