1353. Bosentan

Nomenclature

CAS number: 147536-97-8
4-(1,1-Dimethylethyl)-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2′-bipyrimidin]-4-yl]benzenesulfonamide; p-tert-butyl-N-[6-(2-hydroxyethoxy)-5-(o-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide; Ro-47-0203.
C27H29N5O6S; mol wt 551.61.
C 58.79%, H 5.30%, N 12.70%, O 17.40%, S 5.81%.

Description and references

Mixed endothelin receptor antagonist. Prepn: K. Burri et al., CA 2071193; eidem, US 5292740 (1992, 1994 both to Hoffmann-La Roche). Receptor binding study: M. Clozel et al., J. Pharmacol. Exp. Ther. 270, 228 (1994). LC-MS determn in plasma: B. Lausecker, G. Hopfgartner, J. Chromatogr. A 712, 75 (1995). Clinical pharmacology: G. Sütsch et al., Cardiovasc. Drugs Ther. 10, 717 (1996). Clinical pharmacokinetics: C. Weber et al., Clin. Pharmacol. Ther. 60, 124 (1996). Clinical trial in hypertension: H. Krum et al., N. Engl. J. Med. 338, 784 (1998); in pulmonary arterial hypertension: L. J. Rubin et al., ibid. 346, 896 (2002).

Chemical structure

Derivative

Monohydrate.

Nomenclature

CAS number: 157212-55-0
Tracleer (Actelion).
C27H29N5O6S.H2O; mol wt 569.63.
C 56.93%, H 5.49%, N 12.29%, O 19.66%, S 5.63%.

Properties

White to yellowish powder. Soly (mg/100 ml): water 1.0; aq soln 0.1 (pH 1.1); 0.1 (pH 4.0); 0.2 (pH 5.0); 43 (pH 7.5).

Derivative

Sodium salt.

Nomenclature

CAS number: 150726-52-6
C27H28N5NaO6S; mol wt 573.60.
C 56.54%, H 4.92%, N 12.21%, Na 4.01%, O 16.74%, S 5.59%.

Properties

mp 195-198°.

Therapeutic Category

Antihypertensive.

Keywords

Endothelin Receptor Antagonist; Antihypertensive