Jump to content

Oxyfedrine

From Wikipedia, the free encyclopedia

Not to be confused with Oxilofrine.
Oxyfedrine
Clinical data
Trade namesIldamen, Modacor, Myofedrin
Other namesOxyfedrin; Oxyphedrine; Oxyphedrin; Oxifedrine; Oxifedrin; Oxiphedrine; Oxiphedrin
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, intravenous[1]
Drug classSympathomimetic; Coronary vasodilator; β-Adrenergic receptor partial agonist; Norepinephrine releasing agent
ATC code
Pharmacokinetic data
BioavailabilityOral: 85%[1]
Protein bindingAlmost 100%[1]
Metabolites• Norephedrine[2]
Elimination half-life4.2 hours[1]
ExcretionUrine (active metabolites 90%)[1]
Identifiers
  • (RS)-3-[(2-Hydroxy-1-methyl-2-phenylethyl)amino]-1-(3-methoxyphenyl)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H23NO3
Molar mass313.397 g·mol−1
3D model (JSmol)
  • C[C@@H]([C@@H](c1ccccc1)O)NCCC(=O)c2cccc(c2)OC
  • 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, 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

[edit]

Pharmacodynamics

[edit]

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.[additional citation(s) needed]

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

Pharmacokinetics

[edit]

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

[edit]

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

[edit]

Mannich condensation of phenylpropanolamine (1) with formaldehyde and m-acetanisole (3-acetylanisole) (2) yields oxyfedrine (3).[10]

Research

[edit]

Synergistic effects of oxyfedrine with antibiotics against bacteria have been suggested.[11]

References

[edit]
  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ a b Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 777. ISBN 978-3-88763-075-1. Retrieved 29 August 2024.
  5. ^ 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.
  6. ^ a b "Oxyfedrine: Uses, Interactions, Mechanism of Action". DrugBank Online. 23 June 2017. Retrieved 29 August 2024.
  7. ^ 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.
  8. ^ https://web.archive.org/web/20121020185501/https://www.drugs.com/international/oxyfedrine.html
  9. ^ a b https://web.archive.org/web/20210106003945/https://www.drugs.com/international/oxyfedrine.html
  10. ^ Thiele Kurt, U.S. patent 3,225,095 (1965 to Degussa)
  11. ^ 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.


Retrieved from "https://en.wikipedia.org/w/index.php?title=Oxyfedrine&oldid=1253136757"