8503. Silodosin

Nomenclature

CAS number: 160970-54-7
2,3-Dihydro-1-(3-hydroxypropyl)-5-[(2R)-2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carboxamide; KMD-3213; Rapaflo (Watson); Urief (Kissei).
C25H32F3N3O4; mol wt 495.53.
C 60.60%, H 6.51%, F 11.50%, N 8.48%, O 12.91%.

Description and references

α1a-Adrenoceptor antagonist. Prepn: M. Kitazawa et al., EP 600675; eidem, US 5387603 (1994, 1995 both to Kissei). Adrenoceptor binding study: K. Shibata et al., Mol. Pharmacol. 48, 250 (1995) PubMed; and tissue selectivity: S. Murata et al., J. Urol. 164, 578 (2000) DOI PubMed. Clinical trial in treatment of benign prostatic hyperplasia (BPH): K. Kawabe et al., BJU Int. 98, 1019 (2006) DOI PubMed. Review of pharmacology and clinical experience in BPH: M. Yoshida et al., Expert Opin. Invest. Drugs 16, 1955-1965 (2007) DOI PubMed.

Chemical structure

Properties

White to pale, yellowish white powder, mp 105-109°. [α]D25 -14.0° (c = 1.01 in methanol). Sol in acetic acid, alcohol; very slightly sol in water.

Therapeutic Category

In treatment of benign prostatic hypertrophy.

Keywords

α-Adrenergic Blocker; Antiprostatic Hypertrophy