sitaxsentan   Click here for help

GtoPdb Ligand ID: 3950

Synonyms: TBC11251 / TBC-11251 | Thelin®
Approved drug
sitaxsentan is an approved drug
Compound class: Synthetic organic
Comment: Sitaxentan sodium (as a component of the product Thelin) appears to be approved for use in only Canada and the UK.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 144.35
Molecular weight 454.01
XLogP 3.04
No. Lipinski's rules broken 0
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Canonical SMILES O=C(c1sccc1S(=O)(=O)Nc1onc(c1Cl)C)Cc1cc2OCOc2cc1C
Isomeric SMILES O=C(c1sccc1S(=O)(=O)Nc1onc(c1Cl)C)Cc1cc2OCOc2cc1C
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
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Summary of Clinical Use Click here for help
Use of sitaxentan was indicated for the treatment of pulmonary hypertension, connective tissue diseases, hypertension and congestive heart failure. However, use of sitaxentan has been discontinued in most countries due to concerns about liver toxicity.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Competitive antagonist of endothelin-1 at endothelin-A and -B receptors. The binding of endothelin-1 at these receptors causes pulmonary vaoconstriction therefore their antagonism by sitaxentan decreases pulmonary vascular resistance.