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Compound Detail

CHEMBL468

THALIDOMIDE
💊 Approved Drug
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💊 Approved Drug
O=C1CCC(N2C(=O)c3ccccc3C2=O)C(=O)N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL468
Name THALIDOMIDE
Phase Approved
Structure Type MOL
InChI Key UEJJHQNACJXSKW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

.alpha.-phthalimidoglutarimide Celgene Contergan Distaval K-17 Kevadon Myrin N-phthalylglutamic acid imide Neurosedyn NSC-527179 NSC-66847 Pantosediv +9 more
8
Targets
37
Activities
4
Assay Types
9
PK Parameters
20
Publications
21
Known Names
20
Indications
1
Mechanisms

Molecular Properties

258.2
MW (Da)
0.09
ALogP
4
HBA
1
HBD
83.5
PSA (Ų)
0.72
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1956
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn Natural Product
USAN Stem -domide
USAN Year 1961

Extended Properties

Molecular Formula C13H10N2O4
MW 258.23
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness -0.24

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
CRL4(CRBN) E3 ubiquitin ligase inhibitor INHIBITOR CRL4(CRBN) E3 ubiquitin ligase ✓ ✓

Indications

Immune System Diseases Multiple Myeloma Amyloidosis, Familial beta-Thalassemia Carcinoma, Hepatocellular Carcinoma, Ovarian Epithelial Colitis, Ulcerative Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Cough Crohn Disease Fallopian Tube Neoplasms Granuloma, Lethal Midline Hypoalbuminemia Idiopathic Pulmonary Fibrosis Kidney Neoplasms Kidney Neoplasms Lung Neoplasms

ATC Classification

L04AX02
thalidomide
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Withdrawn
teratogenicity
teratogenic effects
Country: Finland   Year: 1963
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
vascular toxicity
Country: United States

Activity Summary

IC50 20 meas. best 6.57
Ki 12 meas. best 5.75
Kd 3 meas. best 6.6
EC50 2 meas. best 7.44

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protein cereblon/DNA damage-binding protein 1
CHEMBL4630734
 EC50 7.44 7.44 36.0 1
Protein cereblon
CHEMBL3763008
 Kd 6.6 6.6 250.0 2
Unchecked
CHEMBL612545
 Kd 6.6 6.6 250.0 1
Protein cereblon/DNA damage-binding protein 1
CHEMBL4630734
 IC50 6.57 6.3 268.0 4
Zinc finger protein Aiolos
CHEMBL4739707
 EC50 6.48 6.48 330.0 1
Prostaglandin G/H synthase 1
CHEMBL2949
 IC50 6.43 6.43 370.0 1
Prostaglandin G/H synthase 2
CHEMBL4102
 IC50 6.3 6.3 500.0 1
Protein cereblon
CHEMBL3763008
 IC50 5.83 5.22 1490.0 5
Protein cereblon
CHEMBL3763008
 Ki 5.75 5.2225 1800.0 8
Unchecked
CHEMBL612545
 IC50 5.69 5.21 2040.0 2
Cereblon isoform 4
CHEMBL3763007
 Ki 5.36 5.2467 4400.0 3
Cereblon isoform 4
CHEMBL3763007
 IC50 5.11 5.04 7800.0 2
Unchecked
CHEMBL612545
 Ki 4.79 4.79 16100.0 1
PBMC
CHEMBL613107
 IC50 4.11 4.11 77000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.4 mL.min-1.kg-1 Homo sapiens
F 300.0 % Homo sapiens
Fu 0.4 - Homo sapiens
Fu 0.34 - Homo sapiens
MRT 4.3 hr Homo sapiens
T1/2 4.7 hr Homo sapiens
T1/2 5.5 hr Homo sapiens
T1/2 3.1 hr Homo sapiens
T1/2 0.3667 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protein cereblon/DNA damage-binding protein 1 EC50 = 36.0 nM 7.44 Displacement of BODIPY FL thalidomide from 6His-tagged CRBN/DDB1 (unknown origin... 35978691
Protein cereblon Kd = 250.0 nM 6.6 Binding affinity to CRBN (unknown origin) assessed as dissociation constant 37210838
Protein cereblon Kd = 250.0 nM 6.6 Binding affinity to CRBN (unknown origin) assessed as dissociation constant by T... 37984298
Unchecked Kd = 250.0 nM 6.6 Binding affinity to human CRBN (1 to 442 residues)/N-terminal 6His-tagged human ... 31117518
Protein cereblon/DNA damage-binding protein 1 IC50 = 268.0 nM 6.57 CRBN-DDB1 ligand-displacement AlphaScreen Assay: A thalidomide competition Alpha... -
Protein cereblon/DNA damage-binding protein 1 IC50 = 301.0 nM 6.52 CRBN-DDB1 ligand-displacement AlphaScreen Assay: A thalidomide competition Alpha... -
Zinc finger protein Aiolos EC50 = 330.0 nM 6.48 Induction of ePL tagged Aiolos degradation in human DF15 cells incubated for 4 h... 37991844
Prostaglandin G/H synthase 1 IC50 = 370.0 nM 6.43 Inhibitory activity (RA1) against Prostaglandin G/H synthase 1 was calculated re... 11909713
Prostaglandin G/H synthase 2 IC50 = 500.0 nM 6.3 Inhibitory activity (RA2) against Prostaglandin G/H synthase 2 was calculated re... 11909713
Protein cereblon/DNA damage-binding protein 1 IC50 = 560.0 nM 6.25 Displacement of Cy5-labeled tracer CC0782985 from 6His-tagged CRBN (1 to 442 res... 37991844
Protein cereblon/DNA damage-binding protein 1 IC50 = 1380.0 nM 5.86 Displacement of Cy5-O-Len probe from 6XHis-tagged CRBN/DDB1 (unknown origin) inc... 34042448
Protein cereblon IC50 = 1490.0 nM 5.83 Displacement of fluorescent tracer from NanoLuc-tagged CRBN (unknown origin) by ... 36970148
Protein cereblon Ki = 1800.0 nM 5.75 Binding affinity to CRBN (unknown origin) assessed as inhibition constant 37683104
Protein cereblon Ki = 1800.0 nM 5.75 Binding affinity to GST-tagged wild-type human CRBN incubated for 3 hrs by TR-FR... 39132814
Unchecked IC50 = 2040.0 nM 5.69 Inhibition of IL-1-alpha-induced NF-kappaB activation in HeLa cells assessed as ... 17845850
Protein cereblon IC50 = 2700.0 nM 5.57 Inhibition of biotinylated thalidomide binding to CRBN (40 to 442 residues) (unk... 38829718
Protein cereblon IC50 = 2900.0 nM 5.54 Binding affinity to GST-tagged wild type human CRBN incubated for 3 hrs by TR-FR... 37647546
Protein cereblon Ki = 4400.0 nM 5.36 Binding affinity to CRBN (unknown origin) assessed as inhibition constant by FRE... 36821822
Cereblon isoform 4 Ki = 4400.0 nM 5.36 Inhibition of MANT-uracil binding to wild type Magnetospirillum gryphiswaldense ... 26730808
Cereblon isoform 4 Ki = 4400.0 nM 5.36 Inhibition of MANT-uracil binding to wild-type Magnetospirillum gryphiswaldense ... 31251063

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 227
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
18951804 10.1016/j.bmc.2008.09.071 Ehrlich 10
20598893 10.1016/j.bmc.2010.06.002 Mus musculus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18723357 10.1016/j.bmc.2008.08.004 RAW264.7 8
34795877 10.1021/acsmedchemlett.1c00475 ADMET 7
22356737 10.1016/j.bmc.2012.01.034 Unchecked 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
18951804 10.1016/j.bmc.2008.09.071 Mus musculus 5
- 10.1039/C4MD00070F Jurkat 4
20034801 10.1016/j.bmc.2009.12.001 Jurkat 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
33606537 10.1021/acs.jmedchem.0c02234 Unchecked 4
19297157 10.1016/j.bmcl.2009.02.108 HUVEC 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
8759624 10.1021/jm960284r Tumor necrosis factor 4
26730808 10.1021/acs.jmedchem.5b01735 Cereblon isoform 4 4

Data from ChEMBL 36 via Core Engine