Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL973

TERIFLUNOMIDE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
C/C(O)=C(\C#N)C(=O)Nc1ccc(C(F)(F)F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL973
Name TERIFLUNOMIDE
Phase Approved
Structure Type MOL
InChI Key UTNUDOFZCWSZMS-YFHOEESVSA-N
Therapeutic ✓ Yes

Known Names

A77 1726 Aubagio HMR-1726 HMR1726 Leflunomide related compound b Leflunomide related compound b rs Teriflunomida Teriflunomide Teriflunomide accord Teriflunomide mylan
15
Targets
70
Activities
3
Assay Types
2
PK Parameters
20
Publications
10
Known Names
7
Indications
1
Mechanisms

Molecular Properties

270.2
MW (Da)
3.00
ALogP
3
HBA
2
HBD
73.1
PSA (Ų)
0.49
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2012
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning First in Class
USAN Year 2011

Extended Properties

Molecular Formula C12H9F3N2O2
MW 270.21
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -1.35

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dihydroorotate dehydrogenase inhibitor INHIBITOR Dihydroorotate dehydrogenase (quinone), mitochondrial ✓ ✓

Indications

Multiple Sclerosis Multiple Sclerosis, Relapsing-Remitting Multiple Sclerosis, Chronic Progressive Purpura, Thrombocytopenic, Idiopathic Celiac Disease Kidney Diseases Paraparesis, Tropical Spastic

ATC Classification

L04AK02
teriflunomide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 63 meas. best 8.05
Ki 5 meas. best 7.52
EC50 2 meas. best 5.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL2383
 IC50 8.05 7.7771 9.0 7
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 Ki 7.52 6.8633 30.0 3
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL2991
 IC50 7.16 6.9375 69.0 4
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 IC50 6.89 6.4075 130.0 20
Unchecked
CHEMBL612545
 IC50 6.7 6.01 200.0 8
Dihydrofolate reductase
CHEMBL202
 IC50 6.41 6.41 388.0 1
Dihydroorotate dehydrogenase
CHEMBL3486
 IC50 5.41 5.175 3900.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.39 4.855 4070.0 2
ORAI1/STIM1
CHEMBL3832644
 IC50 5.37 5.37 4300.0 1
Splenocyte
CHEMBL612422
 IC50 5.17 5.17 6700.0 1
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL1966
 EC50 5.05 5.05 8900.0 2
MDA-MB-231
CHEMBL400
 IC50 4.85 4.85 14000.0 1
Dihydroorotate dehydrogenase
CHEMBL3486
 Ki 4.66 4.645 22000.0 2
Jurkat
CHEMBL397
 IC50 4.57 4.3775 26650.0 4
Mus musculus
CHEMBL375
 IC50 4.38 4.38 41300.0 1
PBMC
CHEMBL613107
 IC50 4.34 4.3 46000.0 2
Dihydroorotate dehydrogenase (quinone), mitochondrial
CHEMBL4523950
 IC50 4.3 4.3 50000.0 2
ADMET
CHEMBL612558
 IC50 4.29 4.1567 50900.0 3

Pharmacokinetic Data

Parameter Value Units Species
T1/2 14.1 hr Rattus norvegicus
T1/2 336.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 9.0 nM 8.05 Inhibitory activity against rat dihydroorotate dehydrogenase 16143532
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 13.0 nM 7.89 Inhibitory concentration tested against enzyme dihydroorotate dehydrogenase in r... 8917650
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 17.0 nM 7.77 Inhibition of C-terminal His6-tagged rat DHODH expressed in Escherichia coli BL2... 32248693
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 18.0 nM 7.75 Inhibition of rat DHODH (amino acid residues 30 to 396) expressed in Escherichia... 24801997
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 20.0 nM 7.7 Inhibition of DHODH in Wistar rat liver homogenates by DCIP reduction assay 21109332
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 20.0 nM 7.7 Inhibition of dihydroorotate dehydrogenase in Wistar rat liver mitochondrial/mic... 22245049
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 26.0 nM 7.58 Inhibition of rat dihydroorotate dehydrogenase 22078215
Dihydroorotate dehydrogenase (quinone), mitochondrial Ki = 30.0 nM 7.52 Inhibition of human recombinant DHODH 17228860
Dihydroorotate dehydrogenase (quinone), mitochondrial Ki = 32.0 nM 7.5 Inhibition of ubiquinone binding site of human dihydroorotate dehydrogenase 19351152
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 69.0 nM 7.16 Inhibitory concentration tested on enzyme dihydroorotate dehydrogenase in mouse 8917650
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 110.0 nM 6.96 Inhibition of C-terminal His6-tagged mouse DHODH expressed in Escherichia coli B... 32248693
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 130.0 nM 6.89 Inhibition of human DHODH expressed in Escherichia coli BL21(DE3) using L-dihydr... 22984987
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 137.0 nM 6.86 Inhibition of N-terminal His10-tagged human DHODH (Met30 to Arg396) expressed in... 24073986
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 150.0 nM 6.82 Inhibition of mouse DHODH (amino acid residues 30 to 396) expressed in Escherich... 24801997
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 156.0 nM 6.81 Inhibitory activity against mouse dihydroorotate dehydrogenase 16143532
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 163.0 nM 6.79 Inhibition of human DHODH using dihydroorotate substrate by DCIP assay 25580811
Unchecked IC50 = 200.0 nM 6.7 Inhibition of C-terminal His6-tagged dog DHODH expressed in Escherichia coli BL2... 32248693
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 210.0 nM 6.68 Inhibition of C-terminal His6-tagged human DHODH (amino acid residues 30 to 396)... 24801997
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 227.0 nM 6.64 Inhibition of human recombinant DHODH expressed in Escherichia coli BL21 (DE3) u... 34957834
Dihydroorotate dehydrogenase (quinone), mitochondrial IC50 = 261.0 nM 6.58 Inhibition of ubiquinone binding site of human dihydroorotate dehydrogenase 19351152

Literature References

PubMed DOI Target Context # Activities
24801997 10.1021/jm500481t Unchecked 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
24801997 10.1021/jm500481t Dihydroorotate dehydrogenase (quinone), mitochondrial 4
29939742 10.1021/acs.jmedchem.8b00373 No relevant target 3
36115209 10.1016/j.ejmech.2022.114737 Dihydroorotate dehydrogenase (quinone), mitochondrial 3
32248693 10.1021/acs.jmedchem.0c00311 Dihydroorotate dehydrogenase (quinone), mitochondrial 3
29939742 10.1021/acs.jmedchem.8b00373 Jurkat 3
17228860 10.1021/jm060687j Dihydroorotate dehydrogenase (quinone), mitochondrial 3
35640328 10.1016/j.ejmech.2022.114489 Dihydroorotate dehydrogenase (quinone), mitochondrial 3
16143532 10.1016/j.bmcl.2005.07.053 Dihydroorotate dehydrogenase (quinone), mitochondrial 3
30776695 10.1016/j.ejmech.2019.02.018 Dihydroorotate dehydrogenase (quinone), mitochondrial 3
28235702 10.1016/j.ejmech.2017.02.017 Jurkat 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
9207942 10.1021/jm970039n ADMET 3
26079043 10.1021/acs.jmedchem.5b00606 Measles morbillivirus 2
8917650 10.1021/jm9604437 Dihydroorotate dehydrogenase (quinone), mitochondrial 2
22984987 10.1021/jm300630p NON-PROTEIN TARGET 2
19351152 10.1021/jm800963t Dihydroorotate dehydrogenase (quinone), mitochondrial 2
19351152 10.1021/jm800963t Dihydroorotate dehydrogenase 2
22078215 10.1016/j.bmcl.2011.10.052 Dihydroorotate dehydrogenase (quinone), mitochondrial 2

Data from ChEMBL 36 via Core Engine