General
Preferred name
THALIDOMIDE
Synonyms
N-(2,6-dioxo-3-piperidyl)phthalimide ()
(±)-Thalidomide ()
(+)-THALIDOMIDE ()
(-)-THALIDOMIDE ()
Thalomid ()
Sedoval ()
Thalidomide50-35-1 ()
K17 ()
Thalidomide (K17) ()
1a(thal) ()
ThalidomideKevadonThalomidN-PhthaloylglutamimideN-Phthalylglutamic acid imideNeoK-17E-217SedinNibrol ()
Contergan ()
Kevadon ()
NSC-66847 ()
Neurosedyn ()
Talidex ()
.alpha.-phthalimidoglutarimide ()
Myrin ()
Thalidomide lipomed ()
NSC-527179 ()
Thalidomide bms (previously thalidomide celgene) ()
Pharmion ()
K-17 ()
Talidomida ()
Thaled ()
Celgene ()
N-Phthalylglutamic acid imide ()
Softenon ()
Pantosediv ()
Distaval ()
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
available
molecular glue
PROTAC
drug
Approved by
EMA
PMDA
FDA
First approval
1998
1956
Drug indication
Immune System disease
Multiple myeloma
Drug Status
approved
withdrawn
investigational
Max Phase
4.0
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
Thalidomide inhibits cereblon (CRBN), a part of the cullin-4 E3 ubiquitin ligase complex CUL4-RBX1-DDB1, with a Kd of ¡«250 nM, and has immunomodulatory, anti-inflammatory and anti-angiogenic cancer properties. Thalidomide can work as molecular glue to potentiate substrate.
DESCRIPTION
immunomodulatory drug; binder of cereblon
(Informer Set)
DESCRIPTION
Non-selective NOS inhibitor
(Tocris Bioactive Compound Library)
DESCRIPTION
Selective inhibitor of the biosynthesis of tumor necrosis factor a (TNF-alpha); angiogenesis inhibitor
(LOPAC library)
DESCRIPTION
TNF-α synthesis inhibitor
(Tocriscreen Total)
DESCRIPTION
Thalidomide is an immunomodulatory compound with diverse biological activities, including anticancer, anti-inflammatory, and teratogenic properties. Thalidomide is indicated for the acute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL). Also for use as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence.
(Enamine Bioactive Compounds)
DESCRIPTION
Thalidomide (Thalomid) is a synthetic derivative of glutamic acid (alpha-phthalimido-glutarimide) with teratogenic, immunomodulatory, anti-inflammatory and anti-angiogenic properties.
(TargetMol Bioactive Compound Library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
1
Organisms
0
Compound Sets
38
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
CZ-OPENSCREEN Bioactive Library
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Enamine Bioactive Compounds
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
Informer Set
LOPAC library
MedChem Express Bioactive Compound Library
MolGlueDB
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
60
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
E1/E2/E3 Enzyme
TNFa inhibitor
Ligands for E3 Ligase
Molecular Glues
E3 Ligase ,E3 ligase Ligand,TNF-alpha
Ligand for E3 Ligase
TNF-α
Compound status
FDA
Selectivity
TNFalpha
MOA
Unknown molecular target
Inhibitor
DDB1-CRBN modulator
Angiogenesis Inhibitors
TNF-alpha Production Inhibitors
Pathway
Apoptosis
Autophagy
Metabolic Enzyme/Protease
Primary Target
Ubiquitin E3 Ligases
Member status
member
ATC
L04AX02
Toxicity type
reproductive
Therapeutic Class
Immunosuppressive Agents
Source data
