SITAXENTAN

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Synonyms
Status
Molecule Category Free-form
ATC C02KX03
UNII J9QH779MEM
EPA CompTox DTXSID0057673

Structure

InChI Key PHWXUGHIIBDVKD-UHFFFAOYSA-N
Smiles Cc1cc2c(cc1CC(=O)c1sccc1S(=O)(=O)Nc1onc(C)c1Cl)OCO2
InChI
InChI=1S/C18H15ClN2O6S2/c1-9-5-13-14(26-8-25-13)7-11(9)6-12(22)17-15(3-4-28-17)29(23,24)21-18-16(19)10(2)20-27-18/h3-5,7,21H,6,8H2,1-2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H15ClN2O6S2
Molecular Weight 454.91
AlogP 3.96
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 107.73
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 29.0

Bioactivity

Mechanism of Action Action Reference
Endothelin receptor, ET-A/ET-B antagonist ANTAGONIST PubMed PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Endothelin receptor
- 1-1 - 0 -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 12600 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 28400 - - -
Assay Description Organism Bioactivity Reference
Displacement of [125I]ET-1 from Endothelin A receptor None 1.4 nM
Binding affinity towards Endothelin A receptor None 0.43 nM
Inhibitory concentration towards endothelin B receptor in human None 9.8 nM
In vitro inhibition of endothelin binding to human Endothelin A receptor using [125I]-labeled ET-1 competition assay None 1.4 nM
Inhibitory concentration towards Endothelin A receptor in human None 1.4 nM
Inhibitory concentration was determined against selective Endothelin A receptor None 1.4 nM
Binding affinity against human Endothelin A receptor None 0.43 nM
In vivo efficacy in acute hypoxia induced pulmonary hypertension in rats following intravenous administration Rattus norvegicus 0.5 mg kg-1
In vivo efficacy in acute hypoxia induced pulmonary hypertension in rats following oral administration Rattus norvegicus 1.0 mg kg-1
The compound was tested in vivo for percent inhibition in ET-1 challenge in rats at 15 mg/kg Rattus norvegicus 41.0 %
Inhibition of ET1 induced stimulation of phosphoinositide turnover Rattus norvegicus 0.686 nM
Phosphoinositol hydrolysis in TE671 or transfected cos 7 cells None 10.0 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 16.31 %
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 -0.13 % 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 -0.13 %

Cross References

Resources Reference
ChEBI 135736
ChEMBL CHEMBL282724
DrugBank DB06268
DrugCentral 3548
FDA SRS J9QH779MEM
Human Metabolome Database HMDB0015629
Guide to Pharmacology 3950
PharmGKB PA165958361
PubChem 216235
SureChEMBL SCHEMBL803344
ZINC ZINC000001481831
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