8554. Sitaxsentan

Nomenclature

CAS number: 184036-34-8
N-(4-Chloro-3-methyl-5-isoxazolyl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]-3-thiophenesulfonamide; N-(4-chloro-3-methyl-5-isoxazolyl)-2-[3,4-(methylenedioxy)-6-methyl]phenylacetyl-3-thiophenesulfonamide; IPI-1040; TBC-11251.
C18H15ClN2O6S2; mol wt 454.90.
C 47.53%, H 3.32%, Cl 7.79%, N 6.16%, O 21.10%, S 14.10%.

Description and references

Selective endothelin A (ETA) receptor antagonist. Prepn: M. F. Chan et al., WO 9631492 ; eidem, US 5594021 (1996, 1997 both to Texas Biotech.); C. Wu et al., J. Med. Chem. 40, 1690 (1997). Pharmacology: R. G. Tilton et al., Pulm. Pharmacol. Ther. 13, 87 (2000). Clinical evaluation in heart failure: M. M. Givertz et al., Circulation 101, 2922 (2000); in pulmonary arterial hypertension: D. Langleben et al., Chest 126, 1377 (2004). Review of development and clinical experience in pulmonary arterial hypertension: R. J. Barst, Expert Opin. Pharmacother. 8, 95-109 (2007).

Chemical structure

Properties

Yellow powder, mp 42-45°.

Derivative

Sodium salt.

Nomenclature

CAS number: 210421-74-2
Thelin (Encysive).
C18H14ClNaN2O6S2; mol wt 476.89.
C 45.33%, H 2.96%, Cl 7.43%, Na 4.82%, N 5.87%, O 20.13%, S 13.45%.

Properties

Yellow powder, mp >200° (dec). Sol in water, normal saline, 5% dextrose, and DMSO. Max soly 78 mg/ml at pH >5.5.

Therapeutic Category

In treatment of pulmonary arterial hypertension.

Keywords

Antihypertensive; Endothelin Receptor Antagonist