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Compound Detail

CHEMBL25202

TAMIBAROTENE
💊 Approved Drug
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💊 Approved Drug
CC1(C)CCC(C)(C)c2cc(NC(=O)c3ccc(C(=O)O)cc3)ccc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL25202
Name TAMIBAROTENE
Phase Approved
Structure Type MOL
InChI Key MUTNCGKQJGXKEM-UHFFFAOYSA-N

Known Names

AM-80 Am80 Amnoid INNO-507 NSC-608000 OP-01 RR-110 Sy-1425 Tamibarotene Tamibaroteno TM-411 TOS-80T
12
Targets
23
Activities
4
Assay Types
0
PK Parameters
20
Publications
12
Known Names
10
Indications
2
Mechanisms

Molecular Properties

351.4
MW (Da)
4.99
ALogP
2
HBA
2
HBD
66.4
PSA (Ų)
0.82
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2005
Availability Unknown
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -arotene
USAN Year 2021

Extended Properties

Molecular Formula C22H25NO3
MW 351.45
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.33

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Retinoic acid receptor beta agonist AGONIST Retinoic acid receptor beta ✓ ✓
Retinoic acid receptor alpha agonist AGONIST Retinoic acid receptor alpha ✓ ✓

Indications

Myelodysplastic Syndromes Alzheimer Disease Crohn Disease Leukemia, Myeloid, Acute Leukemia, Promyelocytic, Acute Lupus Nephritis Paraparesis, Tropical Spastic Polycystic Kidney, Autosomal Dominant Leukemia, Myelomonocytic, Chronic Pancreatic Neoplasms

Activity Summary

IC50 13 meas. best 7.11
EC50 6 meas. best 7.35
Kd 2 meas. best 5.86
Ki 2 meas. best 8.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Retinoic acid receptor alpha
CHEMBL2055
 Ki 8.19 8.19 6.5 1
Retinoic acid receptor beta
CHEMBL2008
 Ki 7.52 7.52 30.0 1
Retinoic acid receptor alpha
CHEMBL2055
 EC50 7.35 7.325 45.0 2
Retinoic acid receptor alpha
CHEMBL2055
 IC50 7.11 7.11 78.0 1
Retinoic acid receptor beta
CHEMBL2008
 EC50 6.7 6.665 200.0 2
Retinoic acid receptor gamma
CHEMBL2003
 EC50 6.23 6.225 591.0 2
Flavin reductase (NADPH)
CHEMBL5019
 Kd 5.86 5.86 1380.0 2
NB-4
CHEMBL614188
 IC50 5.32 5.32 4810.0 2
HL-60
CHEMBL383
 IC50 5.22 5.1067 6000.0 3
Cytochrome P450 3A4
CHEMBL340
 IC50 4.97 4.97 10650.0 1
Cytochrome P450 26A1
CHEMBL5141
 IC50 4.88 4.88 13050.0 1
Jurkat
CHEMBL397
 IC50 4.76 4.76 17300.0 1
MOLT-4
CHEMBL614177
 IC50 4.71 4.71 19500.0 1
U-937
CHEMBL612794
 IC50 4.7 4.7 20200.0 1
K562
CHEMBL385
 IC50 4.37 4.37 42370.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Retinoic acid receptor alpha Ki = 6.5 nM 8.19 Agonistic activity towards retinoic acid receptor-alpha 9435893
Retinoic acid receptor beta Ki = 30.0 nM 7.52 Agonistic activity towards retinoic acid receptor-beta 9435893
Retinoic acid receptor alpha EC50 = 45.0 nM 7.35 Agonist activity at RARalpha 20925433
Retinoic acid receptor alpha EC50 = 50.0 nM 7.3 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Retinoic acid receptor alpha IC50 = 78.0 nM 7.11 Binding affinity for Retinoic Acid Receptor alpha (RAR alpha) 10669568
Retinoic acid receptor beta EC50 = 200.0 nM 6.7 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Retinoic acid receptor beta EC50 = 235.0 nM 6.63 Agonist activity at RARbeta 20925433
Retinoic acid receptor gamma EC50 = 591.0 nM 6.23 Agonist activity at RARgamma 20925433
Retinoic acid receptor gamma EC50 = 600.0 nM 6.22 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Flavin reductase (NADPH) Kd = 1380.0 nM 5.86 Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLV... 34957824
Flavin reductase (NADPH) Kd = 1380.38 nM 5.86 Binding affinity to human N-terminal His6-tagged and thrombin cleavage fused BLV... 34957824
NB-4 IC50 = 4810.0 nM 5.32 Cytotoxicity against Homo sapiens (human) NB4 cells assessed as growth inhibitio... -
NB-4 IC50 = 4810.0 nM 5.32 Antiproliferative activity against human NB4 cells after 48 hrs by MTT assay 22014829
HL-60 IC50 = 6000.0 nM 5.22 Antiproliferative activity against human HL60 cells 19443225
HL-60 IC50 = 8940.0 nM 5.05 Antiproliferative activity against human HL60 cells after 48 hrs by MTT assay 22014829
HL-60 IC50 = 8940.0 nM 5.05 Cytotoxicity against Homo sapiens (human) HL60 cells assessed as growth inhibiti... -
Cytochrome P450 3A4 IC50 = 10650.0 nM 4.97 Inhibition Assay: Compounds were assessed for inhibition (IC50, n=2) of CYP2C8, ... -
Cytochrome P450 26A1 IC50 = 13050.0 nM 4.88 Inhibition Assay: Eighteen compounds were tested as potential inhibitors of CYP2... -
Jurkat IC50 = 17300.0 nM 4.76 Antiproliferative activity against human Jurkat cells 19443225
MOLT-4 IC50 = 19500.0 nM 4.71 Antiproliferative activity against human MOLT4 cells 19443225

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4689842 U2OS 8
- 10.6019/CHEMBL4689842 Fibroblast 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
34957824 10.1021/acs.jmedchem.1c01664 Flavin reductase (NADPH) 5
- 10.6019/CHEMBL5724696 TERT-RPE1 4
11392543 10.1016/s0960-894x(01)00204-9 HL-60 4
11392543 10.1016/s0960-894x(01)00204-9 Retinoic acid receptor alpha 4
11392543 10.1016/s0960-894x(01)00204-9 Retinoic acid receptor beta 4
10669568 10.1021/jm990063w Retinoic acid receptor alpha 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
23217961 10.1016/j.bmcl.2012.11.008 HL-60 2
2795600 10.1021/jm00130a011 HL-60 2
23493449 10.1021/ml300366t U-937 2
23685180 10.1016/j.bmc.2013.04.053 HL-60 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
8182710 10.1021/jm00036a017 HL-60 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2

Data from ChEMBL 36 via Core Engine