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Compound Detail

CHEMBL1023

BEXAROTENE
💊 Approved Drug
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💊 Approved Drug
C=C(c1ccc(C(=O)O)cc1)c1cc2c(cc1C)C(C)(C)CCC2(C)C

Basic Information

ChEMBL ID CHEMBL1023
Name BEXAROTENE
Phase Approved
Structure Type MOL
InChI Key NAVMQTYZDKMPEU-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Bexarotene Bexaroteno LG-100069 LG100069 LGD-1069 LGD1069 NSC-747528 Targretin Targretine
323
Targets
773
Activities
4
Assay Types
5
PK Parameters
20
Publications
9
Known Names
20
Indications
1
Mechanisms

Molecular Properties

348.5
MW (Da)
6.10
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.73
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Topical

Flags

Black Box Warning Natural Product
USAN Stem -arotene
USAN Year 1998

Extended Properties

Molecular Formula C24H28O2
MW 348.49
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.55

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Retinoid X receptor agonist AGONIST Retinoid X receptor

Indications

Lymphoma, T-Cell Lymphoma, T-Cell, Cutaneous Neoplasms Carcinoma, Non-Small-Cell Lung Cognitive Dysfunction Lymphoma Lymphoma, Large-Cell, Anaplastic Mycosis Fungoides Psychotic Disorders Schizophrenia Alopecia Areata Alzheimer Disease Breast Neoplasms Leukemia Leukemia, Myeloid, Acute Lung Neoplasms Myelodysplastic Syndromes Myelodysplastic-Myeloproliferative Diseases Parapsoriasis Psoriasis

ATC Classification

L01XF03
bexarotene
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 678 meas. best 9.18
EC50 59 meas. best 8.57
Ki 24 meas. best 8.23
Kd 12 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SIG-M5
CHEMBL2366251
IC50 9.18 9.18 0.7 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
EC50 8.57 7.5184 2.7 25
Nuclear receptor subfamily 4 group A member 2/Retinoic acid receptor RXR-alpha
CHEMBL3885613
EC50 8.3 8.15 5.0 2
Retinoic acid receptor RXR-beta
CHEMBL1870
Ki 8.23 7.8633 5.9 3
Retinoic acid receptor alpha
CHEMBL2055
EC50 8.22 8.22 6.0 1
Retinoic acid receptor RXR-gamma
CHEMBL2004
Ki 8.08 7.57 8.3 4
Retinoic acid receptor RXR-alpha
CHEMBL2061
Kd 7.85 7.0113 14.0 8
Retinoic acid receptor RXR-alpha
CHEMBL2061
Ki 7.85 7.1789 14.0 9
Retinoic acid receptor RXR-gamma
CHEMBL2004
EC50 7.7 7.5456 20.0 9
Retinoic acid receptor RXR-gamma
CHEMBL4402
EC50 7.7 7.6667 20.0 3
Retinoic acid receptor RXR-beta
CHEMBL4047
Kd 7.68 7.68 21.0 2
Retinoic acid receptor RXR-beta
CHEMBL4047
Ki 7.68 7.68 21.0 1
Retinoic acid receptor RXR-beta
CHEMBL1870
EC50 7.62 7.5356 24.0 9
Retinoic acid receptor RXR-beta
CHEMBL4047
EC50 7.62 7.6067 24.0 3
Retinoic acid receptor RXR-gamma
CHEMBL4402
Kd 7.54 7.54 29.0 2
Retinoic acid receptor RXR-gamma
CHEMBL4402
Ki 7.54 7.54 29.0 1
Retinoic acid receptor RXR-alpha
CHEMBL3084
EC50 7.4 7.4 40.0 1
Retinoic acid receptor RXR-alpha
CHEMBL4431
EC50 7.4 7.4 40.0 1
Retinoic acid receptor beta
CHEMBL2008
Ki 7.3 6.285 50.0 2
DK-MG
CHEMBL1075433
IC50 7.29 7.29 51.2 1
Retinoid X receptor
CHEMBL2363070
EC50 7.28 7.28 52.0 1
Retinoic acid receptor gamma
CHEMBL2003
Ki 6.89 6.19 130.0 2
EKVX
CHEMBL614487
IC50 6.78 6.78 164.7 1
Retinoic acid receptor alpha
CHEMBL2055
Ki 6.75 6.005 180.0 2
Oxysterols receptor LXR-alpha
CHEMBL2808
EC50 6.71 6.71 196.0 1
Retinoic acid receptor beta
CHEMBL2008
EC50 6.55 6.55 282.0 1
RXR alpha/PPAR gamma
CHEMBL2111394
IC50 6.41 6.41 389.0 1
Oxysterols receptor LXR-beta
CHEMBL4093
EC50 6.36 6.36 434.0 1
MV4-11
CHEMBL613835
IC50 6.34 6.34 452.6 1
EW-13
CHEMBL2366124
IC50 6.31 6.31 485.1 1
MEL-HO
CHEMBL1075500
IC50 6.28 6.28 531.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
IC50 6.2 6.2 632.0 1
Retinoic acid receptor gamma
CHEMBL2003
EC50 6.19 6.19 648.0 1
MG-63
CHEMBL614347
IC50 6.1 6.1 788.8 1
OCUB-M
CHEMBL2366121
IC50 5.99 5.99 1021.9 1
LB771-HNC
CHEMBL2366099
IC50 5.6 5.6 2501.2 1
ATN-1
CHEMBL2366277
IC50 5.48 5.48 3341.6 1
ES4
CHEMBL2366118
IC50 5.42 5.42 3768.2 1
CAL-12T
CHEMBL1075406
IC50 5.4 5.4 3962.1 1
PSN1
CHEMBL614241
IC50 5.4 5.4 4004.2 1
NCI-H2122
CHEMBL1075533
IC50 5.31 5.31 4941.1 1
KYSE-180
CHEMBL1075485
IC50 5.3 5.3 5027.3 1
SF-295
CHEMBL614908
IC50 5.29 5.29 5165.9 1
SH-4
CHEMBL2366309
IC50 5.28 5.28 5311.3 1
ALL-PO
CHEMBL2366294
IC50 5.23 5.23 5855.0 1
Cytochrome P450 26B1
CHEMBL3713687
IC50 5.23 5.23 5900.0 1
LoVo
CHEMBL614721
IC50 5.23 5.23 5915.8 1
A-427
CHEMBL614515
IC50 5.22 5.22 5972.5 1
NOS-1
CHEMBL2366141
IC50 5.16 5.16 6917.4 1
TYK-nu
CHEMBL1075601
IC50 5.15 5.15 7109.6 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1910.0 ng/g.hr Mus musculus
AUC 1834.0 ng/g.hr Mus musculus
Cmax 3390.0 nM Homo sapiens
Cmax 1721.71 nM Rattus norvegicus
T1/2 1.2 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SIG-M5 IC50 = 0.6582 nM 9.18 SANGER: Inhibition of human SIG-M5 cell growth in a cell viability assay. -
Retinoic acid receptor RXR-alpha EC50 = 2.7 nM 8.57 Agonist activity at human RXRalpha LBD by cell based luciferase reporter gene as... 21218783
Nuclear receptor subfamily 4 group A member 2/Retinoic acid receptor RXR-alpha EC50 = 5.012 nM 8.3 Inhibition of Nurr1-RXRalpha in HEK293T cells by BRET assay 34251209
Retinoic acid receptor RXR-beta Ki = 5.9 nM 8.23 Selective activity towards retinoid X receptor-beta 9435893
Retinoic acid receptor alpha EC50 = 6.0 nM 8.22 Transcriptional activation in CV-1 cells expressing Retinoic acid receptor RAR a... 10052980
Retinoic acid receptor RXR-gamma Ki = 8.3 nM 8.08 Selective activity towards retinoid X receptor-gamma 9435893
Nuclear receptor subfamily 4 group A member 2/Retinoic acid receptor RXR-alpha EC50 = 10.0 nM 8.0 Agonist activity at Renilla luciferase/GFP2-tagged RXRalpha/Nurr1 (unknown origi... 26820900
Retinoic acid receptor RXR-alpha Kd = 14.0 nM 7.85 Inhibition of [3H]9-cis-RA binding to baculovirus expressed retinoid receptor RX... 8071941
Retinoic acid receptor RXR-alpha Ki = 14.0 nM 7.85 Inhibition of [3H]9-cis-RA binding to RXR alpha receptor -
Retinoic acid receptor RXR-alpha Ki = 16.0 nM 7.8 Selective activity towards retinoid X receptor-alpha 9435893
Retinoic acid receptor RXR-alpha EC50 = 20.0 nM 7.7 Agonist activity at human RXRalpha expressed in African green monkey COS1 cells ... 31160175
Retinoic acid receptor RXR-gamma EC50 = 20.0 nM 7.7 Effective potency in transcriptional activation assay in CV-1 cells expressing R... -
Retinoic acid receptor RXR-gamma EC50 = 20.0 nM 7.7 Transcriptional activity was evaluated in CV-1 cells transfected with expression... 10052980
Retinoic acid receptor RXR-gamma EC50 = 20.0 nM 7.7 Ability to activate gene expression at Retinoic acid receptor RXR-gamma was eval... 7636877
Retinoic acid receptor RXR-alpha EC50 = 20.0 nM 7.7 Agonist activity at RXRalpha (unknown origin) expressed in COS1 cells incubated ... 25815156
Retinoic acid receptor RXR-alpha EC50 = 20.0 nM 7.7 Agonist activity at RXRalpha transfected in human COS1 cells after 18 hrs by luc... 24900241
Retinoic acid receptor RXR-alpha EC50 = 19.8 nM 7.7 Agonist activity at RXRalpha by luciferase reporter gene assay 20656484
Retinoic acid receptor RXR-gamma EC50 = 20.0 nM 7.7 Agonist activity at RXRgamma (unknown origin) 39258574
Retinoic acid receptor RXR-beta Ki = 21.0 nM 7.68 Inhibition of [3H]-9-cis-RA binding to Retinoid X receptor RXR beta -
Retinoic acid receptor RXR-beta Ki = 21.0 nM 7.68 Binding affinity towards recombinantly expressed Retinoic acid receptor RXR-beta... 10052980

Literature References

PubMed DOI Target Context # Activities
29287960 10.1016/j.bmcl.2017.12.033 MDA-MB-231 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
29287960 10.1016/j.bmcl.2017.12.033 BT-549 14
29287960 10.1016/j.bmcl.2017.12.033 MCF7 11
- 10.6019/CHEMBL4689842 HEK-293T 10
24959987 10.1021/np5002016 Molecular identity unknown 7
24959987 10.1021/np5002016 Unchecked 7
- 10.6019/CHEMBL4689842 U2OS 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
32283298 10.1016/j.ejmech.2020.112275 Mus musculus 5
31160175 10.1016/j.bmcl.2019.05.050 ADMET 5
- 10.6019/CHEMBL4689842 Fibroblast 5
28169169 10.1016/j.bmcl.2017.01.066 Oxysterols receptor LXR-alpha 5
24801499 10.1021/jm5004792 Retinoic acid receptor RXR-alpha 4
22712432 10.1021/jm3006806 Retinoic acid receptor RXR-alpha 4
31531208 10.1021/acsmedchemlett.9b00306 Unchecked 4
24959987 10.1021/np5002016 Peroxisome proliferator-activated receptor delta 4
31483660 10.1021/acs.jmedchem.9b00995 Retinoic acid receptor RXR-alpha 4
33356247 10.1021/acs.jmedchem.0c01354 Retinoic acid receptor RXR-alpha 4
32422522 10.1016/j.ejmech.2020.112425 Unchecked 4

Data from ChEMBL 36 via Core Engine