6151. Metoprolol

Nomenclature

CAS number: 37350-58-6
1-[4-(2-Methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-2-propanol; (±)-1-(isopropylamino)-3-[p-(β-methoxyethyl)phenoxy]-2-propanol; CGP-2175; H-93/26.
C15H25NO3; mol wt 267.36.
C 67.38%, H 9.42%, N 5.24%, O 17.95%.

Description and references

β1-Adrenergic blocker lacking intrinsic sympathomimetic activity. Prepn: A. E. Brandstrom et al., DE 2106209; eidem, US 3998790 (1971, 1976 both to AB Hssle). Pharmacology: B. Ablad et al., Life Sci. 12, 107 (1973); Johansson, Eur. J. Pharmacol. 24, 194 (1973). Toxicology: N.-O. Bodin et al., Acta Pharmacol. Toxicol. 36, Suppl. V, 96 (1975). HPLC determn in dog plasma: J. Fang et al., J. Chromatogr. B 809, 9 (2004). Use in dogs with acquired cardiac disease: J. E. Rush et al., J. Vet. Cardiol. 4, 23 (2002). Clinical trials in acute myocardial infarction: L. Rydén et al., N. Engl. J. Med. 308, 614 (1983); Drugs 29, Suppl. 1, 2-8 (1985); in chronic heart failure: A. Hjalmarson et al., J. Am. Med. Assoc. 283, 1295 (2000). Comprehensive description: J. R. Luch, Anal. Profiles Drug Subs. 12, 325-356 (1983). Review of pharmacology, therapeutic efficacy: P. Benfield et al., Drugs 31, 376-429 (1986); of use in chronic heart failure: A. Prakash, A. Markham, ibid. 60, 647-678 (2000).

Chemical structure

Derivative

Succinate.

Nomenclature

CAS number: 98418-47-4
Selozok (AstraZeneca); Toprol-XL (AstraZeneca).
(C15H25NO3)2.C4H6O4; mol wt 652.82.
C 62.55%, H 8.65%, N 4.29%, O 24.51%.

Properties

White to off-white powder. Freely sol in water. Sol in methanol; sparingly sol in alcohol; slightly sol in isopropyl alcohol, dichloromethane. Practically insol in ethyl acetate, acetone, ether. heptane.

Derivative

Tartrate.

Nomenclature

CAS number: 56392-17-7
Beloc (AstraZeneca); Betaloc (AstraZeneca); Lopressor (Novartis); Lopresor (Novartis); Metropress (Ecosol); Prelis (Mibe); Seloken (AstraZeneca); Selopral (AstraZeneca).
(C15H25NO3)2.C4H6O6; mol wt 684.81.
C 59.63%, H 8.24%, N 4.09%, O 28.04%.

Properties

White, crystalline powder. Soly (mg/ml) at 25°: water >1000; methanol >500; chloroform 496; acetone 1.1; acetonitrile 0.89; hexane 0.001. Freely sol in methylene chloride, alcohol. Insol in ether. uv max (water): 223 nm (ε 23400). LD50 in female mice, male rats (mg/kg): 118, ≈90 i.v.; 2090, 3090 orally (Bodin).

Therapeutic Category

Antihypertensive; antianginal; antiarrhythmic (class II).

Therapeutic Category (Veterinary)

Antihypertensive; antianginal; antiarrhythmic (class II).

Keywords

β-Adrenergic Blocker; Antianginal; Antihypertensive; Aryloxypropanolamine Derivatives