Chemistry:Oxyfedrine
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.[1][2][3][4][5][6] It is taken by mouth or intravenously.[1]
The drug acts as a β-adrenergic receptor partial agonist.[1][6] It may also act as a norepinephrine releasing agent via its major active metabolite norephedrine.[7] Oxyfedrine is a phenethylamine and amphetamine derivative.[5][6]
Oxyfedrine has been marketed in Europe, Hong Kong, India, Central America, and elsewhere.[3][8][9] It appears to remain marketed only in India.[9]
Pharmacology
Pharmacodynamics
Oxyfedrine is a β-adrenergic receptor partial agonist.[1][6] It appears to be non-selective for the β1- and β2-adrenergic receptors.[6] It is selective for the β-adrenergic receptors over the α-adrenergic receptors.[6] 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.[6] Norephedrine, a norepinephrine releasing agent, is a major active metabolite of oxyfedrine, and hence oxyfedrine may additionally act as an indirectly acting sympathomimetic.[7]
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,[1] 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.[additional citation(s) needed]
The drug is chemically and pharmacologically unrelated to any other antianginal drugs.[1]
Pharmacokinetics
Oxyfedrine's oral bioavailability is 85%.[1] The plasma protein binding is almost 100%.[1] Its elimination half-life is 4.2 hours.[1] Norephedrine is a major active metabolite of oxyfedrine.[7] The excretion of the active metabolites of oxyfedrine is 90% in urine.[1] About 75 to 100% of oxyfedrine is excreted as norephedrine.[7]
Chemistry
Oxyfedrine is a substituted phenethylamine and amphetamine derivative.[6] It is l-norephedrine with a bulky and lipophilic 3-methoxypropiophenone substituent at the nitrogen atom.[6]
Synthesis
Mannich condensation of phenylpropanolamine (1) with formaldehyde and m-acetanisole (3-acetylanisole) (2) yields oxyfedrine (3).[10]
Research
Synergistic effects of oxyfedrine with antibiotics against bacteria have been suggested.[11]
References
- ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 "Clinical pharmacokinetics of vasodilators. Part II". Clin Pharmacokinet 35 (1): 9–36. July 1998. doi:10.2165/00003088-199835010-00002. PMID 9673832.
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. 2014. p. 923. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA923. Retrieved 29 August 2024.
- ↑ 3.0 3.1 Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 777. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA777. Retrieved 29 August 2024.
- ↑ Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. 2012. p. 212. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA212. Retrieved 2024-08-29.
- ↑ 5.0 5.1 "Oxyfedrine: Uses, Interactions, Mechanism of Action". 23 June 2017. https://go.drugbank.com/drugs/DB13398.
- ↑ 6.0 6.1 6.2 6.3 6.4 6.5 6.6 6.7 6.8 "Oxyfedrine--a partial agonist at -adrenoceptors". Eur J Pharmacol 20 (2): 161–170. November 1972. doi:10.1016/0014-2999(72)90145-8. PMID 4405576.
- ↑ 7.0 7.1 7.2 7.3 "Excretion of norephedrine by man after oral administration of oxyfedrine". Eur J Clin Pharmacol 8 (3–4): 161–166. April 1975. doi:10.1007/BF00567109. PMID 1233214.
- ↑ "List of Vasodilators". https://www.drugs.com/international/oxyfedrine.html.
- ↑ 9.0 9.1 "List of Vasodilators". https://www.drugs.com/international/oxyfedrine.html.
- ↑ Thiele Kurt, U.S. Patent 3,225,095 (1965 to Degussa)
- ↑ "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. April 2005. doi:10.1248/bpb.28.713. PMID 15802815. https://www.jstage.jst.go.jp/article/bpb/28/4/28_4_713/_article.
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