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

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

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

Molecular Weight:: 270.21

MDL Number:: MFCD00910058

MOL File:: 108605-62-5.mol

Last updated:2026-01-24 17:36:03

Product description	Number	Pack Size	Price
Leflunomide Related Compound B pharmaceutical secondary standard, certified reference material	PHR2878	50MG	$619.4
Leflunomide Related Compound B United States Pharmacopeia (USP) Reference Standard	1357056	20mg	$1330
Teriflunomide ≥99%(HPLC)	5069	50	$151
A771726(E/Z)Mixture	A771720	50mg	$80
Teriflunomide	256904	50mg	$389
More product size

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2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide 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).
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.
Major Application	pharmaceutical
InChI	1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-
InChIKey	UTNUDOFZCWSZMS-YFHOEESVSA-N
SMILES	O=C(/C(C#N)=C(O)/C)NC1=CC=C(C(F)(F)F)C=C1
FDA UNII	1C058IKG3B
ATC code	L04AA31
UNSPSC Code	41116107
NACRES	NA.24

Pharmacokinetic data

Protein binding	>99%
Excreted unchanged in urine	22.6 (as metabolites)
Volume of distribution	11 Litres
Biological half-life	18-19 days / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS06
Signal word	Danger
Hazard statements	H301
Precautionary statements	P264-P270-P301+P310-P405-P501
Hazard Codes	Xn
Risk Statements	22
WGK Germany	WGK 3
HS Code	2926900005
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral
Toxicity	mouse,LD50,intraperitoneal,100mg/kg (100mg/kg),United States Patent Document. Vol. #5494911,

2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide price More Price(28)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	PHR2878	Leflunomide Related Compound B pharmaceutical secondary standard, certified reference material	108605-62-5	50MG	$619.4	2025-07-31	Buy
Sigma-Aldrich	1357056	Leflunomide Related Compound B United States Pharmacopeia (USP) Reference Standard	108605-62-5	20mg	$1330	2025-07-31	Buy
Tocris	5069	Teriflunomide ≥99%(HPLC)	108605-62-5	50	$151	2021-12-16	Buy
TRC	A771720	A771726(E/Z)Mixture	108605-62-5	50mg	$80	2021-12-16	Buy
Usbiological	256904	Teriflunomide	108605-62-5	50mg	$389	2021-12-16	Buy

Product number	Packaging	Price	Buy
PHR2878	50MG	$619.4	Buy
1357056	20mg	$1330	Buy
5069	50	$151	Buy
A771720	50mg	$80	Buy
256904	50mg	$389	Buy

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

Synthesis_108605-62-5

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] S. MANNA B A. Immunosuppressive leflunomide metabolite (A77 1726) blocks TNF-dependent nuclear factor-kappa B activation and gene expression.[J]. Journal of immunology, 1999, 162 4 1: 2095-2102. DOI:10.4049/jimmunol.162.4.2095
[2] JUNE P. DAVIS. The Immunosuppressive Metabolite of Leflunomide Is a Potent Inhibitor of Human Dihydroorotate Dehydrogenase[J]. Biochemistry Biochemistry, 1996, 35 4: 1270-1273. DOI:10.1021/bi952168g
[3] QUEE MING SEAH. Oxidative bioactivation and toxicity of leflunomide in immortalized human hepatocytes and kinetics of the non-enzymatic conversion to its major metabolite, A77 1726.[J]. Drug metabolism letters, 2008, 2 3: 153-157. DOI:10.2174/187231208785425791

2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide Preparation Products And Raw materials

Raw materials

Preparation Products

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

Global( 193)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Capot Chemical Co.,Ltd.	+86-（0）57185586718; +8613336195806	sales@capot.com	China	29735	60
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21599	55
Nanjing ChemLin Chemical Industry Co., Ltd.	025-83697070	product@chemlin.com.cn	CHINA	3009	60
ATK CHEMICAL COMPANY LIMITED	+undefined-21-51877795	ivan@atkchemical.com	China	33024	60
career henan chemical co	+86-0371-86658258 +8613203830695	sales@coreychem.com	China	29833	58
TargetMol Chemicals Inc.	+1-781-999-5354; +17819995354	marketing@targetmol.com	United States	32470	58
HANGZHOU CLAP TECHNOLOGY CO.,LTD	86-571-88216897,88216896 13588875226	sales@hzclap.com	CHINA	6312	58
Xi'an MC Biotech, Co., Ltd.	029-89275612 +8618991951683	mcbio_sales@163.com	China	2251	58
RongNa Biotechnology Co.,Ltd	+86-86-13583358881 +8618560316533	Brad@rongnabiotech.com	China	3388	58
Dideu Industries Group Limited	+86-29-89586680 +86-15129568250	1026@dideu.com	China	19781	58

Supplier	Advantage
Capot Chemical Co.,Ltd.	60
Henan Tianfu Chemical Co.,Ltd.	55
Nanjing ChemLin Chemical Industry Co., Ltd.	60
ATK CHEMICAL COMPANY LIMITED	60
career henan chemical co	58
TargetMol Chemicals Inc.	58
HANGZHOU CLAP TECHNOLOGY CO.,LTD	58
Xi'an MC Biotech, Co., Ltd.	58
RongNa Biotechnology Co.,Ltd	58
Dideu Industries Group Limited	58

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

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2026-01-27	A77 1726 108605-62-5			0.99		RongNa Biotechnology Co.,Ltd
2026-01-24	(E/Z)-Teriflunomide 108605-62-5	US $48.00 / mg		99.76%	10g	TargetMol Chemicals Inc.
2019-07-06	A77 1726 108605-62-5	US $1.00 / KG	1G	99%	100KG	Career Henan Chemical Co

A77 1726
108605-62-5
0.99
RongNa Biotechnology Co.,Ltd

(E/Z)-Teriflunomide
108605-62-5
US $48.00 / mg
99.76%
TargetMol Chemicals Inc.

A77 1726
108605-62-5
US $1.00 / KG
99%
Career Henan Chemical Co

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

2-Cyano-3-hydroxy-N-(4'-trifluoromethylphenyl)-crotone amide(108605-62-5)¹HNMR

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CROTONAMIDE Teriflunomide-d4 2-CYANO-N-P-TOLYL-ACETAMIDE

1of4

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 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 A771726 (Teriflunomide), Active metabolite of leflunomide. Dihydroorotate dehydrogenase inhibitor. (E/Z)-Teriflunomide, 10 mM in DMSO 2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)crotonamide/Leflunomide impurityⅡ 108605-62-5 C12H5F3N2O2D4 Various Metabolites and Impurities Metabolites & Impurities Tyrosine Kinase Inhibitors