Penbutolol
Title: Penbutolol
CAS Registry Number: 38363-40-5
CAS Name: (2S)-1-(2-Cyclopentylphenoxy)-3-[(1,1-dimethylethyl)amino]-2-propanol
Additional Names: (S)-1-(tert-butylamino)-3-(o-cyclopentylphenoxy)-2-propanol; (-)-1-tert-butylamino-2-hydroxy-3-(2¢-cyclopentylphenoxy)propane
Molecular Formula: C18H29NO2
Molecular Weight: 291.43
Percent Composition: C 74.18%, H 10.03%, N 4.81%, O 10.98%
Literature References: b-Adrenergic blocker. Prepn: H. Ruschig et al., ZA 6807915; eidem, US 3551493 (1969, 1970 both to Hoechst). Preliminary chemistry and pharmacology: G. Härtfelder et al., Arzneim.-Forsch. 22, 930 (1972). Physicochemical and analytical study: P. Hajdu, D. Damm, ibid. 29, 602 (1979). Pharmacology: J. Kaiser et al., ibid. 30, 420 (1980). Action specificity: J. Kaiser ibid. 427. Crystallographic study: J. M. Leger et al., Mol. Pharmacol. 17, 339 (1980). Hemodynamic effects: P. Lund-Johansen, Eur. J. Clin. Pharmacol. 16, 149 (1979). Clinical study in hypertension: J. L. Cangiano et al., J. Clin. Pharmacol. 19, 384 (1979). HPLC determn in plasma: R. K. Bhamra et al., Biomed. Chromatogr. 1, 140 (1986). Review of pharmacology and therapeutic efficacy: R. C. Heel et al., Drugs 22, 1-25 (1981).
Properties: Crystals, mp 68-72°. [a]20D -11.5° (c = 1 in methanol). pKa 9.3 (1.5 mmol/l in 25% ethanol). Sol in methanol, ethanol, chloroform.
Melting point: mp 68-72°
pKa: pKa 9.3 (1.5 mmol/l in 25% ethanol)
Optical Rotation: [a]20D -11.5° (c = 1 in methanol)
 
Derivative Type: Sulfate
CAS Registry Number: 38363-32-5
Manufacturers' Codes: HOE-893d; HOE-39-893d
Trademarks: Betapressin (HMR); Levatol (Schwarz); Paginol (Jugoremedija)
Molecular Formula: (C18H29NO2)2.H2SO4
Molecular Weight: 680.94
Percent Composition: C 63.50%, H 8.88%, N 4.11%, O 18.80%, S 4.71%
Properties: Crystals, mp 216-218° (dec). [a]20D -24.6° (c = 1 in methanol).
Melting point: mp 216-218° (dec)
Optical Rotation: [a]20D -24.6° (c = 1 in methanol)
 
Therap-Cat: Antihypertensive; antianginal; antiarrhythmic.
Keywords: ?Adrenergic Blocker; Antianginal; Antiarrhythmic; Antihypertensive; Aryloxypropanolamine Derivatives.

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