791. Arotinolol

Nomenclature

CAS number: 68377-92-4
5-[2-[[3-[(1,1-Dimethylethyl)amino]-2-hydroxypropyl]thio]-4-thiazolyl]-2-thiophenecarboxamide; 2-(3′-tert-butylamino-2′-hydroxypropylthio)-4-(5′-carbamoyl-2′-thienyl)thiazole.
C15H21N3O2S3; mol wt 371.54.
C 48.49%, H 5.70%, N 11.31%, O 8.61%, S 25.89%.

Description and references

Propanolamine deriv with α- and β-adrenergic blocking activity. Prepn: T. Hibino et al., DE 2341753; eidem, US 3932400 (1974, 1976 both to Sumitomo); Y. Hara et al., J. Pharm. Sci. 67, 1334 (1978). Characterization of adrenoceptor blocking effects in vivo: A. Miyagishi et al., Arch. Int. Pharmacodyn. Ther. 271, 249 (1984). Possible antianginal effects: M. Sakanashi et al., Oyo Yakuri 28, 709 (1984); C.A. 102, 39669z (1985). Long-term antihypertensive effect in rats: K. Kishi et al., J. Pharmacobio-Dyn. 8, 50 (1985). Comparison with timolol, q.v., of effect on intraocular pressure and hemodynamics: M. Nakashima et al., Eur. J. Clin. Pharmacol. 28, 391 (1985).

Chemical structure

Properties

Crystals from chloroform/petroleum ether, mp 148-149°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 68377-91-3
S-596; ARL; Almarl (Sumitomo).
C15H21N3O2S3.HCl; mol wt 408.00.
C 44.16%, H 5.43%, N 10.30%, O 7.84%, S 23.58%, Cl 8.69%.

Properties

Crystals from methanol/water, mp 234-235.5° (dec). LD50 in mice (mg/kg): 86 i.v., >360 i.p., >5000 orally (Hara).

Therapeutic Category

Antihypertensive; antianginal; antiarrhythmic.

Keywords

α-Adrenergic Blocker; β-Adrenergic Blocker; Antianginal; Antiarrhythmic; Antihypertensive; Aryloxypropanolamine Derivatives