19. Acebutolol

Nomenclature

CAS number: 37517-30-9
N-[3-Acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide; 3′-acetyl-4′-[2-hydroxy-3-(isopropylamino)propoxy]butyranilide; 1-(2-acetyl-4-n-butyramidophenoxy)-2-hydroxy-3-isopropylaminopropane; 5′-butyramido-2′-(2-hydroxy-3-isopropylaminopropoxy)acetophenone.
C18H28N2O4; mol wt 336.43.
C 64.26%, H 8.39%, N 8.33%, O 19.02%.

Description and references

Cardioselective β-adrenergic blocker. Prepn: K. R. H. Wooldridge, B. Basil, ZA 6808345; eidem, US 3857952 (1969, 1974 both to May & Baker). Pharmacology: Cuthbert, Owusu-Ankomah, Br. J. Pharmacol. 43, 639 (1971) PubMed; Basil et al., Br. J. Pharmacol. 48, 198 (1973) PubMed; Lewis et al., Br. Heart J. 35, 743 (1973) DOI PubMed. HPLC determn in plasma and urine: M. Piquette-Miller et al., J. Chromatogr. 526, 129 (1990) DOI PubMed. Crystal structure: A. Carpy et al., Acta Crystallogr. B35, 185 (1979). Review of pharmacology and therapeutic efficacy: B. N. Singh et al., Drugs 29, 531-569 (1985) DOI PubMed; G. DeBono et al., Am. Heart J. 109, 1211-1223 (1985) DOI PubMed. Comprehensive description: R. T. Foster, R. A. Carr, Anal. Profiles Drug Subs. 19, 1-26 (1990).

Chemical structure

Properties

Crystals, mp 119-123°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 34381-68-5
M & B 17803A; IL-17803A; Acecor (SPA); Acetanol (RPR); Neptal (Procter & Gamble); Prent (Bayer); Sectral (RPR).
C18H28N2O4.HCl; mol wt 372.89.
C 57.98%, H 7.84%, N 7.51%, O 17.16%, Cl 9.51%.

Properties

Crystals from anhydr methanol-anhydr diethyl ether, mp 141-144°. Sol in alcohol, water. Very slightly sol in acetone, methylene chloride. Practically insol in ether. Soly at room temperature (mg/ml): water 200; ethanol 70.

Therapeutic Category

Antihypertensive; antianginal; antiarrhythmic (class II).

Keywords

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