oxyfedrine
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Distinguish|Oxilofrine}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 444397365
| IUPAC_name = (RS)-3-[(2-Hydroxy-1-methyl-2-phenylethyl)amino]-1-(3-methoxyphenyl)propan-1-one
| image = Oxyfedrine.svg
| width = 275px
| tradename = Ildamen, Modacor, Myofedrin
| Drugs.com = {{drugs.com|international|oxyfedrine}}
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = Oral, intravenous
| class = Sympathomimetic; Coronary vasodilator; β-Adrenergic receptor partial agonist; Norepinephrine releasing agent
| bioavailability = Oral: 85%
| metabolism =
| metabolites = • Norephedrine
| elimination_half-life = 4.2{{nbsp}}hours
| excretion = Urine (active metabolites 90%)
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 15687-41-9
| ATC_prefix = C01
| ATC_suffix = DX03
| DrugBank =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DWL616XF1K
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08321
| PubChem = 5489013
| ChemSpiderID = 4590049
| ChEBI =
| ChEMBL = 1651913
| synonyms = Oxyfedrin; Oxyphedrine; Oxyphedrin; Oxifedrine; Oxifedrin; Oxiphedrine; Oxiphedrin
| C=19 | H=23 | N=1 | O=3
| SMILES = C[C@@H]([C@@H](c1ccccc1)O)NCCC(=O)c2cccc(c2)OC
| StdInChI = 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
| StdInChIKey = GDYUVHBMFVMBAF-LIRRHRJNSA-N
}}
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.{{cite journal | vauthors = Kirsten R, Nelson K, Kirsten D, Heintz B | title = Clinical pharmacokinetics of vasodilators. Part II | journal = Clin Pharmacokinet | volume = 35 | issue = 1 | pages = 9–36 | date = July 1998 | pmid = 9673832 | doi = 10.2165/00003088-199835010-00002 | url = }}{{cite book | vauthors = Elks J | title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies | publisher=Springer US | year=2014 | isbn=978-1-4757-2085-3 | url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA923 | access-date=29 August 2024 | page=923}}{{cite book | author=Schweizerischer Apotheker-Verein | title=Index Nominum 2000: International Drug Directory | publisher=Medpharm Scientific Publishers | year=2000 | isbn=978-3-88763-075-1 | url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA777 | access-date=29 August 2024 | page=777}}{{cite book | vauthors = Morton IK, Hall JM | title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms | publisher=Springer Netherlands | year=2012 | isbn=978-94-011-4439-1 | url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA212 | access-date=2024-08-29 | page=212}}{{cite web | title=Oxyfedrine: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=23 June 2017 | url=https://go.drugbank.com/drugs/DB13398 | access-date=29 August 2024}} It is taken by mouth or intravenously.
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.
Oxyfedrine has been marketed in Europe, Hong Kong, India, Central America, and elsewhere.{{cite web | url=https://www.drugs.com/international/oxyfedrine.html | archive-url=https://web.archive.org/web/20121020185501/https://www.drugs.com/international/oxyfedrine.html | archive-date=20 October 2012 | title=List of Vasodilators }}{{cite web | url=https://www.drugs.com/international/oxyfedrine.html | archive-url=https://web.archive.org/web/20210106003945/https://www.drugs.com/international/oxyfedrine.html | archive-date=6 January 2021 | title=List of Vasodilators }} It appears to remain marketed only in India.
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.
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.{{Additional citation needed|date=August 2024}}
The drug is chemically and pharmacologically unrelated to any other antianginal drugs.
=Pharmacokinetics=
Oxyfedrine's oral bioavailability is 85%. The plasma protein binding is almost 100%. Its elimination half-life is 4.2{{nbsp}}hours. Norephedrine is a major active metabolite of oxyfedrine.{{cite journal | vauthors = Appel E, Planz G, Palm D, Grobecker H, Stratmann D, Donike M | title = Excretion of norephedrine by man after oral administration of oxyfedrine | journal = Eur J Clin Pharmacol | volume = 8 | issue = 3–4 | pages = 161–166 | date = April 1975 | pmid = 1233214 | doi = 10.1007/BF00567109 | url = }} The excretion of the active metabolites of oxyfedrine is 90% in urine. About 75 to 100% of oxyfedrine is excreted as norephedrine.
Chemistry
Oxyfedrine is a substituted phenethylamine and amphetamine derivative.{{cite journal | vauthors = Beckett PR, Foster RW | title = Oxyfedrine--a partial agonist at -adrenoceptors | journal = Eur J Pharmacol | volume = 20 | issue = 2 | pages = 161–170 | date = November 1972 | pmid = 4405576 | doi = 10.1016/0014-2999(72)90145-8 | url = }} It is l-norephedrine with a bulky and lipophilic 3-methoxypropiophenone substituent at the nitrogen atom.
=Synthesis=
Mannich condensation of phenylpropanolamine (1) with formaldehyde and m-acetanisole (3-acetylanisole) (2) yields oxyfedrine (3).Thiele Kurt, {{US patent|3225095}} (1965 to Degussa)
Research
Synergistic effects of oxyfedrine with antibiotics against bacteria have been suggested.{{cite journal | vauthors = Mazumdar K, Dutta NK, Kumar KA, Dastidar SG | title = In vitro and in vivo synergism between tetracycline and the cardiovascular agent oxyfedrine HCl against common bacterial strains | journal = Biological & Pharmaceutical Bulletin | volume = 28 | issue = 4 | pages = 713–7 | date = April 2005 | pmid = 15802815 | doi = 10.1248/bpb.28.713 | url = https://www.jstage.jst.go.jp/article/bpb/28/4/28_4_713/_article | doi-access = free }}
References
{{Reflist}}
{{Vasodilators used in cardiac diseases}}
{{Adrenergic receptor modulators}}
{{Monoamine releasing agents}}
Category:Beta-adrenergic agonists
Category:Beta-Hydroxyamphetamines
Category:Drugs acting on the cardiovascular system
Category:Norepinephrine releasing agents