8446. Semotiadil

Nomenclature

CAS number: 116476-13-2
(2R)-2-[2-[3-[[2-(1,3-Benzodioxol-5-yloxy)ethyl]methylamino]propoxy]-5-methoxyphenyl]-4-methyl-2H-1,4-benzothiazin-3(4H)-one; (+)-(R)-3,4-dihydro-2-[5-methoxy-2-[3-[N-methyl-[N-2-[3,4-(methylenedioxy)phenoxy]ethyl]amino]propoxy]phenyl]-4-methyl-3-oxo-2H-1,4-benzothiazine; sesamodil; DS-4823.
C29H32N2O6S; mol wt 536.64.
C 64.91%, H 6.01%, N 5.22%, O 17.89%, S 5.98%.

Description and references

Benzothiazine calcium antagonist. Prepn: J. Iwao et al., WO 8700838; eidem, US 4786635 (1987, 1988 both to Santen). Synthesis: M. Fujita et al., J. Med. Chem. 33, 1898 (1990). LC determn in plasma: K. Morishima et al., J. Chromatogr. 527, 381 (1990). Molecular conformation and crystal structure: A. Ota et al., Chem. Pharm. Bull. 41, 1681 (1993). Electrophysiology: N. Miyawaki et al., J. Cardiovasc. Pharmacol. 16, 769 (1990); and antiarrhythmic effects: eidem, Drug Dev. Res. 22, 293 (1991). Antihypertensive effects in rats: A. Kanda, H. Hashimoto, Jpn. J. Pharmacol. 63, 121 (1993). Mechanism of action study: K. Murakami et al., J. Cardiovasc. Pharmacol. 25, 262 (1995).

Chemical structure

Derivative

Fumarate.

Nomenclature

CAS number: 116476-14-3
SD-3211.
C29H32N2O6S.C4H4O4; mol wt 652.71.
C 60.72%, H 5.56%, N 4.29%, O 24.51%, S 4.91%.

Properties

Crystals from EtOH, mp 134-135°. [α]D25 +195° (in DMSO).

Therapeutic Category

Antihypertensive; antianginal.

Keywords

Antianginal; Antihypertensive; Calcium Channel Blocker; Arylalkylamines