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Compound Detail

CHEMBL1265

ADAPALENE
💊 Approved Drug
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💊 Approved Drug
COc1ccc(-c2ccc3cc(C(=O)O)ccc3c2)cc1C12CC3CC(CC(C3)C1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1265
Name ADAPALENE
Phase Approved
Structure Type MOL
InChI Key LZCDAPDGXCYOEH-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Adapalene Adapalene component of cabtreo Adapalene component of epiduo Adapalene component of idp-126 Adapaleno CD 271 CD-271 Differin
8
Targets
27
Activities
3
Assay Types
1
PK Parameters
20
Publications
8
Known Names
3
Indications
1
Mechanisms

Molecular Properties

412.5
MW (Da)
6.68
ALogP
2
HBA
1
HBD
46.5
PSA (Ų)
0.52
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability OTC
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product
USAN Year 1991

Extended Properties

Molecular Formula C28H28O3
MW 412.53
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness 0.10

Mechanism of Action

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

Indications

Acne Vulgaris Molluscum Contagiosum Skin Diseases

ATC Classification

D10AD03
adapalene
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS
D10AD53
adapalene, combinations
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS

Activity Summary

IC50 14 meas. best 6.39
EC50 7 meas. best 8.7
Ki 6 meas. best 7.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Retinoic acid receptor beta
CHEMBL2008
 EC50 8.7 8.7 2.0 2
Retinoic acid receptor gamma
CHEMBL2003
 EC50 8.52 8.515 3.0 2
Retinoic acid receptor alpha
CHEMBL2055
 EC50 7.66 7.66 22.0 2
Retinoic acid receptor beta
CHEMBL2008
 Ki 7.47 7.47 34.0 2
Retinoic acid receptor gamma
CHEMBL2003
 Ki 6.89 6.89 130.0 2
Unchecked
CHEMBL612545
 IC50 6.39 5.938 405.1 10
Retinoic acid receptor alpha
CHEMBL2055
 Ki 5.96 5.96 1100.0 2
Glycine receptor subunit alpha-1
CHEMBL5845
 EC50 5.89 5.89 1300.0 1
GroEL/GroES
CHEMBL4106139
 IC50 5.68 5.485 2100.0 2
HSP60/HSP10
CHEMBL4106131
 IC50 5.64 5.64 2300.0 1
Aspartate aminotransferase, cytoplasmic
CHEMBL2189139
 IC50 4.66 4.66 21790.0 1

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.0001 - Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Retinoic acid receptor beta EC50 = 2.0 nM 8.7 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Retinoic acid receptor beta EC50 = 2.0 nM 8.7 Agonist activity at GAL4 DNA-binding domain-tagged RARbeta (unknown origin) liga... 29706423
Retinoic acid receptor gamma EC50 = 3.0 nM 8.52 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Retinoic acid receptor gamma EC50 = 3.1 nM 8.51 Agonist activity at GAL4 DNA-binding domain-tagged RARgamma (unknown origin) lig... 29706423
Retinoic acid receptor alpha EC50 = 22.0 nM 7.66 Agonist activity at GAL4 DNA-binding domain-tagged RARalpha (unknown origin) lig... 29706423
Retinoic acid receptor alpha EC50 = 22.0 nM 7.66 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Retinoic acid receptor beta Ki = 34.0 nM 7.47 Binding affinity towards Retinoic acid receptor beta -
Retinoic acid receptor beta Ki = 34.0 nM 7.47 Binding affinity to retinoic acid receptor beta using [3H]CD 367 as radioligand 8544175
Retinoic acid receptor gamma Ki = 130.0 nM 6.89 Binding affinity to retinoic acid receptor (RAR) gamma using [3H]CD 367 as radio... 8544175
Retinoic acid receptor gamma Ki = 130.0 nM 6.89 Binding affinity towards Retinoic acid receptor gamma -
Unchecked IC50 = 405.1 nM 6.39 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 443.5 nM 6.35 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 523.6 nM 6.28 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Unchecked IC50 = 589.65 nM 6.23 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 597.1 nM 6.22 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 787.1 nM 6.1 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Retinoic acid receptor alpha Ki = 1100.0 nM 5.96 Binding affinity towards Retinoic acid receptor alpha -
Retinoic acid receptor alpha Ki = 1100.0 nM 5.96 Binding affinity to retinoic acid receptor alpha using [3H]CD 367 as radioligand 8544175
Unchecked IC50 = 1124.8 nM 5.95 PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Glycine receptor subunit alpha-1 EC50 = 1300.0 nM 5.89 Potentiation of human GlyR-alpha1 expressed in Xenopus laevis oocytes assessed a... 25790278

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4689842 U2OS 9
- 10.6019/CHEMBL4689842 Fibroblast 9
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
30852084 10.1016/j.bmcl.2019.02.028 Unchecked 5
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
- 10.6019/CHEMBL5724696 TERT-RPE1 4
34812616 10.1021/acs.jmedchem.1c01547 Unchecked 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
25790278 10.1021/jm501873p Glycine receptor subunit alpha-1 3
18759424 10.1021/jm800456k MDA-MB-231 2
29706423 10.1016/j.bmcl.2018.04.036 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
18759424 10.1021/jm800456k ADMET 2
18759424 10.1021/jm800456k Unchecked 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2

Data from ChEMBL 36 via Core Engine