Metaraminol

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Metaraminol
Clinical data
Trade namesAramine, Metaramin, Pressonex, others
Other namesMetaradrine; Hydroxynorephedrine; m-Hydroxypropadrine; m-Hydroxynorephedrine; meta-Hydroxynorephedrine; 3-Hydroxyphenylisopropanolamine; (1R,2S)-3,β-Dihydroxy-α-methylphenethylamine; (1R,2S)-3,β-Dihydroxyamphetamine
AHFS/Drugs.comInternational Drug Names
License data
Pregnancy
category
  • AU: C
Routes of
administration		Intramuscular injection, intravenous administration[1][2]
Drug classNorepinephrine releasing agent; Adrenergic receptor agonist; Sympathomimetic; Antihypotensive
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding45%[2]
MetabolismLiver[2]
Identifiers
  • (1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H13NO2
Molar mass167.208 g·mol−1
3D model (JSmol)
  • O[C@H](c1cc(O)ccc1)[C@@H](N)C
  • InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1 checkY
  • Key:WXFIGDLSSYIKKV-RCOVLWMOSA-N checkY
  (verify)

Metaraminol, also known as metaradrine and sold under the brand names Aramine and Pressonex among others, is a sympathomimetic medication which is used in the prevention and treatment of hypotension (low blood pressure), particularly as a complication of anesthesia.[1][4][5] It is given by intramuscular or intravenous administration.[1][2]

Side effects of metaraminol include reflex bradycardia among others. Metaraminol is a norepinephrine releasing agent and at high doses a α1-adrenergic receptor agonist with some β-adrenergic effect.[6][7][8] It is a substituted amphetamine and is closely related to phenylpropanolamine, ephedrine, and oxilofrine.[4][5]

Metaraminol was first described and introduced for medical use by 1955.[9][10]

Medical uses

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A commercially prepared pre-filled syringe of metaraminol for bolus use during anaesthesia, made up as 0.5 mg/mL (2.5 mg in 5 mL).

Metaraminol is given intravenously as either a bolus (often 0.5–1 mg doses) or as an infusion, usually via peripheral intravenous access. Metaraminol is commonly available as 10 mg in 1 mL, that requires dilution prior to administration (often made up to a 0.5 mg/mL solution), however pre-prepared syringes of metaraminol for bolus use for hypotension are also commonly available.[11][12]

Metaraminol is also used in the treatment of priapism.[13][14][15]

Pharmacology

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Pharmacodynamics

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The dominant mechanism of action for the vasopressor action of metaraminol is indirect,[6] with metaraminol displacing norepinephrine from neuronal vesicles in order for the noradrenaline to exert these effects.[7] Metaraminol at higher doses may have direct α-adrenergic agonist and β1-adrenergic agonist effects.[6][2] However at doses common in clinical practice, the indirect α1-adrenergic effects predominate, such that reflex bradycardia is a common side effect.

Chemistry

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Metaraminol, also known as (1R,2S)-3,β-dihydroxy-α-methylphenethylamine or as (1R,2S)-3,β-dihydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative.[4][5] It is the (1R,2S)-enantiomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine).[4][5] The drug is closely related to phenylpropanolamine ((1RS,2SR)-β-hydroxyamphetamine; norephedrine), ephedrine ((1R,2S)-β-hydroxy-N-methylamphetamine), para-hydroxynorephedrine (4,β-dihydroxyamphetamine), and oxilofrine (4,β-dihydroxy-N-methylamphetamine).[4][5]

The experimental log P of metaraminol is -0.27 and its predicted log P ranges from -0.59 to 0.07.[16][2][17]

Metaraminol is used pharmaceutically as the bitartrate salt.[4][5]

History

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Metaraminol was first described and introduced for medical use by 1955.[9][10][4]

Society and culture

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Names

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Metaraminol is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name, while its DCFTooltip Dénomination Commune Française is métaraminol and its DCITTooltip Denominazione Comune Italiana is metaraminolo.[4][5][18] As the bitartrate salt, its generic name is metaraminol bitartrate and this is its USANTooltip United States Adopted Name and JANTooltip Japanese Accepted Name, while metaraminol tartrate is its BANMTooltip British Approved Name.[4][5][18] A synonym of metaraminol is metaradrine.[5][18] Brand names of metaraminol include Aramin, Aramine, and Pressonex, among others.[4][5][18]

Availability

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Metaraminol appears to remain available in Argentina, Australia, Brazil, China, and Thailand.[18] It was previously marketed in many more countries, including the United States and United Kingdom, but seems to have been discontinued in these countries.[5] However, one formulation still remains available in the United States as of August 2024.[19]

References

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  1. ^ a b c https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/009509s026lbl.pdf
  2. ^ a b c d e f "Metaraminol: Uses, Interactions, Mechanism of Action". DrugBank Online. 1 July 2024. Retrieved 1 September 2024.
  3. ^ "Injection : Aramine (Metaraminol Bitartrate)" (PDF). U.S. Food and Drug Administration (FDA). Retrieved 12 March 2022.
  4. ^ a b c d e f g h i j Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 62. ISBN 978-1-4757-2085-3. Retrieved 31 August 2024.
  5. ^ a b c d e f g h i j k Schweizerischer Apotheker-Verein (2000). Index Nominum 2000: International Drug Directory. Index nominum. Medpharm Scientific Publishers. p. 660. ISBN 978-3-88763-075-1. Retrieved 31 August 2024.
  6. ^ a b c "Metaraminol". Deranged Physiology. Retrieved 19 October 2022.
  7. ^ a b Harrison DC, Chidsey CA, Braunwald E (September 1963). "Studies on the Mechanism of Action of Metaraminol (Aramine)". Annals of Internal Medicine. 59 (3): 297–305. doi:10.7326/0003-4819-59-3-297. PMID 14065947.
  8. ^ Kee VR (August 2003). "Hemodynamic pharmacology of intravenous vasopressors". Crit Care Nurse. 23 (4): 79–82. doi:10.4037/ccn2003.23.4.79. PMID 12961786.
  9. ^ a b Weil MH, Spink WW (June 1955). "Clinical studies on a vasopressor agent: metaraminol (aramine). I. Observations in normotensive subjects". Am J Med Sci. 229 (6): 661–669. doi:10.1097/00000441-195506000-00008. PMID 14376394.
  10. ^ a b Weil MH (October 1955). "Clinical studies on a vasopressor agent: metaraminol (aramine). II. Observations on its use in the management of shock". Am J Med Sci. 230 (4): 357–369. doi:10.1097/00000441-195510000-00001. PMID 13258566.
  11. ^ "Metaraminol 0.5 mg/ml, Solution for Injection in pre-filled syringe - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 19 October 2022.
  12. ^ Goodrick N, Wentrup T, Messer G, Gleeson P, Culwick M, Goulding G (21 August 2020). "Pre-filled emergency drugs: The introduction of pre-filled metaraminol and ephedrine syringes into the main operating theatres of a major metropolitan centre". Australasian Anaesthesia (2013): 127–134.
  13. ^ McDonald M, Santucci R (2004). "Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol". Int Braz J Urol. 30 (2): 121–122. doi:10.1590/S1677-55382004000200007. PMID 15703094.
  14. ^ Koga S, Shiraishi K, Saito Y (1990). "Post-traumatic priapism treated with metaraminol bitartrate: case report". J Trauma. 30 (12): 1591–3. doi:10.1097/00005373-199012000-00029. PMID 2258979.
  15. ^ Block T, Sturm W, Ernst G, Staehler G, Schmiedt E (1988). "[Metaraminol in therapy of various forms of priapism]". Urologe A. 27 (4): 225–9. PMID 3140463.
  16. ^ "Metaraminol". PubChem. Retrieved 1 September 2024.
  17. ^ "Metaraminol". ChemSpider. 1 September 2024. Retrieved 1 September 2024.
  18. ^ a b c d e https://web.archive.org/web/20160303210434/https://www.drugs.com/international/metaraminol.html
  19. ^ "Drugs@FDA: FDA-Approved Drugs". accessdata.fda.gov. Retrieved 1 September 2024.
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