Metipranolol
Title: Metipranolol
CAS Registry Number: 22664-55-7
CAS Name: 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-2,3,6-trimethylphenol 1-acetate
Additional Names: 1-(4-hydroxy-2,3,5-trimethylphenoxy)-3-(isopropylamino)-2-propanol 4-acetate; methypranol; trimepranol
Manufacturers' Codes: VUFB-6453
Trademarks: Betamet (Pharmaquest); Betanol (Dulcis); Disorat (Boehringer, Mann.); Glauline (Smith & Nephew); Glausyn (Novartis); Turoptin (Dispersa)
Molecular Formula: C17H27NO4
Molecular Weight: 309.40
Percent Composition: C 65.99%, H 8.80%, N 4.53%, O 20.68%
Literature References: b-Adrenergic blocker. Prepn: L. Blaha et al., CS 128471 (1968), C.A. 71, 3129a (1969). Pharmacology: W. Bartsch et al., Arzneim.-Forsch. 27, 1022 (1977). Plasma levels and pharmacodynamics in man: O. Mayer et al., Int. J. Clin. Pharmacol. Ther. Toxicol. 18, 113 (1980). Metabolic effects: R. P. Faupel, R. Gotzen, Med. Klin. 74, 929 (1979). Comparative effect in hypertension: K. Hayduk et al., Therapiewoche 29, 7528, 7530 (1979). Review of pharmacology and clinical trials in glaucoma and ocular hypertension: P. E. Battershill, E. M. Sorkin, Drugs 36, 601-615 (1988). Comprehensive description: J. Dohnal et al., Anal. Profiles Drug Subs. 19, 367-396 (1990).
Properties: Crystals from cyclohexane, mp 105-107° (Blaha), also reported as 108.5-110.5° (Florey). uv max (methanol): 278, 274 nm (A1%1cm 51.3 50.5). Freely sol in 95% ethanol, chloroform, benzene; slightly sol in ether. Practically insol in water. LD50 in mice (mg/kg): 31 i.v. (Bartsch).
Melting point: mp 105-107° (Blaha), also reported as 108.5-110.5° (Florey)
Absorption maximum: uv max (methanol): 278, 274 nm (A1%1cm 51.3 50.5)
Toxicity data: LD50 in mice (mg/kg): 31 i.v. (Bartsch)
 
Derivative Type: Hydrochloride
CAS Registry Number: 36592-77-5
Trademarks: Betamann (Mann); Optipranolol (Bausch & Lomb)
Molecular Formula: C17H27NO4.HCl
Molecular Weight: 345.86
Percent Composition: C 59.04%, H 8.16%, N 4.05%, O 18.50%, Cl 10.25%
Properties: Sol in water.
 
Therap-Cat: Antihypertensive; antiglaucoma agent.
Keywords: ?Adrenergic Blocker; Antiglaucoma; Antihypertensive; Aryloxypropanolamine Derivatives.

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