Chemistry:Metaraminol

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Short description: Antihypotensive medication
Metaraminol
Metaraminol Structural Formulae.png
Clinical data
Trade namesAramine, Metaramin, Pressonex
AHFS/Drugs.comInternational Drug Names
License data
Pregnancy
category
  • AU: C
Routes of
administration
Intravenous, endotracheal
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a
Protein binding~45%
MetabolismLiver
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC9H13NO2
Molar mass167.208 g·mol−1
3D model (JSmol)
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Metaraminol, previously sold under the brand name Aramine among others and also known as metaradrine, is a stereoisomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine), is a potent sympathomimetic amine used in the prevention and treatment of hypotension, particularly as a complication of anesthesia. It is an α1-adrenergic receptor agonist with some β-adrenergic effect.[2] It is currently sold in its generic form by Slayback Pharma.[3]

Pharmacology and use as a vasopressor

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.[4][5]

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).

Pharmacodynamics

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

Research

Metaraminol is also used in the treatment of priapism.[8][9][10]

References

  1. "Injection : Aramine (Metaraminol Bitartrate)". https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/009509s026lbl.pdf. 
  2. "Hemodynamic pharmacology of intravenous vasopressors". Crit Care Nurse 23 (4): 79–82. Aug 2003. doi:10.4037/ccn2003.23.4.79. PMID 12961786. http://ccn.aacnjournals.org/content/23/4/79.long. 
  3. "ANDA Approval for Metaraminol". United States Food and Drug Administration. 24 August 2021. https://www.accessdata.fda.gov/drugsatfda_docs/appletter/2021/211304Orig1s000ltr.pdf. 
  4. "Metaraminol 0.5 mg/ml, Solution for Injection in pre-filled syringe - Summary of Product Characteristics (SmPC) - (emc)". https://www.medicines.org.uk/emc/product/11698/smpc. 
  5. "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. 21 August 2020. https://search.informit.org/doi/abs/10.3316/INFORMIT.477021141406775. 
  6. 6.0 6.1 "Metaraminol" (in en). Deranged Physiology. https://derangedphysiology.com/main/cicm-primary-exam/required-reading/cardiovascular-system/Chapter%20979/metaraminol. 
  7. "Studies on the Mechanism of Action of Metaraminol (Aramine)". Annals of Internal Medicine 59 (3): 297–305. September 1963. doi:10.7326/0003-4819-59-3-297. PMID 14065947. 
  8. "Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol.". Int Braz J Urol 30 (2): 121–2. 2004. doi:10.1590/S1677-55382004000200007. PMID 15703094. 
  9. "Post-traumatic priapism treated with metaraminol bitartrate: case report.". J Trauma 30 (12): 1591–3. 1990. doi:10.1097/00005373-199012000-00029. PMID 2258979. 
  10. "[Metaraminol in therapy of various forms of priapism]". Urologe A 27 (4): 225–9. 1988. PMID 3140463. 

External links