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Compound Detail

CHEMBL489

AFIMOXIFENE
🧪 Phase III
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🧪 Phase III
CC/C(=C(\c1ccc(O)cc1)c1ccc(OCCN(C)C)cc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL489
Name AFIMOXIFENE
Phase Phase III
Structure Type MOL
InChI Key TXUZVZSFRXZGTL-QPLCGJKRSA-N

Known Names

4-hydroxytamoxifen 4-OHT Afimoxifene Afimoxifeno Tamogel
12
Targets
77
Activities
3
Assay Types
7
PK Parameters
20
Publications
5
Known Names
3
Indications
2
Mechanisms

Molecular Properties

387.5
MW (Da)
5.70
ALogP
3
HBA
1
HBD
32.7
PSA (Ų)
0.50
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -ifene
USAN Year 2006

Extended Properties

Molecular Formula C26H29NO2
MW 387.52
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -0.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Estrogen receptor modulator MODULATOR Estrogen receptor ✓ ✓
Estrogen-related receptor gamma antagonist ANTAGONIST Estrogen-related receptor gamma ✓ ✓

Indications

Breast Neoplasms Carcinoma, Intraductal, Noninfiltrating Mastodynia

Activity Summary

IC50 67 meas. best 9.28
EC50 8 meas. best 10.01
Ki 2 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
 EC50 10.01 10.01 0.1 1
Estrogen receptor
CHEMBL206
 IC50 9.28 8.4736 0.5 14
Estrogen receptor beta
CHEMBL242
 IC50 9.0 8.74 1.0 3
MCF7
CHEMBL387
 IC50 8.92 5.9642 1.2 19
Ishikawa
CHEMBL614649
 IC50 8.9 8.9 1.3 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.47 6.585 3.4 2
MCF7
CHEMBL387
 EC50 8.46 6.2167 3.5 3
Estrogen receptor
CHEMBL206
 Ki 7.7 7.7 20.0 1
T47D
CHEMBL614361
 IC50 7.62 5.6675 24.0 8
MDA-MB-231
CHEMBL400
 IC50 7.43 5.4125 36.8 4
Estrogen receptor beta
CHEMBL242
 Ki 7.16 7.16 70.0 1
MDA-MB-231
CHEMBL400
 EC50 5.11 5.105 7800.0 2
Unchecked
CHEMBL612545
 IC50 5.06 4.7157 8758.0 7
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.0 5.0 10000.0 1
ADMET
CHEMBL612558
 IC50 5.0 5.0 10000.0 1
Ishikawa
CHEMBL614649
 EC50 4.94 4.94 11500.0 1
Vero
CHEMBL391
 IC50 4.82 4.82 15100.0 1
DU-145
CHEMBL613508
 IC50 4.82 4.82 15300.0 1
MCF-10A
CHEMBL614321
 IC50 4.68 4.672 21000.0 5

Pharmacokinetic Data

Parameter Value Units Species
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 32.0 mL.min-1.kg-1 Rattus norvegicus
CL - - Rattus norvegicus
F 87.0 % Rattus norvegicus
F 94.0 % Rattus norvegicus
Ka 0.25 nM Homo sapiens
Ka 2.03 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor EC50 = 0.0987 nM 10.01 Antagonist activity against ERalpha in estradiol stimulated HEK293T cells measur... 37037140
Estrogen receptor IC50 = 0.53 nM 9.28 Displacement of fluormone-labeled ES2 from recombinant full length human ERalpha... 28105283
Estrogen receptor IC50 = 0.79 nM 9.1 Antagonist activity at FLAG-tagged ERalpha (unknown origin) expressed in HEK293 ... 30940565
Estrogen receptor beta IC50 = 1.0 nM 9.0 Antagonist activity at ERbeta (unknown origin) expressed in human U2OS cells ass... 33904307
Estrogen receptor IC50 = 1.12 nM 8.95 Antagonist activity at ERalpha (unknown origin) 34710747
MCF7 IC50 = 1.2 nM 8.92 Antiproliferative activity against human MCF7 cells 34710747
Ishikawa IC50 = 1.27 nM 8.9 Antiproliferative activity against human Ishikawa cells 34710747
Estrogen receptor IC50 = 1.36 nM 8.87 Antagonist activity at estrogen receptor in human T47D cells incubated for 18 hr... 34251202
Estrogen receptor beta IC50 = 1.68 nM 8.78 Displacement of fluorescent-labeled E2 from LBD of ERbeta (unknown origin) by TR... 33904307
Estrogen receptor IC50 = 2.1 nM 8.68 Binding affinity to GST-tagged human ER alpha ligand-binding domain by TR-FRET a... 30940565
Estrogen receptor IC50 = 2.24 nM 8.65 Displacement of fluorescent-labeled E2 from LBD of ERalpha (unknown origin) by T... 33904307
Estrogen receptor IC50 = 2.3 nM 8.64 Antagonist activity at ERalpha (unknown origin) expressed in human U2OS cells as... 33904307
Estrogen receptor IC50 = 3.0 nM 8.52 Induction of selective estrogen receptor alpha degradation in human MCF7 cells h... 29562737
MCF7 IC50 = 3.3 nM 8.48 Antiproliferative activity against human MCF7 cells after 5 days by coulter coun... 27529700
NON-PROTEIN TARGET IC50 = 3.4 nM 8.47 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability af... 28105283
MCF7 EC50 = 3.5 nM 8.46 Antiproliferative activity against human MCF-7 cells incubated for 72 hrs by Cel... 34251202
Estrogen receptor beta IC50 = 3.61 nM 8.44 Antagonist activity at ERbeta (unknown origin) 34710747
Estrogen receptor IC50 = 3.8 nM 8.42 Antagonist activity at ER-alpha (unknown origin) by ER-alpha coactivator assay 38401456
Estrogen receptor IC50 = 5.6 nM 8.25 Displacement of Fluormone ES2 Green from full-length untagged human ERalpha expr... 30108709
Estrogen receptor IC50 = 7.5 nM 8.12 Displacement of fluorescent labeled-ligand from ERalpha (unknown origin) by comp... 34592434

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 U2OS 320
- 10.6019/CHEMBL5724801 HEK-293T 320
- 10.6019/CHEMBL5724801 Fibroblast 320
- 10.6019/CHEMBL5303304 HEK-293T 8
34710747 10.1016/j.ejmech.2021.113869 Estrogen receptor 8
34710747 10.1016/j.ejmech.2021.113869 MCF7 8
34710747 10.1016/j.ejmech.2021.113869 ADMET 6
- 10.6019/CHEMBL5303304 Fibroblast 6
30940565 10.1016/j.bmc.2019.03.042 Estrogen receptor 6
34710747 10.1016/j.ejmech.2021.113869 Breast carcinoma cell 6
33904307 10.1021/acs.jmedchem.0c02230 Estrogen receptor 5
34251202 10.1021/acs.jmedchem.1c00847 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
38809993 10.1021/acs.jmedchem.4c00196 MCF7 4
37161783 10.1021/acs.jmedchem.2c02032 Unchecked 3
34251202 10.1021/acs.jmedchem.1c00847 Estrogen receptor 3
34251202 10.1021/acs.jmedchem.1c00847 ADMET 3
37037140 10.1016/j.ejmech.2023.115328 Estrogen receptor 3
25198997 10.1021/jm500873e NON-PROTEIN TARGET 3
31746603 10.1021/acs.jmedchem.9b01580 T47D 3

Data from ChEMBL 36 via Core Engine