Oxyfedrine

Overview

Oxyfedrine, sold under the brand names Ildamen and Myofedrin among others, is a sympathomimetic agent and coronary vasodilator which is used in the treatment of coronary heart disease, angina pectoris, and acute myocardial infarction. It is taken by mouth or intravenously.[1–6] WP

The drug acts as a β-adrenergic receptor partial agonist. It may also act as a norepinephrine releasing agent via its major active metabolite norephedrine. Oxyfedrine is a phenethylamine and amphetamine derivative.[1][5][6][7] WP

Oxyfedrine has been marketed in Europe, Hong Kong, India, Central America, and elsewhere. It appears to remain marketed only in India.[3][8] WP

Pharmacology

Pharmacodynamics

Oxyfedrine is a β-adrenergic receptor partial agonist. It appears to be non-selective for the β₁- and β₂-adrenergic receptors. It is selective for the β-adrenergic receptors over the α-adrenergic receptors. However, it has also been reported to interact with the α-adrenergic receptors at high concentrations, acting as a partial agonist or antagonist of these receptors. Norephedrine, a norepinephrine releasing agent, is a major active metabolite of oxyfedrine, and hence oxyfedrine may additionally act as an indirectly acting sympathomimetic.[1][6][7] WP

It has been 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.[1] WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.

The drug is chemically and pharmacologically unrelated to any other antianginal drugs.[1] WP

Pharmacokinetics

Oxyfedrine's oral bioavailability is 85%. The plasma protein binding is almost 100%. Its elimination half-life is 4.2 hours. Norephedrine is a major active metabolite of oxyfedrine. The excretion of the active metabolites of oxyfedrine is 90% in urine. About 75 to 100% of oxyfedrine is excreted as norephedrine.[1][7] WP

Research

Research

Synergistic effects of oxyfedrine with antibiotics against bacteria have been suggested.[9] WP

Chemistry

Formula

C19H23NO3 PC

CAS number

15687-41-9 PC

Molar mass (g/mol)

313.4 PC

IUPAC name (computed by PubChem)

3-[[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-(3-methoxyphenyl)propan-1-one PC

SMILES

C[C@@H]([C@@H](C1=CC=CC=C1)O)NCCC(=O)C2=CC(=CC=C2)OC PC

InChIKey

GDYUVHBMFVMBAF-LIRRHRJNSA-N PC

PubChem CID

5489013

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Kirsten R, Nelson K, Kirsten D, Heintz B. Clinical pharmacokinetics of vasodilators. Part II. Clin Pharmacokinet. July 1998. doi:10.2165/00003088-199835010-00002 · PMID 9673832
2. Other Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 2014
3. Other Schweizerischer Apotheker-Verein. Index Nominum 2000: International Drug Directory. 2000
4. Other Morton IK, Hall JM. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 2012
5. Harm reduction site Oxyfedrine: Uses, Interactions, Mechanism of Action. 23 June 2017
6. Journal / agency Beckett PR, Foster RW. Oxyfedrine--a partial agonist at -adrenoceptors. Eur J Pharmacol. November 1972. doi:10.1016/0014-2999(72)90145-8 · PMID 4405576
7. Journal / agency Appel E, Planz G, Palm D, Grobecker H, Stratmann D, Donike M. Excretion of norephedrine by man after oral administration of oxyfedrine. Eur J Clin Pharmacol. April 1975. doi:10.1007/BF00567109 · PMID 1233214
8. Other List of Vasodilators
9. Journal / agency Mazumdar K, Dutta NK, Kumar KA, Dastidar SG. In vitro and in vivo synergism between tetracycline and the cardiovascular agent oxyfedrine HCl against common bacterial strains. Biological & Pharmaceutical Bulletin. April 2005. doi:10.1248/bpb.28.713 · PMID 15802815

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.