BREXANOLONE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
UNII S39XZ5QV8Y
EPA CompTox DTXSID1046342

Structure

InChI Key AURFZBICLPNKBZ-SYBPFIFISA-N
Smiles CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H34O2
Molecular Weight 318.5
AlogP 4.6
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 37.3
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 23.0

Bioactivity

Mechanism of Action Action Reference
GABA-A receptor; anion channel positive allosteric modulator POSITIVE ALLOSTERIC MODULATOR FDA
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit pi
Organism : Homo sapiens
O00591 ENSG00000094755
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit delta
Organism : Homo sapiens
O14764 ENSG00000187730
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-1
Organism : Homo sapiens
P14867 ENSG00000022355
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-1
Organism : Homo sapiens
P18505 ENSG00000163288
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-2
Organism : Homo sapiens
P18507 ENSG00000113327
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-3
Organism : Homo sapiens
P28472 ENSG00000166206
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-5
Organism : Homo sapiens
P31644 ENSG00000186297
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-3
Organism : Homo sapiens
P34903 ENSG00000011677
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-2
Organism : Homo sapiens
P47869 ENSG00000151834
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit beta-2
Organism : Homo sapiens
P47870 ENSG00000145864
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-4
Organism : Homo sapiens
P48169 ENSG00000109158
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit epsilon
Organism : Homo sapiens
P78334 ENSG00000102287
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit alpha-6
Organism : Homo sapiens
Q16445 ENSG00000145863
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-1
Organism : Homo sapiens
Q8N1C3 ENSG00000163285
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit gamma-3
Organism : Homo sapiens
Q99928 ENSG00000182256
Protein: GABA-A receptor; anion channel
Description: Gamma-aminobutyric acid receptor subunit theta
Organism : Homo sapiens
Q9UN88 ENSG00000268089
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 66000 - - -
Ion channel Ligand-gated ion channel GABA-A receptor
160-237 51-2610 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 42
Assay Description Organism Bioactivity Reference
Ability to allosterically modulate the binding of [35S]TBPS to gamma-aminobutyric-acid A receptor in rat brain cortical P2 membranes. Rattus norvegicus 51.0 nM
Non-competitive displacement of [35S]TBPS from picrotoxin binding site found in heterogeneous Gamma-aminobutyric acid A receptor in rat brain membranes Rattus norvegicus 74.0 nM
In vitro binding affinity to the Gamma-aminobutyric acid A receptor complex in presence of GABA in rat cerebellum tissue None 80.0 nM
Inhibition of binding of tert-butyl bicyclophosphorothionate ([35 S]TBPS) at Gamma-aminobutyric acid A receptor from rat whole brain membranes None 155.0 nM
The concentration required to inhibit 50% of binding of [35S]TBPS to Gamma-aminobutyric acid A receptor to rat whole brain membranes. None 91.0 nM
Displacement of [3S]-tert-butylbicyclophosphorothionate (TBPS) from Gamma-aminobutyric acid A (GABA-A) receptor of rat brain membranes Rattus norvegicus 74.0 nM
Potentiation of GABA-activated currents in Xenopus oocytes expressing cloned human alpha-1-beta-2-gamma-2L subunits of GABA-A receptor Homo sapiens 160.0 nM
Displacement of [35S]TBPS from picrotoxin site of GABA-A receptor of rat brain membranes Rattus norvegicus 74.0 nM
Increase in [3H]flunitrazepam binding to GABA-A receptor in mouse embryo cortical neurons Mus musculus 870.96 nM
Displacement of [35S]TBPS from GABA-A receptor in rat brain membrane Rattus norvegicus 74.0 nM
Displacement of [3H]TBOB from GABAA receptor in Sprague-Dawley rat cerebral cortex Rattus norvegicus 329.0 nM
Displacement of [35S]TPBS from GABAA receptor in rat brain Rattus norvegicus 74.0 nM
Anesthetic effect in Xenopus laevis assessed as loss of righting response Xenopus laevis 420.0 nM
Displacement of [35S]TBPS from Wistar rat brain GABAA receptor Rattus norvegicus 80.0 nM
Displacement of [3H]ethynylpropylbicycloorthobenzoate from GABAA receptor from rat cortical membrane by scintillation counting in presence of 1 uM GABA Rattus norvegicus 140.0 nM
Inhibition of [35S]tert-butylbicyclo[ 2.2.2]phosphorothionate binding to GABAA receptor in Wistar rat brain membrane Rattus norvegicus 80.0 nM
Inhibition of glutamate-induced excitotoxicity in rat E18 cells assessed as reduction in cell death at 80 uM pretreated for 24 hrs before glutamate challenge measured after 24 hrs by MTT assay Rattus norvegicus 40.0 %
Inhibition of glutamate-induced excitotoxicity in rat E18 cells assessed as reduction in cell death at 5 uM pretreated for 24 hrs before glutamate challenge measured after 24 hrs by MTT assay Rattus norvegicus -3.0 %
Displacement of [35S]TBPS from GABAA receptor in rat cerebellum after 60 mins Rattus norvegicus 80.0 nM
Displacement of [35S]TBPS from GABAA receptor picrotoxin binding site in rat brain membranes Rattus norvegicus 74.0 nM
Anesthetic effect on Xenopus laevis tadpole assessed as loss of righting reflex Xenopus laevis 420.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 41.5 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 89.68 %
Anesthetic effect on prelimb-bud stage Xenopus laevis tadpole assessed as loss of righting reflex after 3 hrs Xenopus laevis 420.0 nM
Displacement of [35S]TBPS from rat picrotoxin binding site of GABAA receptor after 2 hrs by scintillation counting analysis Rattus norvegicus 74.0 nM
Displacement of [3H]TBPS from GABAA receptor in Sprague-Dawley rat brain cortical membrane after 90 mins by liquid scintillation spectrometry Rattus norvegicus 22.0 nM
Positive allosteric modulation of recombinant alpha1beta2gamma2 GABAA receptor (unknown origin) expressed in LTK cells assessed as potentiation of GABA-induced channel current treated for 30 s prior to GABA stimulation for 2s by Q-patch assay Homo sapiens 237.0 nM
Positive allosteric modulation of recombinant alpha4beta3delta GABAA receptor (unknown origin) expressed in CHO cells assessed as potentiation of GABA-induced channel current treated for 30 s prior to GABA stimulation for 2s by manual patch assay Homo sapiens 75.5 nM
Displacement of [35S]TBPS from GABA-A receptor in Sprague-Dawley rat cerebral cortex cell membranes after 90 mins in presence of GABA by liquid scintillation counting Rattus norvegicus 22.0 nM
Positive allosteric modulation of GABAA receptor alpha1beta2gamma2 (unknown origin) expressed in mouse LTK cells assessed as potentiation of GABA-mediated increase in channel current under holding potential at -80 mV preincubated for 30 secs followed by GABA stimulation for 2 secs by automated patch clamp assay Homo sapiens 237.0 nM
Positive allosteric modulation of GABAA receptor alpha4beta3delta (unknown origin) expressed in CHO cells assessed as potentiation of GABA-mediated increase in channel current under holding potential at -80 mV preincubated for 30 secs followed by GABA stimulation for 2 secs by manual patch clamp assay Homo sapiens 75.5 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 4.22 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 1.14 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 21.12 %
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 0.75 % 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 0.63 % 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 0.75 % 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 0.63 %

Related Entries

Cross References

Resources Reference
ChEBI 50169
ChEMBL CHEMBL207538
DrugBank DB11859
FDA SRS S39XZ5QV8Y
Human Metabolome Database HMDB0001449
Guide to Pharmacology 4108
KEGG C13712
PubChem 92786
SureChEMBL SCHEMBL588060
ZINC ZINC000004081043
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