Teriflunomide - ≥98% , CAS No.163451-81-8

CAS: 163451-81-8 Cat. No.: T413095 Molecular Weight: 270.21 EC Number: 642-273-4 PubChem CID: 54684141

GRADE & PURITY ≥98%

Synonyms

J-010046 | MFCD00910058 | HY-110159 | NCGC00263218-07 | A771726 | A-771726 | A77-1726 | A801897 | SW219377-1 | 2-Butenamide, 2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)- | 2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide | Aubagio | HMS388

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Teriflunomide Teriflunomide (A77 1726, HMR-1726) is the active metabolite of leflunomide, inhibiting pyrimidine de novo synthesis by blocking the enzyme dihydroorotate dehydrogenase, used as an immunomodulatory agent.

Targets

dihydroorotate dehydrogenase

In vitro

Teriflunomide primarily acts as an inhibitor of dihydroorotate dehydrogenase (DHODH), a key mitochondrial enzyme involved in the de novo synthesis of pyrimidines in rapidly proliferating cells. By reducing the activity of high-avidity proliferating T lymphocytes and B lymphocytes, teriflunomide likely attenuates the inflammatory response to autoantigens in MS. Thus, teriflunomide can be considered a cytostatic rather than a cytotoxic drug to leukocytes.

In vivo

Teriflunomide has demonstrated beneficial effects in two independent animal models of demyelinating disease. In the dark agouti rat model of experimental autoimmune encephalitis (EAE), teriflunomide administration results in clinical, histopathological, and electrophysiological evidence of efficacy both as a prophylactic and therapeutic agent. Similarly, in the female Lewis rat model of EAE, teriflunomide administration results in beneficial prophylactic and therapeutic clinical effects, with a delay in disease onset and symptom severity.

Specifications

Synonyms

J-010046 | MFCD00910058 | HY-110159 | NCGC00263218-07 | A771726 | A-771726 | A77-1726 | A801897 | SW219377-1 | 2-Butenamide, 2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)- | 2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide | Aubagio | HMS388

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Teriflunomide (A77 1726, HMR-1726) is the active metabolite of leflunomide, inhibiting pyrimidine de novo synthesis by blocking the enzyme dihydroorotate dehydrogenase, used as an immunomodulatory agent.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(=C(C#N)C(=O)NC1=CC=C(C=C1)C(F)(F)F)O
• IUPAC Name: (Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
• InChIKey: UTNUDOFZCWSZMS-YFHOEESVSA-N
• 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-
• Isomeric SMILES: C/C(=C(\C#N)/C(=O)NC1=CC=C(C=C1)C(F)(F)F)/O
• WGK Germany: 3
• PubChem CID: 54684141
• Molecular Weight: 270.21

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Trifluoromethylbenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Trifluoromethylbenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Trifluoromethylbenzenes
• Alternative Parents: Anilides N-arylamides Vinylogous acids Secondary carboxylic acid amides Nitriles Enols Organopnictogen compounds Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl fluorides
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Trifluoromethylbenzene - Anilide - N-arylamide - Vinylogous acid - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Enol - Carbonitrile - Nitrile - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Carbonyl group - Alkyl halide - Alkyl fluoride - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
• External Descriptors: nitrile - enamide - aromatic amide - enol - (trifluoromethyl)benzenes

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

DHFR Tclin Dihydrofolate reductase (0 Activities)

Discover Target: DHFR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

DHODH Tclin Dihydroorotate dehydrogenase (quinone), mitochondrial (0 Activities)

Discover Target: DHODH

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 27 mg/mL (99.92 mM); Water: Insoluble; Ethanol: Insoluble
• Melt Point(°C): 229 °C
• Molecular Weight: 270.210 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 270.062 Da
• Monoisotopic Mass: 270.062 Da
• Topological Polar Surface Area: 73.100 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 426.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1