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Compound Detail

CHEMBL1200666

CALCIPOTRIENE
💊 Approved Drug
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💊 Approved Drug
C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)/C=C/[C@@H](O)C4CC4)CC[C@@H]23)C[C@@H](O)C[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200666
Name CALCIPOTRIENE
Phase Approved
Structure Type MOL
InChI Key LWQQLNNNIPYSNX-UROSTWAQSA-N
Therapeutic ✓ Yes

Known Names

Calcipotriene Calcipotriene component of enstilar Calcipotriene component of taclonex Calcipotriene component of wynzora Calcipotriene hydrate Calcipotriene hydrate component of taclonex Calcipotriene monohydrate Calcipotriol Calcipotriol anhydrous Calcipotriol hydrate Calcipotriol monohydrate Calciptriol +8 more
2
Targets
2
Activities
2
Assay Types
0
PK Parameters
20
Publications
20
Known Names
12
Indications
1
Mechanisms

Molecular Properties

412.6
MW (Da)
5.09
ALogP
3
HBA
3
HBD
60.7
PSA (Ų)
0.55
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem calci-
USAN Year 1992

Extended Properties

Molecular Formula C27H40O3
MW 412.61
Aromatic Rings 0
Heavy Atoms 30
NP-Likeness 2.68

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Vitamin D receptor agonist AGONIST Vitamin D3 receptor ✓ ✓

Indications

Psoriasis Psoriasis Acne Vulgaris Dermatitis, Atopic Eczema Keratosis, Actinic Radiodermatitis Skin Diseases Scleroderma, Localized Scleroderma, Localized Vitiligo Carcinoma, Squamous Cell

ATC Classification

D05AX02
calcipotriol
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS
D05AX52
calcipotriol, combinations
Level 1: DERMATOLOGICALS
Level 2: ANTIPSORIATICS

Activity Summary

IC50 1 meas. best 7.5
Kd 1 meas. best 9.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vitamin D3 receptor
CHEMBL1977
 Kd 9.51 9.51 0.3 1
Homo sapiens
CHEMBL372
 IC50 7.5 7.5 32.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vitamin D3 receptor Kd = 0.31 nM 9.51 Binding affinity to VDR receptor 11462969
Homo sapiens IC50 = 32.0 nM 7.5 Inhibition of growth of human keratinocytes 11462969

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
30579121 10.1016/j.ejmech.2018.12.024 MCF7 7
29407979 10.1016/j.ejmech.2018.01.073 Unchecked 5
30350999 10.1021/acs.jmedchem.8b01165 Mus musculus 4
30350999 10.1021/acs.jmedchem.8b01165 Vitamin D3 receptor 3
38159286 10.1021/acs.jmedchem.3c02102 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 2
15055995 10.1021/jm0310582 Vitamin D3 receptor 2
29407979 10.1016/j.ejmech.2018.01.073 Mus musculus 2
29407979 10.1016/j.ejmech.2018.01.073 Vitamin D3 receptor 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2

Data from ChEMBL 36 via Core Engine