Acebutolol

Title: Acebutolol
CAS Registry Number: 37517-30-9
CAS Name: N-[3-Acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide
Additional Names: 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
Molecular Formula: C18H28N2O4
Molecular Weight: 336.43
Percent Composition: C 64.26%, H 8.39%, N 8.33%, O 19.02%
Literature References: Cardioselective b-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); Basil et al., ibid. 48, 198 (1973); Lewis et al., Br. Heart J. 35, 743 (1973). HPLC determn in plasma and urine: M. Piquette-Miller et al., J. Chromatogr. 526, 129 (1990). 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); G. DeBono et al., Am. Heart J. 109, 1211-1223 (1985). Comprehensive description: R. T. Foster, R. A. Carr, Anal. Profiles Drug Subs. 19, 1-26 (1990).
Properties: Crystals, mp 119-123°.
Melting point: mp 119-123°
Derivative Type: Hydrochloride
CAS Registry Number: 34381-68-5
Manufacturers' Codes: M & B 17803A; IL-17803A
Trademarks: Acecor (SPA); Acetanol (RPR); Neptal (Procter & Gamble); Prent (Bayer); Sectral (RPR)
Molecular Formula: C18H28N2O4.HCl
Molecular Weight: 372.89
Percent Composition: C 57.98%, H 7.84%, N 7.51%, O 17.16%, Cl 9.51%
Properties: Crystals from anhydr methanol-anhydr diethyl ether, mp 141-143°. Freely sol in water. Soly at room temperature (mg/ml): water 200; ethanol 70.
Melting point: mp 141-143°
Therap-Cat: Antihypertensive; antianginal; antiarrhythmic (class II).
Keywords: ?Adrenergic Blocker; Antianginal; Antiarrhythmic; Antihypertensive; Aryloxypropanolamine Derivatives.
Acecainide Acecarbromal Aceclofenac Acedapsone Acediasulfone

Acebutolol
Acebutolol structure.svg
Acebutolol ball-and-stick.png
Systematic (IUPAC) name
(RS)-N-{3-acetyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}butanamide
Clinical data
Trade names Sectral
AHFS/Drugs.com monograph
MedlinePlus a687003
Licence data US FDA:link
Pregnancy cat. C (AU) B (US)
Legal status Prescription only
Routes oral, iv
Pharmacokinetic data
Bioavailability 40% (range 35 to 50%)
Metabolism Hepatic
Half-life 3-4 hours (parent drug)
8-13 hours (active metabolite)
Excretion Renal: 30%
Biliary: 60%
Identifiers
CAS number 37517-30-9 YesY
ATC code C07AB04
PubChem CID 1978
DrugBank DB01193
ChemSpider 1901 YesY
UNII 67P356D8GH YesY
KEGG D02338 YesY
ChEBI CHEBI:2379 YesY
ChEMBL CHEMBL642 YesY
Chemical data
Formula C18H28N2O4 
Mol. mass 336.426 g/mol
Physical data
Melt. point 121 °C (250 °F)
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Acebutolol (trade names Sectral, Prent) is a beta blocker for the treatment of hypertension and arrhythmias.