Oxyfedrine
| Clinical data | |
|---|---|
| Trade names | Ildamen, Modacor, Myofedrin |
| Other names | Oxyfedrin; Oxyphedrine; Oxyphedrin; Oxifedrine; Oxifedrin; Oxiphedrine; Oxiphedrin |
| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Oral, intravenous[1] |
| Drug class | Sympathomimetic; Coronary vasodilator; β-Adrenergic receptor partial agonist; Norepinephrine releasing agent |
| ATC code | |
| Pharmacokinetic data | |
| Bioavailability | Oral: 85%[1] |
| Protein binding | Almost 100%[1] |
| Metabolites | • Norephedrine[2] |
| Elimination half-life | 4.2 hours[1] |
| Excretion | Urine (active metabolites 90%)[1] |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
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| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C19H23NO3 |
| Molar mass | 313.397 g·mol−1 |
| 3D model (JSmol) | |
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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][3][4][5][6][7] It is taken by mouth or intravenously.[1]
The drug acts as a β-adrenergic receptor partial agonist.[1][7] It may also act as a norepinephrine releasing agent via its major active metabolite norephedrine.[2] Oxyfedrine is a phenethylamine and amphetamine derivative.[6][7]
Oxyfedrine has been marketed in Europe, Hong Kong, India, Central America, and elsewhere.[4][8][9] It appears to remain marketed only in India.[9]
Pharmacology
Pharmacodynamics
Oxyfedrine is a β-adrenergic receptor partial agonist.[1][7] It appears to be non-selective for the β1- and β2-adrenergic receptors.[7] It is selective for the β-adrenergic receptors over the α-adrenergic receptors.[7] 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.[7] Norephedrine, a norepinephrine releasing agent, is a major active metabolite of oxyfedrine, and hence oxyfedrine may additionally act as an indirectly acting sympathomimetic.[2]
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.
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.[2] The excretion of the active metabolites of oxyfedrine is 90% in urine.[1] About 75 to 100% of oxyfedrine is excreted as norephedrine.[2]
Chemistry
Oxyfedrine is a substituted phenethylamine and amphetamine derivative.[7] It is l-norephedrine with a bulky and lipophilic 3-methoxypropiophenone substituent at the nitrogen atom.[7]
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
- ^ a b c d e f g h i j k l m n o Kirsten R, Nelson K, Kirsten D, Heintz B (July 1998). "Clinical pharmacokinetics of vasodilators. Part II". Clin Pharmacokinet. 35 (1): 9–36. doi:10.2165/00003088-199835010-00002. PMID 9673832.
- ^ a b c d e Appel E, Planz G, Palm D, Grobecker H, Stratmann D, Donike M (April 1975). "Excretion of norephedrine by man after oral administration of oxyfedrine". Eur J Clin Pharmacol. 8 (3–4): 161–166. doi:10.1007/BF00567109. PMID 1233214.
- ^ Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 923. ISBN 978-1-4757-2085-3. Retrieved 29 August 2024.
- ^ a b Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Medpharm Scientific Publishers. p. 777. ISBN 978-3-88763-075-1. Retrieved 29 August 2024.
- ^ Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Netherlands. p. 212. ISBN 978-94-011-4439-1. Retrieved 2024-08-29.
- ^ a b "Oxyfedrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 23 June 2017. Retrieved 29 August 2024.
- ^ a b c d e f g h i Beckett PR, Foster RW (November 1972). "Oxyfedrine--a partial agonist at -adrenoceptors". Eur J Pharmacol. 20 (2): 161–170. doi:10.1016/0014-2999(72)90145-8. PMID 4405576.
- ^ "List of Vasodilators". Archived from the original on 20 October 2012.
- ^ a b "List of Vasodilators". Archived from the original on 6 January 2021.
- ^ Thiele Kurt, U.S. patent 3,225,095 (1965 to Degussa)
- ^ 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.