Compound Detail

CHEMBL848

LENALIDOMIDE

💊 Approved Drug

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💊 Approved Drug

Nc1cccc2c1CN(C1CCC(=O)NC1=O)C2=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL848
Name	LENALIDOMIDE
Phase	Approved
Structure Type	MOL
InChI Key	GOTYRUGSSMKFNF-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

CC-5013 CDC-501 Lenalidomida Lenalidomide Lenalidomide accord Lenalidomide mylan NSC-747972 Revlimid SYP-1512

145

Targets

615

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

259.3

MW (Da)

0.03

ALogP

HBA

HBD

92.5

PSA (Å²)

0.55

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2005
Availability	Prescription
Chirality	Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product

USAN Stem	-domide
USAN Year	2004

Extended Properties

Molecular Formula	C13H13N3O3
MW	259.26
Aromatic Rings	1
Heavy Atoms	19
NP-Likeness	0.28

Mechanism of Action

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

Indications

Anemia Anemia Immune System Diseases Lymphoma, Mantle-Cell Multiple Myeloma Myelodysplastic Syndromes Amyloidosis Amyloidosis, Familial Epstein-Barr Virus Infections Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Myeloid, Acute Lymphoma Lymphoma, B-Cell, Marginal Zone Lymphoma, B-Cell, Marginal Zone Lymphoma, Follicular Lymphoma, Follicular Lymphoma, Large B-Cell, Diffuse Lymphoma, Non-Hodgkin Melanoma Neoplasm Metastasis

ATC Classification

L04AX04

lenalidomide

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: IMMUNOSUPPRESSANTS

Drug Warnings

Black Box Warning

hematological toxicity

Country: United States

Black Box Warning

vascular toxicity

Country: United States

Black Box Warning

teratogenicity

Country: United States

Black Box Warning

respiratory toxicity

Country: United States

Black Box Warning

musculoskeletal toxicity

Country: United States

Activity Summary

IC50 601 meas. best 7.3

Ki 6 meas. best 6.1

EC50 5 meas. best 7.28

Kd 3 meas. best 6.77

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
MM1.S CHEMBL4296471	IC50	7.3	7.18	50.0	3
Unchecked CHEMBL612545	EC50	7.28	7.28	53.0	1
Cereblon/Ikaros CHEMBL4296103	EC50	7.17	7.17	67.0	1
Zinc finger protein Aiolos CHEMBL4739707	EC50	7.16	7.16	70.0	1
Unchecked CHEMBL612545	IC50	7.09	6.6825	81.0	4
Protein cereblon/Aiolos CHEMBL4296167	EC50	7.06	7.06	87.0	1
Protein cereblon CHEMBL3763008	IC50	7.05	5.5929	89.0	7
Homo sapiens CHEMBL372	IC50	7.0	6.66	100.0	2
PBMC CHEMBL613107	IC50	7.0	7.0	100.0	2
T-cell CHEMBL614309	EC50	6.82	6.82	150.0	1
Protein cereblon/DNA damage-binding protein 1 CHEMBL4630734	Kd	6.77	6.77	170.0	1
Protein cereblon CHEMBL3763008	Kd	6.75	6.75	178.0	1
Unchecked CHEMBL612545	Kd	6.75	6.75	178.0	1
Tumor necrosis factor CHEMBL1825	IC50	6.66	6.66	220.0	1
Protein cereblon/DNA damage-binding protein 1 CHEMBL4630734	IC50	6.54	6.265	286.0	2
NON-PROTEIN TARGET CHEMBL3879801	IC50	6.44	6.44	360.0	1
Interleukin-1 beta CHEMBL1909490	IC50	6.41	6.41	390.0	1
Protein cereblon CHEMBL3763008	Ki	6.1	5.548	800.0	5
LB771-HNC CHEMBL2366099	IC50	5.67	5.67	2150.4	1
L-363 CHEMBL2366267	IC50	5.53	5.53	2922.1	1
JAR CHEMBL614587	IC50	5.53	5.53	2970.0	1
Cereblon isoform 4 CHEMBL3763007	Ki	5.51	5.51	3100.0	1
EOL1 CHEMBL614489	IC50	5.39	5.39	4105.1	1
Bromodomain-containing protein 4 CHEMBL1163125	IC50	5.29	5.29	5190.0	1
BT-549 CHEMBL614072	IC50	5.21	5.21	6218.5	1
SK-NEP-1 CHEMBL1075580	IC50	5.1	5.1	7895.1	1
BV-173 CHEMBL2366145	IC50	5.06	5.06	8675.9	1
HMV-2 cell line CHEMBL614826	IC50	5.0	5.0	10017.2	1
HCC1806 CHEMBL1075457	IC50	4.94	4.94	11446.7	1
Kasumi 1 CHEMBL613988	IC50	4.94	4.94	11571.0	1
SK-MEL-28 CHEMBL614919	IC50	4.92	4.92	11976.4	1
RPMI-8226 CHEMBL614882	IC50	4.9	4.9	12624.1	1
T47D CHEMBL614361	IC50	4.88	4.88	13209.9	1
HOP-62 CHEMBL614643	IC50	4.87	4.87	13480.0	1
A2058 CHEMBL613503	IC50	4.86	4.86	13819.9	1
SW-620 CHEMBL612262	IC50	4.85	4.85	14247.3	1
HAL-01 CHEMBL2366142	IC50	4.84	4.84	14579.6	1
LCLC-103H cell line CHEMBL614066	IC50	4.84	4.84	14489.2	1
PANC-08-13 CHEMBL1075558	IC50	4.83	4.83	14910.9	1
COLO-684 CHEMBL2366176	IC50	4.81	4.81	15397.9	1
DEL CHEMBL2366186	IC50	4.81	4.81	15499.0	1
K5 CHEMBL2366152	IC50	4.79	4.79	16148.6	1
ACN CHEMBL2366195	IC50	4.78	4.78	16529.7	1
SK-MEL-24 CHEMBL2366314	IC50	4.78	4.78	16465.2	1
H9 CHEMBL614806	IC50	4.78	4.78	16626.0	1
EM-2 CHEMBL2366281	IC50	4.77	4.77	17143.0	1
HSC-4 CHEMBL1075469	IC50	4.75	4.75	17660.1	1
TE-1 CHEMBL2366092	IC50	4.75	4.75	17996.8	1
IGROV-1 CHEMBL613984	IC50	4.75	4.75	17783.0	1
LN-405 CHEMBL1075491	IC50	4.7	4.7	19907.6	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	138.7	ml/min	Homo sapiens
F	500.0	%	Homo sapiens
Fu	1.0	-	Homo sapiens
T1/2	19.3	hr	Homo sapiens
T1/2	2.067	hr	Homo sapiens
T1/2	4.733	hr	Homo sapiens
T1/2	6.0	hr	Mus musculus
T1/2	6.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
MM1.S	IC50	=	50.0	nM	7.3	Antiproliferative activity against human MM1S cells measured after 168 hrs by Ce...	31125896
Unchecked	EC50	=	53.0	nM	7.28	Induction of CRL4/CRBN ubiquitin ligase-mediated aiolos degradation in human DF1...	28358507
Cereblon/Ikaros	EC50	=	67.0	nM	7.17	Induction of cereblon-mediated ikaros degradation in human DF15 cells expressing...	28425720
Zinc finger protein Aiolos	EC50	=	70.0	nM	7.16	Induction of ePL tagged Aiolos degradation in human DF15 cells incubated for 4 h...	37991844
MM1.S	IC50	=	70.17	nM	7.15	Antiproliferative activity against human MM1.S cells assessed as cell viability ...	35635954
MM1.S	IC50	=	81.0	nM	7.09	Antiproliferative activity against human MM1.S cells assessed as reduction in ce...	33328101
Unchecked	IC50	=	81.0	nM	7.09	Immunomodulatory activity in human MM cells	34974338
Protein cereblon/Aiolos	EC50	=	87.0	nM	7.06	Induction of cereblon-mediated aiolos degradation in human DF15 cells expressing...	28425720
Protein cereblon	IC50	=	88.99	nM	7.05	Inhibition of CRBN (unknown origin) measured after 60 mins incubation by BMG rea...	38321747
Homo sapiens	IC50	=	100.0	nM	7.0	Inhibition of lipopolysaccharide stimulated TNF-alpha release in human whole blo...	10386948
PBMC	IC50	=	100.0	nM	7.0	Inhibition of TNF-alpha production in LPS-stimulated human PBMC preincubated for...	23168019
PBMC	IC50	=	100.0	nM	7.0	Antiinflammatory activity in human PBMC cells assessed as reduction in LPS-induc...	31125896
Unchecked	IC50	=	100.0	nM	7.0	Inhibition of TNF-alpha release in LPS stimulated human PBMC	33906050
T-cell	EC50	=	150.0	nM	6.82	Inhibition of IL-2 production in human T cells measured after 2 to 3 days by ELI...	23168019
Protein cereblon/DNA damage-binding protein 1	Kd	=	170.0	nM	6.77	Binding affinity to recombinant human CRBN/DDB1 assessed as dissociation constan...	36749666
Protein cereblon	Kd	=	178.0	nM	6.75	Binding affinity to CRBN (unknown origin) assessed as dissociation constant by T...	37984298
Unchecked	Kd	=	178.0	nM	6.75	Binding affinity to human CRBN (1 to 442 residues)/N-terminal 6His-tagged human ...	31117518
Unchecked	IC50	=	190.0	nM	6.72	cytomteric bead array (CBA) assay: The Fix buffer I was warmed up to 37° C. in a...	-
Tumor necrosis factor	IC50	=	220.0	nM	6.66	cytomteric bead array (CBA) assay: The Fix buffer I was warmed up to 37° C. in a...	-
Protein cereblon/DNA damage-binding protein 1	IC50	=	286.0	nM	6.54	Displacement of Cy5-O-Len probe from 6XHis-tagged CRBN/DDB1 (unknown origin) inc...	34042448

Literature References

PubMed	DOI	Target Context	# Activities
17576924	10.1073/pnas.0610477104	Molecular identity unknown	65
33210536	10.1021/acs.jnatprod.0c00350	Unchecked	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
-	10.1039/C4MD00070F	Jurkat	8
34795877	10.1021/acsmedchemlett.1c00475	ADMET	8
33773263	10.1016/j.ejmech.2021.113353	Unchecked	8
17576924	10.1073/pnas.0610477104	Unchecked	6
37902300	10.1021/acs.jmedchem.3c00851	No relevant target	6
33773263	10.1016/j.ejmech.2021.113353	Transcription factor p65	4
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M1	4
28757066	10.1016/j.bmcl.2017.07.046	EC9706	4
28358507	10.1021/acs.jmedchem.6b01911	Unchecked	4
37468498	10.1038/s41467-023-40064-9	Prostaglandin G/H synthase 1	4
37468498	10.1038/s41467-023-40064-9	Thromboxane A2 receptor	4
33328101	10.1016/j.ejmech.2020.112912	ADMET	4
36749666	10.1021/acs.jmedchem.2c01941	No relevant target	4
17576924	10.1073/pnas.0610477104	NON-PROTEIN TARGET	4
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	4
33773263	10.1016/j.ejmech.2021.113353	Signal transducer and activator of transcription 3	4
28425720	10.1021/acs.jmedchem.6b01921	Protein cereblon/Aiolos	3

Data from ChEMBL 36 via Core Engine