BRILANESTRANT

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Synonyms
Status
Molecule Category UNKNOWN
UNII 9MM2R1A06R

Structure

InChI Key BURHGPHDEVGCEZ-KJGLQBJMSA-N
Smiles CC/C(=C(/c1ccc(/C=C/C(=O)O)cc1)c1ccc2[nH]ncc2c1)c1ccc(F)cc1Cl
InChI
InChI=1S/C26H20ClFN2O2/c1-2-21(22-10-9-20(28)14-23(22)27)26(18-8-11-24-19(13-18)15-29-30-24)17-6-3-16(4-7-17)5-12-25(31)32/h3-15H,2H2,1H3,(H,29,30)(H,31,32)/b12-5+,26-21+

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H20ClFN2O2
Molecular Weight 446.91
AlogP 6.82
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 65.98
Molecular species ACID
Aromatic Rings 4.0
Heavy Atoms 32.0

Bioactivity

Mechanism of Action Action Reference
Estrogen receptor alpha antagonist ANTAGONIST Other
Protein: Estrogen receptor alpha
Description: Estrogen receptor
Organism : Homo sapiens
P03372 ENSG00000091831
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 3300 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 2200 - - -
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
1-1 1-24 - 0 53
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
- 9 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 1
- 990 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 3400 - - -
Assay Description Organism Bioactivity Reference
Induction of estrogen receptor-alpha degradation in human MCF7 cells after 4 hrs by in-cell western assay Homo sapiens 0.7 nM
Cytotoxicity against human MCF7 cells assessed as cell viability after 5 days by CellTiter-Glo assay Homo sapiens 2.0 nM
In vivo antagonist activity at estrogen receptor in CD-IGS rat uterine assessed as inhibition of estradiol-induced uterine wet weight gain at 1 mg/kg, po administered for 3 days starting at 15 mins post estradiol induction measured on day 4 relative to vehicle-treated control Rattus norvegicus 81.0 %
Displacement of [3H]-E2 from estrogen receptor-alpha (unknown origin) by scintillation counting analysis Homo sapiens 6.1 nM
Displacement of [3H]-E2 from estrogen receptor-beta (unknown origin) by scintillation counting analysis Homo sapiens 8.8 nM
Antagonist activity at estrogen receptor in human MCF7 cells assessed as inhibition of 17beta-estradiol-mediated transcriptional activation after 24 hrs by luciferase reporter gene assay Homo sapiens 2.0 nM
Inhibition of CYP2C8 (unknown origin) Homo sapiens 100.0 nM
Binding affinity to glucocorticoid receptor (unknown origin) Homo sapiens 990.0 nM
Decrease in estrogen receptor alpha level in human MCF7 cells after 4 hrs by in-cell western assay Homo sapiens 0.7 nM
Cytotoxicity against human MCF7 cells assessed as decrease in cell viability after 5 days by celltiterGlo assay Homo sapiens 2.5 nM
Decrease in uterine wet weight of CD-IGS rat at 1 mg/kg, po qd followed 15 mins later administration of 0.1 mg/kg, po 17alpha-ethynylestradiol for 3 consecutive days Rattus norvegicus 79.0 %
Growth inhibition of aromatase inhibitor resistant human MCF7:5C cells assessed as DNA content after 6 days by Hoechst 33258 staining based fluorescence assay Homo sapiens 1.2 nM
Growth inhibition of tamoxifen-sensitive human MCF7:WS8 cells assessed as DNA content after 4 to 5 days by Hoechst 33258 staining based fluorescence assay Homo sapiens 0.2 nM
Induction of ERalpha degradation in tamoxifen-sensitive human MCF7:WS8 cells after 24 hrs by CellTag 700 staining based In-cell western assay Homo sapiens 0.8 nM
Antagonist activity at ERalpha in tamoxifen-sensitive human MCF7:WS8 cells assessed as inhibition of estradiol-induced response after 18 hrs by luciferase reporter gene assay Homo sapiens 11.1 nM
Displacement of [3H]estradiol from full length recombinant human ESR1 expressed in insect cells by radiometric assay Homo sapiens 0.37 nM
Displacement of [3H]estradiol from full length recombinant human ESR1 expressed in insect cells by radiometric assay relative to estradiol Homo sapiens 53.4 %
Induction of selective estrogen receptor alpha degradation in human MCF7 cells harboring TK-ERE-Luc assessed as reduction in estradiol-induced transcriptional activity after 24 hrs by luciferase reporter gene assay Homo sapiens 24.0 nM
Induction of selective estrogen receptor alpha degradation in human MCF7 cells after 18 to 24 hrs by in-cell Western analysis Homo sapiens 0.5 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 35.36 %
Induction of ERalpha degradation in human MCF7 cells in phenol red free RPMI medium containing 5% charcoal-stripped FBS incubated for 4 hrs by IRDye 800CW/DRAQ5 dye based in-cell Western assay Homo sapiens 0.7 nM
Antiproliferative activity against human MCF7 cells assessed as reduction in cell proliferation measured after 5 days by Cell-titer-Glo assay Homo sapiens 2.5 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 5.101 %
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 -0.03 % 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 -0.03 %
Induction of ERalpha degradation in human MCF7 cells after 4 hrs by FITC/Hoechst staining based immunofluorescence imaging analysis Homo sapiens 0.85 nM
Antiproliferative activity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by Celltiter-Glo assay Homo sapiens 44.0 nM
Antiproliferative activity against human T47D cells assessed as reduction in cell viability Homo sapiens 27.0 nM
Induction of ERalpha degradation in human T47D cells Homo sapiens 1.7 nM
Antagonist activity at estrogen receptor in human T47D cells incubated for 18 hrs by ultra high sensitivity luminescence reporter gene assay Homo sapiens 5.31 nM
Antiproliferative activity against human MCF-7 cells incubated for 72 hrs by Cell-titer Glo assay Homo sapiens 17.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL3581693
DrugBank DB12253
FDA SRS 9MM2R1A06R
PubChem 56941241
SureChEMBL SCHEMBL766995
ZINC ZINC000114545220
CONTENTS