A26

(2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide

Created:	1999-10-01
Last modified:	2021-03-01

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2 entries where A26 is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	28
Chiral Atom Count	0
Bond Count	28
Aromatic Bond Count	6

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Chemical Component Summary
Name	(2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
Synonyms	ANTIPROLIFERATIVE AGENT A771726
Systematic Name (OpenEye OEToolkits)	(Z)-2-cyano-3-oxidanyl-N-[4-(trifluoromethyl)phenyl]but-2-enamide
Formula	C₁₂ H₉ F₃ N₂ O₂
Molecular Weight	270.207
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O=C(Nc1ccc(cc1)C(F)(F)F)C(/C#N)=C(\O)C
SMILES	CACTVS	3.370	CC(O)=C(C#N)C(=O)Nc1ccc(cc1)C(F)(F)F
SMILES	OpenEye OEToolkits	1.7.6	CC(=C(C#N)C(=O)Nc1ccc(cc1)C(F)(F)F)O
Canonical SMILES	CACTVS	3.370	CC(/O)=C(C#N)/C(=O)Nc1ccc(cc1)C(F)(F)F
Canonical SMILES	OpenEye OEToolkits	1.7.6	C/C(=C(\C#N)/C(=O)Nc1ccc(cc1)C(F)(F)F)/O
InChI	InChI	1.03	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	InChI	1.03	UTNUDOFZCWSZMS-YFHOEESVSA-N

Drug Info: DrugBank

DrugBank ID	DB08880
Name	Teriflunomide
Groups	approved
Description	Teriflunomide is the active metabolite of leflunomide, and it acts as an immunomodulatory agent by inhibiting pyrimidine synthesis. It is marketed under the name Aubagio® and is indicated for the treatment of multiple sclerosis, specifically relapsing forms. The FDA label states an important warning about the risk of hepatoxicity and teratogenicity for patients using teriflunomide.
Synonyms	Teriflunomide Tériflunomide Teriflunomida (Z)-2-cyano-alpha,alpha,alpha-trifluoro-3-hydroxy-p-crotonotoluidide Teriflunomidum
Brand Names	Sandoz Teriflunomide Teriflunomide Jamp Teriflunomide M-teriflunomide Teriflunomide Mylan Teriflunomide Accord Teva-teriflunomide Aubagio Auro-teriflunomide Ach-teriflunomide Nat-teriflunomide Apo-teriflunomide PMS-teriflunomide Mar-teriflunomide
Indication	Used in the treatment of relapsing forms of multiple sclerosis (MS).
Categories	Acids, Acyclic Amines Analgesics Analgesics, Non-Narcotic Aniline Compounds Anti-Inflammatory Agents Antineoplastic and Immunomodulating Agents Antirheumatic Agents BCRP/ABCG2 Inhibitors BCRP/ABCG2 Substrates Benzene Derivatives Butyrates Cytochrome P-450 CYP1A2 Inducers Cytochrome P-450 CYP1A2 Inducers (strength unknown) Cytochrome P-450 CYP1A2 Inducers (weak) Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (moderate) Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Dihydroorotate Dehydrogenase Inhibitors Fatty Acids Fatty Acids, Volatile Hepatotoxic Agents Hydroxy Acids Immunologic Factors Immunomodulatory Agents Immunosuppressive Agents Lipids OAT3/SLC22A8 Inhibitors OATP1B1/SLCO1B1 Inhibitors Peripheral Nervous System Agents Pyrimidine Synthesis Inhibitor Selective Immunosuppressants Sensory System Agents
ATC-Code	L04AA31
CAS number	163451-81-8

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Dihydroorotate dehydrogenase (quinone), mitochondrial	MAWRHLKKRAQDAVIILGGGGLLFASYLMATGDERFYAEHLMPTLQGLLD...	unknown	inhibitor
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	inducer
ATP-binding cassette sub-family G member 2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682