Oxyfedrine

Oxyfedrine
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	C01DX03 (WHO) ;
Identifiers
	IUPAC name (RS)-3--1-(3-methoxyphenyl)propan-1-one;
CAS Number	15687-41-9 ;
PubChem CID	27454; 5489013;
ChemSpider	4590049;
UNII	DWL616XF1K;
KEGG	D08321 ;
CompTox Dashboard (EPA)	DTXSID0023408 ;
Chemical and physical data
Formula	C19H23NO3
Molar mass	313.397 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C((c1ccccc1)O)NCCC(=O)c2cccc(c2)OC;
	InChI InChI=1S/C19H23NO3/c1-14(19(22)15-7-4-3-5-8-15)20-12-11-18(21)16-9-6-10-17(13-16)23-2/h3-10,13-14,19-20,22H,11-12H2,1-2H3/t14-,19-/m0/s1; Key:GDYUVHBMFVMBAF-LIRRHRJNSA-N;
	(verify)

Oxyfedrine is a vasodilator and a β adrenoreceptor agonist. It 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 inotropic effects, thereby not precipitating angina pectoris. The latter property (positive chronotropic and inotropic effects) is particularly important, because other vasodilators used in angina may be counter productive causing coronary steal phenomenon.

Synergistic effects with antibiotics have been suggested.^[1]

Synthesis

Mannich condensation of PPA (1) with formaldehyde and m-acetanisole (3-Acetylanisole) (2) yields oxyfedrine (3).

References

^ Mazumdar K, Dutta NK, Kumar KA, Dastidar SG (April 2005). "In vitro and in vivo synergism between tetracycline and the cardiovascular agent oxyfedrine HCl against common bacterial strains". Biological & Pharmaceutical Bulletin. 28 (4): 713–7. doi:10.1248/bpb.28.713. PMID 15802815.
^ Thiele Kurt, U.S. patent 3,225,095 (1965 to Degussa).

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[pmid15802815-1] Mazumdar K, Dutta NK, Kumar KA, Dastidar SG (April 2005). "In vitro and in vivo synergism between tetracycline and the cardiovascular agent oxyfedrine HCl against common bacterial strains". Biological & Pharmaceutical Bulletin. 28 (4): 713–7. doi:10.1248/bpb.28.713. PMID 15802815.

[2] Thiele Kurt, U.S. patent 3,225,095 (1965 to Degussa).

[1]

[2]

v t e Vasodilators used in cardiac diseases (C01D)
Nitrovasodilators	Nitroglycerin # Isosorbide dinitrate # Isosorbide mononitrate Itramin tosilate Linsidomine Molsidomine Nicorandil Pentaerythritol tetranitrate Propatylnitrate Tenitramine Trolnitrate
Quinolone vasodilators	Flosequinan^‡
Others	Benziodarone Carbocromen Cinepazet Cloridarol Dilazep Efloxate Etafenone Gapicomine Heptaminol Hexobendine Imolamine Levosimendan Nesiritide Nicorandil Oxyfedrine Pimobendan Prenylamine Serelaxin Trapidil Vericiguat
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III