N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-2H-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide

• ChemBase ID: 4424
• Molecular Formular: C18H15ClN2O6S2
• Molecular Mass: 454.9045
• Monoisotopic Mass: 454.00600589
• SMILES: Clc1c(onc1C)NS(=O)(=O)c1c(scc1)C(=O)Cc1c(cc2OCOc2c1)C
• Canonical 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
• InChIKey: PHWXUGHIIBDVKD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-2H-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide
• IUPAC Traditional name: sitaxentan
• Brand Name: Thelin
• Synonyms: TBC-11251; Sitaxsentan; Sitaxentan

Database IDs

• CAS Number: 210421-64-0
• PubChem SID: 99443241; 160967856
• PubChem CID: 216235

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.386258
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.0911784
• LogD (pH = 7.4): 3.0540793
• Log P: 3.091686
• Molar Refractivity: 105.8045 cm^3
• Polarizability: 41.36925 Å^3
• Polar Surface Area: 107.73 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.35
• LOG S: -4.4
• Solubility (Water): 1.81e-02 g/l

DETAILS

DrugBank - DB06268

• Drug Groups: approved; investigational
• Indication: Investigated for use/treatment in pulmonary hypertension, connective tissue diseases, hypertension, and congestive heart failure.
• Pharmacology: Sitaxentan belongs to a class of drugs known as endothelin receptor antagonists (ERAs). Patients with PAH have elevated levels of endothelin, a potent blood vessel constrictor, in their plasma and lung tissue. Sitaxentan blocks the binding of endothelin to its receptors, thereby negating endothelin's deleterious effects.
• Biotransformation: Hepatic (CYP2C9- and CYP3A4-mediated)
• Absorption: 70-100%
• Half Life: 10 hours
• Protein Binding: 99% +
• Elimination: Renal (50 to 60%); Fecal (40 to 50%)
• External Links: Wikipedia