Oxyfedrine

Title: Oxyfedrine
CAS Registry Number: 15687-41-9
CAS Name: 3-[[(1S,2R)-2-Hydroxy-1-methyl-2-phenylethyl]amino]-1-(3-methoxyphenyl)-1-propanone
Additional Names: L-3-[(b-hydroxy-a-methylphenethyl)amino]-3¢-methoxypropiophenone; L-(1-hydroxy-1-phenyl-2-propylamino)-1-(m-methoxyphenyl)-1-propanone; oxyphedrine
Molecular Formula: C19H23NO3
Molecular Weight: 313.39
Percent Composition: C 72.82%, H 7.40%, N 4.47%, O 15.32%
Literature References: Partial b-adrenergic agonist with coronary vasodilating and positive inotropic effects. Prepn: K. Thiele, BE 630296; idem, US 3225095 (1963, 1965 both to Degussa). K. Thiele et al., Arzneim.-Forsch. 16, 1064 (1966). Absolute configuration determined by circular dichroism: J. Engel et al., Chem. Ztg. 105, 85 (1981). TLC determn: Musumarra, J. Chromatogr. 350, 151 (1985). Pharmacology: H. Hueller et al., Pharmazie 27, 242 (1972). Mode of action: P. Mentz, W. Forster, Arzneim.-Forsch. 34, 1739 (1984); N. Sternitzke, Z. Kardiol. 73, 586 (1984). In prevention of experimental myocardial necrosis in rats: S. D. Seth et al., Arzneim.-Forsch. 34, 678 (1984). Comparison with atenolol, q.v., in angina pectoris: L. Fananapazir, C. Bray, Br. J. Clin. Pharmacol. 20, 405 (1985).
Derivative Type: L-Form hydrochloride
CAS Registry Number: 16777-42-7
Manufacturers' Codes: D-563
Trademarks: Ildamen (Viatris); Modacor (Houd?
Molecular Formula: C19H23NO3.HCl
Molecular Weight: 349.85
Percent Composition: C 65.23%, H 6.91%, N 4.00%, O 13.72%, Cl 10.13%
Properties: Crystals from methanol, mp 192-194°. LD50 in mice (mg/kg): 29 i.v. (Hueller).
Melting point: mp 192-194°
Toxicity data: LD50 in mice (mg/kg): 29 i.v. (Hueller)
Derivative Type: DL-Form hydrochloride
CAS Registry Number: 16648-69-4
Properties: mp 173-175°. LD50 in mice (mg/kg): 34 i.v. (Hueller).
Melting point: mp 173-175°
Toxicity data: LD50 in mice (mg/kg): 34 i.v. (Hueller)
Therap-Cat: Antianginal. Treatment of coronary insufficiency.
Keywords: ?Adrenergic Agonist; Antianginal; Cardiotonic.
Oxyfluorfen Oxymetazoline Oxymethurea Oxypendyl Oxypertine

Oxyfedrine
Oxyfedrine2.png
Systematic (IUPAC) name
(RS)-3-[(2-Hydroxy-1-methyl-2-phenylethyl)amino]-1-(3-methoxyphenyl)propan-1-one
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 15687-41-9 YesY
ATC code C01DX03
PubChem CID 27454
UNII DWL616XF1K YesY
KEGG D08321 YesY
Chemical data
Formula C19H23NO3 
Mol. mass 313.39 g/mol
 YesY (what is this?)  (verify)

Oxyfedrine is a vasodilator. Oxyfedrine was found to depress the tonicity of coronary vessels, improve myocardial metabolism (so that heart can sustain hypoxia better) and also exert a positive chronotropic and inotrophic effects, thereby not precipitating angina pectoris. The latter property (positive chronotropic and inotrophic effects) is particularly important, because other vasodilators used in angina may be counter productive causing coronary steal phenomenon.

Synergestic effects with antibiotics have been suggested.[1]