LASOFOXIFENE

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Synonyms
Status
Molecule Category UNKNOWN
ATC G03XC03
UNII 337G83N988
EPA CompTox DTXSID50171037

Structure

InChI Key GXESHMAMLJKROZ-IAPPQJPRSA-N
Smiles Oc1ccc2c(c1)CC[C@H](c1ccccc1)[C@@H]2c1ccc(OCCN2CCCC2)cc1
InChI
InChI=1S/C28H31NO2/c30-24-11-15-27-23(20-24)10-14-26(21-6-2-1-3-7-21)28(27)22-8-12-25(13-9-22)31-19-18-29-16-4-5-17-29/h1-3,6-9,11-13,15,20,26,28,30H,4-5,10,14,16-19H2/t26-,28+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C28H31NO2
Molecular Weight 413.56
AlogP 5.73
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 32.7
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 31.0

Bioactivity

Mechanism of Action Action Reference
Estrogen receptor modulator MODULATOR Other
Protein: Estrogen receptor
Description: Estrogen receptor
Organism : Homo sapiens
P03372 ENSG00000091831
Protein: Estrogen receptor
Description: Estrogen receptor beta
Organism : Homo sapiens
Q92731 ENSG00000140009
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 1
- 1-4 - - 26-74
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 2
- 2-24 - - 26-74
Assay Description Organism Bioactivity Reference
Inhibition of estradiol binding to estrogen receptor Rattus norvegicus 11.1 nM Inhibition of estradiol binding to estrogen receptor Rattus norvegicus 11.3 nM
Binding affinity for human estrogen receptor beta Homo sapiens 1.8 nM
Binding affinity for human estrogen receptor alpha Homo sapiens 1.3 nM
Inhibition of [3H]estradiol binding to human estrogen receptor beta expressed in HeLa cells Homo sapiens 13.0 nM
Inhibition of [3H]estradiol binding to human estrogen receptor alpha expressed in HeLa cells Homo sapiens 4.0 nM
Inhibition of 17-beta-estradiol mediated luciferase transcription in HeLa cells expressing human estrogen receptor beta; ERE assay Homo sapiens 24.0 nM
Inhibition of 17-beta-estradiol mediated luciferase transcription in HeLa cells expressing human estrogen receptor alpha; ERE assay Homo sapiens 3.1 nM
Inhibition of MCF-7 cell proliferation Homo sapiens 0.1 nM
Inhibition of estrogen-mediated human breast adenocarcinoma (MCF-7) cell proliferation Homo sapiens 2.3 nM
Estrogenic effect in rat uterine weight assay Rattus norvegicus 26.0 %
Anti-estrogenic effect in rat uterine weight assay Rattus norvegicus 74.0 %
Inhibition of binding to recombinant human ERalpha by scintillation proximity assay Homo sapiens 1.4 nM
Inhibition of binding to recombinant human ERbeta by scintillation proximity assay Homo sapiens 1.8 nM
Antiproliferative activity against human breast cancer MCF7 cell line in presence of 0.003 nM estradiol Homo sapiens 0.1 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 54.26 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 26.21 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.843 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.39 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.39 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.39 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.39 %

Cross References

Resources Reference
ChEBI 135938
ChEMBL CHEMBL328190
DrugBank DB06202
FDA SRS 337G83N988
Guide to Pharmacology 7542
PDB C3D
PubChem 216416
SureChEMBL SCHEMBL26815
ZINC ZINC000003918428
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