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Compound Detail

CHEMBL1131

ACITRETIN
💊 Approved Drug
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💊 Approved Drug
COc1cc(C)c(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)c(C)c1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1131
Name ACITRETIN
Phase Approved
Structure Type MOL
InChI Key IHUNBGSDBOWDMA-AQFIFDHZSA-N
Therapeutic ✓ Yes

Known Names

Acitretin Acitretina Acitretine Etretin Neotigason RO 10-1670 RO 10-1670/000 Ro-10-1670-000 RO-10-1670/000 RO-101670000 Soriatane
5
Targets
8
Activities
2
Assay Types
1
PK Parameters
20
Publications
11
Known Names
6
Indications
1
Mechanisms

Molecular Properties

326.4
MW (Da)
5.17
ALogP
2
HBA
1
HBD
46.5
PSA (Ų)
0.58
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -retin
USAN Year 1987

Extended Properties

Molecular Formula C21H26O3
MW 326.44
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 1.38

Mechanism of Action

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

Indications

Psoriasis Psoriasis Alzheimer Disease Dermatitis Melanoma HIV Infections

ATC Classification

D05BB02
acitretin
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS

Drug Warnings

Black Box Warning
teratogenicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States

Activity Summary

IC50 7 meas. best 5.81
Ki 1 meas. best 5.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.81 5.21 1560.0 2
Unchecked
CHEMBL612545
 Ki 5.1 5.1 8000.0 1
ADMET
CHEMBL612558
 IC50 4.84 4.84 14600.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.74 4.58 18200.0 2
Bile salt export pump
CHEMBL2073674
 IC50 4.71 4.71 19700.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
 IC50 4.31 4.31 49000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2000.1 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1560.0 nM 5.81 PUBCHEM_BIOASSAY: High Throughput Screening Assay used to Identify Novel Compoun... -
Unchecked Ki = 8000.0 nM 5.1 Inhibition of Dictyostelium discoideum AX2 RNase P by double reciprocal plot 19216007
ADMET IC50 = 14600.0 nM 4.84 Cytotoxicity against RAMEC assessed as cell viability after 24 hrs by MTT assay 21041094
Bile salt export pump IC50 = 18200.0 nM 4.74 Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells ass... 21965623
Bile salt export pump IC50 = 19700.0 nM 4.71 Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of S... 21965623
Unchecked IC50 = 24730.0 nM 4.61 PUBCHEM_BIOASSAY: A High Throughput Confirmatory Assay used to Identify Novel Co... -
Bile salt export pump IC50 = 38200.0 nM 4.42 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101
ATP-binding cassette sub-family C member 4 IC50 = 49000.0 nM 4.31 Inhibition of human MRP4 overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
490550 10.1021/jm00195a010 Mus musculus 6
299711 10.1021/jm00217a011 Hamster 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.1016/S0960-894X(97)10140-8 MCF7 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
21965623 10.1124/dmd.111.040758 Bile salt export pump 2
23956101 10.1093/toxsci/kft176 Unchecked 2
21041094 10.1016/j.bmc.2010.10.012 Unchecked 2
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 2
21041094 10.1016/j.bmc.2010.10.012 NON-PROTEIN TARGET 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2

Data from ChEMBL 36 via Core Engine