General
Preferred name
THALIDOMIDE
Synonyms
N-(2,6-dioxo-3-piperidyl)phthalimide ()
(±)-Thalidomide ()
(+)-THALIDOMIDE ()
(-)-THALIDOMIDE ()
Thalomid ()
Sedoval ()
Kevadon ()
N-Phthaloylglutamimide ()
N-Phthalylglutamic acid imide ()
Neo ()
K-17 ()
E-217 ()
Sedin ()
Nibrol ()
Thalidomide50-35-1 ()
Thalidomide (K17) ()
K17 ()
Pharmion ()
Contergan ()
NSC-527179 ()
Neurosedyn ()
NSC-66847 ()
Myrin ()
Thalidomide ()
Distaval ()
Thaled ()
.alpha.-phthalimidoglutarimide ()
Softenon ()
Pantosediv ()
Celgene ()
Talidex ()
Thalidomide ()
(±)-Thalidomide-d4 ()
P&D ID
PD000977
CAS
50-35-1
841-67-8
2614-06-4
14088-68-7
731-40-8
1012310-87-0
1219177-18-0
Tags
PROTAC
natural product
drug
available
Approved by
PMDA
EMA
FDA
First approval
1998
Drug Status
investigational
approved
withdrawn
Drug indication
Multiple myeloma
Sedative-Hypnotic
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION
Thalidomide is principally an immunomodulatory drug. It inhibits synthesis of TNFα. Mechanistically, thalidomide binds to cereblon, and this complex recruits substrate proteins for degradation by the ubiquitin system. The lymphoid transcription factors Ikaros (IKZF1) and Aiolos (IKZF3) have been identified as substrates for thalidomide-bound cereblon. More recently another transcription factor, PLZF (ZBTB16), has been reported as a potential thalidomide/cereblon substrate . Knockdown of Plfz induces skeletal abnormalities in chicken limbs, so thalidomide-targeted degradation of PLZF would be predicted to exhibit similar teratogenic effects.
SARS-CoV-2 and COVID-19: Thalidomide + low-dose glucocorticoid is being evaluated for efficacy in severe COVID-19 pneumonia (preprint available here https://www.preprints.org/manuscript/202002.0395/v1). An alternative approach is examining the combination of thalidomide + celecoxib (which targets NF-κB to suppress production of inflammatory cytokines; see preprint DOI: 10.13140/RG.2.2.26979.91689). (GtoPdb)
SARS-CoV-2 and COVID-19: Thalidomide + low-dose glucocorticoid is being evaluated for efficacy in severe COVID-19 pneumonia (preprint available here https://www.preprints.org/manuscript/202002.0395/v1). An alternative approach is examining the combination of thalidomide + celecoxib (which targets NF-κB to suppress production of inflammatory cytokines; see preprint DOI: 10.13140/RG.2.2.26979.91689). (GtoPdb)
DESCRIPTION
immunomodulatory drug; binder of cereblon
(Informer Set)
DESCRIPTION
Selective inhibitor of the biosynthesis of tumor necrosis factor a (TNF-alpha); angiogenesis inhibitor
(LOPAC library)
DESCRIPTION
Non-selective NOS inhibitor
(Tocris Bioactive Compound Library)
DESCRIPTION
TNF-α synthesis inhibitor
(Tocriscreen Total)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
1
Organisms
0
Compound Sets
35
AdooQ Bioactive Compound Library
Axon Medchem Screening Library
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
Informer Set
LOPAC library
MedChem Express Bioactive Compound Library
NCATS Inxight Approved Drugs
NIH Approved Oncology Drugs
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Pandemic Response Box
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
Tocris Bioactive Compound Library
Tocriscreen Total
Withdrawn 2.0
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
57
Molecular Weight
258.06
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
1
Rotatable Bonds
1
Ring Count
3
Aromatic Ring Count
1
cLogP
0.09
TPSA
83.55
Fraction CSP3
0.23
Chiral centers
1.0
Largest ring
6.0
QED
0.72
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
CRBN
Protein cereblon
TNF-??
E1/E2/E3 Enzyme
TNFa inhibitor
Bacterial
Ligands for E3 Ligase
Molecular Glues
E3 Ligase ,E3 ligase Ligand,TNF-alpha
Compound status
FDA
Selectivity
TNFalpha
MOA
Unknown molecular target
Inhibitor
DDB1-CRBN modulator
Angiogenesis Inhibitors
TNF-alpha Production Inhibitors
Pathway
Apoptosis
Metabolic Enzyme/Protease
Anti-infection
Autophagy
Primary Target
Ubiquitin E3 Ligases
Member status
member
ATC
L04AX02
Toxicity type
reproductive
Therapeutic Class
Immunosuppressive Agents
Source data
