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Compound Detail

CHEMBL2105395

OSPEMIFENE
💊 Approved Drug
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💊 Approved Drug
OCCOc1ccc(/C(=C(/CCCl)c2ccccc2)c2ccccc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2105395
Name OSPEMIFENE
Phase Approved
Structure Type MOL
InChI Key LUMKNAVTFCDUIE-VHXPQNKSSA-N
Therapeutic ✓ Yes

Known Names

(deaminohydroxy) toremifene FC-1271 FC-1271A Ospemifene Ospemifeno Osphena Senshio Tore iii
4
Targets
4
Activities
2
Assay Types
0
PK Parameters
14
Publications
8
Known Names
6
Indications
1
Mechanisms

Molecular Properties

378.9
MW (Da)
5.65
ALogP
2
HBA
1
HBD
29.5
PSA (Ų)
0.41
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -ifene
USAN Year 2006

Extended Properties

Molecular Formula C24H23ClO2
MW 378.90
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.08

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Estrogen receptor modulator MODULATOR Estrogen receptor ✓ ✓

Indications

Atrophic Vaginitis Atrophic Vaginitis Atrophy Dyspareunia Menopause Paget Disease, Extramammary

ATC Classification

G03XC05
ospemifene
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

Drug Warnings

Black Box Warning
vascular toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States
Black Box Warning
neurotoxicity
Country: United States
Black Box Warning
carcinogenicity
Country: United States

Activity Summary

IC50 3 meas. best 5.42
Kd 1 meas. best 4.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Zaire ebolavirus
CHEMBL4513181
 IC50 5.42 5.42 3800.0 1
Unchecked
CHEMBL612545
 Kd 4.7 4.7 19800.0 1
Marburgvirus
CHEMBL4296577
 IC50 4.46 4.46 34350.0 1
MCF7
CHEMBL387
 IC50 4.26 4.26 55000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Zaire ebolavirus IC50 = 3800.0 nM 5.42 Antiviral activity against pseudotyped Ebola virus - Mayinga, Zaire infected in ... 32886512
Unchecked Kd = 19800.0 nM 4.7 Binding affinity to EBOV glycoprotein assessed as dissociation constant by SPR a... 39169825
Marburgvirus IC50 = 34350.0 nM 4.46 Antiviral activity against pseudotyped Marburgvirus-Musoke infected in human A54... 32886512
MCF7 IC50 = 55000.0 nM 4.26 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability af... 25164760

Literature References

PubMed DOI Target Context # Activities
25164760 10.1016/j.ejmech.2014.08.050 MCF7 4
25164760 10.1016/j.ejmech.2014.08.050 MDA-MB-231 3
26972118 10.1016/j.bmcl.2016.03.008 MDA-MB-231 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
32886512 10.1021/acs.jmedchem.0c01001 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
25164760 10.1016/j.ejmech.2014.08.050 MEF 1
26972118 10.1016/j.bmcl.2016.03.008 MCF7 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
32886512 10.1021/acs.jmedchem.0c01001 Zaire ebolavirus 1
32886512 10.1021/acs.jmedchem.0c01001 Marburgvirus 1
39169825 10.1021/acs.jmedchem.4c00527 Unchecked 1

Data from ChEMBL 36 via Core Engine