CHEBI:6402 - leflunomide

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ChEBI Name leflunomide
ChEBI ID CHEBI:6402
Definition A monocarboxylic acid amide obtained by formal condensation of the carboxy group of 5-methyl-1,2-oxazole-4-carboxylic acid with the anilino group of 4-(trifluoromethyl)aniline. The prodrug of teriflunomide.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000100090361
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Leflunomide, sold under the brand name Arava among others, is an immunosuppressive disease-modifying antirheumatic drug (DMARD), used in active moderate-to-severe rheumatoid arthritis and psoriatic arthritis. It is a pyrimidine synthesis inhibitor that works by inhibiting dihydroorotate dehydrogenase.
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Formula C12H9F3N2O2
Net Charge 0
Average Mass 270.20730
Monoisotopic Mass 270.06161
InChI InChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18)
InChIKey VHOGYURTWQBHIL-UHFFFAOYSA-N
SMILES Cc1oncc1C(=O)Nc1ccc(cc1)C(F)(F)F
Roles Classification
Biological Role(s): tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor
An EC 1.3.98.* (oxidoreductase acting on CH-CH group of donors, with other, known, acceptors) inhibitor that interferes with the action of dihydroorotate oxidase (fumarate), EC 1.3.98.1 (formerly EC 1.3.3.1).
hepatotoxic agent
A role played by a chemical compound exhibiting itself through the ability to induce damage to the liver in animals.
pyrimidine synthesis inhibitor
A pathway inhibitor that inhibits the synthesis of pyrimidine.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor
Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiparasitic agent
A substance used to treat or prevent parasitic infections.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
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ChEBI Ontology
Outgoing leflunomide (CHEBI:6402) has role antineoplastic agent (CHEBI:35610)
leflunomide (CHEBI:6402) has role antiparasitic agent (CHEBI:35442)
leflunomide (CHEBI:6402) has role EC 1.3.98.1 [dihydroorotate oxidase (fumarate)] inhibitor (CHEBI:68542)
leflunomide (CHEBI:6402) has role EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (CHEBI:37153)
leflunomide (CHEBI:6402) has role hepatotoxic agent (CHEBI:50908)
leflunomide (CHEBI:6402) has role immunosuppressive agent (CHEBI:35705)
leflunomide (CHEBI:6402) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
leflunomide (CHEBI:6402) has role prodrug (CHEBI:50266)
leflunomide (CHEBI:6402) has role pyrimidine synthesis inhibitor (CHEBI:68543)
leflunomide (CHEBI:6402) has role tyrosine kinase inhibitor (CHEBI:38637)
leflunomide (CHEBI:6402) is a (trifluoromethyl)benzenes (CHEBI:83565)
leflunomide (CHEBI:6402) is a isoxazoles (CHEBI:55373)
leflunomide (CHEBI:6402) is a monocarboxylic acid amide (CHEBI:29347)
IUPAC Name
5-methyl-N-[4-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide
INNs Sources
leflunomida WHO MedNet
leflunomide WHO MedNet
léflunomide WHO MedNet
leflunomidum WHO MedNet
Synonyms Sources
5-Methyl-N-(4-(trifluoromethyl)phenyl)-4-isoxazolecarboxamide ChemIDplus
5-Methylisoxazole-4-carboxylic acid (4-trifluoromethyl)anilide ChEBI
alpha,alpha,alpha-Trifluoro-5-methyl-4-isoxazolecarboxy-p-toluidide ChemIDplus
Leflunomide KEGG COMPOUND
Brand Name Source
Arava KEGG DRUG
Manual Xrefs Databases
1552 DrugCentral
C07905 KEGG COMPOUND
D00749 KEGG DRUG
DB01097 DrugBank
DE2854439 Patent
HMDB0015229 HMDB
Leflunomide Wikipedia
LSM-3771 LINCS
US4284786 Patent
View more database links
Registry Numbers Types Sources
4323174 Reaxys Registry Number Reaxys
75706-12-6 CAS Registry Number KEGG COMPOUND
75706-12-6 CAS Registry Number ChemIDplus
Citations
Last Modified
22 February 2017