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Compound Detail

CHEMBL2107333

DIMETHYL FUMARATE
💊 Approved Drug
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💊 Approved Drug
COC(=O)/C=C/C(=O)OC

Basic Information

ChEMBL ID CHEMBL2107333
Name DIMETHYL FUMARATE
Phase Approved
Structure Type MOL
InChI Key LDCRTTXIJACKKU-ONEGZZNKSA-N
Therapeutic ✓ Yes

Known Names

AZL 0 211089 AZL O 211089 AZL-0211089 AZL-O-211089 BG 00012 BG 12 BG-00012 BG-12 BG00012 Dimethyl fumar Dimethyl fumarate Dimethyl fumarate accord +15 more
5
Targets
12
Activities
3
Assay Types
1
PK Parameters
20
Publications
27
Known Names
15
Indications
1
Mechanisms

Molecular Properties

144.1
MW (Da)
-0.11
ALogP
4
HBA
0
HBD
52.6
PSA (Ų)
0.40
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product First in Class
USAN Year 2005

Extended Properties

Molecular Formula C6H8O4
MW 144.13
Aromatic Rings 0
Heavy Atoms 10
NP-Likeness 0.49

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Kelch-like ECH-associated protein 1 inhibitor INHIBITOR Kelch-like ECH-associated protein 1

Indications

Immune System Diseases Multiple Sclerosis Multiple Sclerosis, Relapsing-Remitting Psoriasis Multiple Sclerosis, Chronic Progressive Multiple Sclerosis, Chronic Progressive Severe Acute Respiratory Syndrome Arthritis, Psoriatic Arthritis, Rheumatoid Cerebral Hemorrhage Ischemic Stroke Lymphoma, T-Cell, Cutaneous Sleep Apnea, Obstructive Gliosarcoma Leukemia, Lymphocytic, Chronic, B-Cell

ATC Classification

L04AX07
dimethyl fumarate
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Activity Summary

EC50 5 meas. best 5.29
IC50 4 meas. best 6.89
Ki 3 meas. best 4.67

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hydroxycarboxylic acid receptor 2
CHEMBL3785
IC50 6.89 6.89 130.0 1
Nuclear factor erythroid 2-related factor 2
CHEMBL1075094
EC50 5.29 5.195 5114.0 2
Keap1/Nrf2
CHEMBL3038498
EC50 5.29 5.29 5110.0 1
THP-1
CHEMBL614245
IC50 4.97 4.97 10600.0 1
Unchecked
CHEMBL612545
Ki 4.67 4.665 21300.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.2 hr -

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
26111355 10.1021/acs.jmedchem.5b00170 Nuclear factor erythroid 2-related factor 2 7
28410442 10.1021/acs.jmedchem.6b01624 NACHT, LRR and PYD domains-containing protein 3 7
28236590 10.1016/j.bmcl.2017.02.022 Unchecked 6
38142510 10.1016/j.ejmech.2023.116080 Mus musculus 6
30321804 10.1016/j.ejmech.2018.10.010 Unchecked 6
38116420 10.1021/acsmedchemlett.3c00336 Nuclear factor erythroid 2-related factor 2 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
321785 10.1021/jm00214a038 Candida albicans 4
321785 10.1021/jm00214a038 Aspergillus niger 4
321785 10.1021/jm00214a038 Mucor mucedo 4
321785 10.1021/jm00214a038 Trichophyton mentagrophytes 4
23647822 10.1016/j.bmc.2013.04.019 Nuclear factor erythroid 2-related factor 2 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
33894507 10.1016/j.bmc.2021.116141 Unchecked 3
37468498 10.1038/s41467-023-40064-9 Histamine H1 receptor 3
28236590 10.1016/j.bmcl.2017.02.022 No relevant target 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
34985276 10.1021/acs.jmedchem.1c01255 HEK-293T 2
32898762 10.1016/j.ejmech.2020.112740 Glyceraldehyde-3-phosphate dehydrogenase 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2

Data from ChEMBL 36 via Core Engine