ADAPALENE

Search structure
Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Parent
ATC: D10AD03
UNII: 1L4806J2QF

Structure
InChI Key LZCDAPDGXCYOEH-UHFFFAOYSA-N
Smile COc1ccc(-c2ccc3cc(C(=O)O)ccc3c2)cc1C12CC3CC(CC(C3)C1)C2
InChI
InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)

Physicochemical Descriptors

Property Name Value
Molecular Formula C28H28O3
Molecular Weight 412.53
AlogP 6.68
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 46.53
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 31.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Retinoic acid receptor agonist PubMed PubMed
Primary Target
Retinoic acid receptor-β
Retinoic acid receptor-γ
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Ligand-gated ion channel Glycine receptor
1300 - - - -
Other cytosolic protein
- 2300 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 1
22 - - 1100-1100 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 2
2 - - 34-34 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 3
3 - - 130-130 -
Unclassified protein
- 2100-5100 - - 98-99

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Skin Diseases 1 D012871 ClinicalTrials

Related Entries

Scaffolds

Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Pain 28.5
Skin and subcutaneous tissue disorders Erythema 26.1
General disorders and administration site conditions Pain 14.2
Skin and subcutaneous tissue disorders Dry skin 14.0
Skin and subcutaneous tissue disorders Erythema 13.0
Skin and subcutaneous tissue disorders Dry skin 10.8
Skin and subcutaneous tissue disorders Dry skin 7.7
Skin and subcutaneous tissue disorders Skin discomfort 6.44
Skin and subcutaneous tissue disorders Skin discomfort 5.81
Skin and subcutaneous tissue disorders Skin discomfort 5.8
Immune system disorders Dermatitis contact 5.43
Skin and subcutaneous tissue disorders Dry skin 3.96
General disorders and administration site conditions Pain 3.6
Skin and subcutaneous tissue disorders Dry skin 3.0
Skin and subcutaneous tissue disorders Skin discomfort 2.73
Skin and subcutaneous tissue disorders Skin exfoliation 2.58
Skin and subcutaneous tissue disorders Erythema 2.48
Immune system disorders Dermatitis contact 2.26
Skin and subcutaneous tissue disorders Photosensitivity reaction 2.0
Injury, poisoning and procedural complications Sunburn 2.0
Skin and subcutaneous tissue disorders Photosensitivity reaction 1.93
Injury, poisoning and procedural complications Sunburn 1.93
Skin and subcutaneous tissue disorders Pruritus 1.9
Skin and subcutaneous tissue disorders Pruritus 1.66
Skin and subcutaneous tissue disorders Skin irritation 1.61
Skin and subcutaneous tissue disorders Skin exfoliation 1.6
Skin and subcutaneous tissue disorders Skin exfoliation 1.55
Skin and subcutaneous tissue disorders Dry skin 1.49
Skin and subcutaneous tissue disorders Photosensitivity reaction 1.49
Injury, poisoning and procedural complications Sunburn 1.49
Skin and subcutaneous tissue disorders Erythema 1.23
Skin and subcutaneous tissue disorders Photosensitivity reaction 1.2
Injury, poisoning and procedural complications Sunburn 1.2
General disorders and administration site conditions Pain 1.0
Skin and subcutaneous tissue disorders Skin irritation 1.0
Skin and subcutaneous tissue disorders Photosensitivity reaction 0.965
Injury, poisoning and procedural complications Sunburn 0.965
Skin and subcutaneous tissue disorders Skin discomfort 0.9
Skin and subcutaneous tissue disorders Photosensitivity reaction 0.889
Skin and subcutaneous tissue disorders Pruritus 0.889
Injury, poisoning and procedural complications Sunburn 0.889
Skin and subcutaneous tissue disorders Skin exfoliation 0.615
Skin and subcutaneous tissue disorders Photosensitivity reaction 0.6
Injury, poisoning and procedural complications Sunburn 0.6
Skin and subcutaneous tissue disorders Erythema 0.4
Skin and subcutaneous tissue disorders Dry skin 0.322
Skin and subcutaneous tissue disorders Skin discomfort 0.322
Skin and subcutaneous tissue disorders Skin irritation 0.273

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Skin and subcutaneous tissue disorders
72.03
Nervous system disorders
10.62
Injury, poisoning and procedural complications
8.06
General disorders and administration site conditions
3.92
Immune system disorders
3.45

Cross References

Resources Reference
CAS NUMBER 106685-40-9
ChEBI 31174
ChEMBL CHEMBL1265
DrugBank DB00210
DrugCentral 87
EPA CompTox DTXSID5046481
FDA SRS 1L4806J2QF
Human Metabolome Database HMDB0014355
Guide to Pharmacology 5429
KEGG D01112
PharmGKB PA448047
PubChem 60164
SureChEMBL SCHEMBL2747
ZINC ZINC000003784182
CONTENTS