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Compound Detail

CHEMBL1657

TAZAROTENE
💊 Approved Drug
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💊 Approved Drug
CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CCS3)nc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1657
Name TAZAROTENE
Phase Approved
Structure Type MOL
InChI Key OGQICQVSFDPSEI-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1201375

Known Names

AGN 190168 AGN-190168 AGN190168 Arazlo Avage Fabior Idp-123 Tazarotene Tazarotene component of duobrii Tazarotene component of idp-118 Tazaroteno Tazorac +1 more
4
Targets
7
Activities
2
Assay Types
0
PK Parameters
20
Publications
13
Known Names
9
Indications
1
Mechanisms

Molecular Properties

351.5
MW (Da)
4.43
ALogP
4
HBA
0
HBD
39.2
PSA (Ų)
0.59
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Prescription
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product Prodrug
USAN Stem -arotene
USAN Year 1994

Extended Properties

Molecular Formula C21H21NO2S
MW 351.47
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.65

Mechanism of Action

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

Indications

Acne Vulgaris Hypopigmentation Lentigo Psoriasis Psoriasis Idiopathic Pulmonary Fibrosis Skin Diseases Skin Neoplasms Lymphoma, T-Cell, Cutaneous

ATC Classification

D05AX05
tazarotene
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS

Activity Summary

EC50 6 meas. best 9.1
IC50 1 meas. best 5.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Retinoic acid receptor beta
CHEMBL2008
 EC50 9.1 9.1 0.8 2
Retinoic acid receptor gamma
CHEMBL2003
 EC50 7.4 7.4 40.0 2
Retinoic acid receptor alpha
CHEMBL2055
 EC50 7.2 7.2 63.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 5.5 5.5 3150.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Retinoic acid receptor beta EC50 = 0.8 nM 9.1 Activity at human RARbeta ligand binding domain expressed in COS7 cells co-trans... 19058965
Retinoic acid receptor beta EC50 = 0.8 nM 9.1 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Retinoic acid receptor gamma EC50 = 40.0 nM 7.4 Activity at human RARgamma ligand binding domain expressed in COS7 cells co-tran... 19058965
Retinoic acid receptor gamma EC50 = 40.0 nM 7.4 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Retinoic acid receptor alpha EC50 = 63.0 nM 7.2 Activity at human RARalpha ligand binding domain expressed in COS7 cells co-tran... 19058965
Retinoic acid receptor alpha EC50 = 63.0 nM 7.2 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Cytochrome P450 3A4 IC50 = 3150.0 nM 5.5 Inhibition Assay: Compounds were assessed for inhibition (IC50, n=2) of CYP2C8, ... -

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 9
- 10.6019/CHEMBL4689842 U2OS 8
- 10.6019/CHEMBL4689842 Fibroblast 5
- 10.6019/CHEMBL5724696 TERT-RPE1 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
19058965 10.1016/j.bmcl.2008.11.040 Retinoic acid receptor alpha 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
19058965 10.1016/j.bmcl.2008.11.040 Retinoic acid receptor gamma 2

Data from ChEMBL 36 via Core Engine