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Metaraminol
Clinical data
Trade names	Aramine, Metaramin, Pressonex, others
Other names	Metaradrine; Hydroxynorephedrine; m-Hydroxypropadrine; m-Hydroxynorephedrine; meta-Hydroxynorephedrine; 3-Hydroxyphenylisopropanolamine; (1R,2S)-3,β-Dihydroxy-α-methylphenethylamine; (1R,2S)-3,β-Dihydroxyamphetamine
AHFS/Drugs.com	International Drug Names
License data	US DailyMed: Metaraminol;
Pregnancy; category	AU: C; ;
Routes of; administration	Intramuscular injection, intravenous administration
Drug class	Norepinephrine releasing agent; Adrenergic receptor agonist; Sympathomimetic; Antihypotensive
ATC code	C01CA09 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Protein binding	45%
Metabolism	Liver
Identifiers
	IUPAC name (1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol;
CAS Number	54-49-9 ; 33402-03-8 (bitartrate);
PubChem CID	5906;
IUPHAR/BPS	7229;
DrugBank	DB00610 ;
ChemSpider	5695 ;
UNII	818U2PZ2EH;
KEGG	D08192 ;
ChEBI	CHEBI:6794 ;
ChEMBL	ChEMBL1201319 ;
CompTox Dashboard (EPA)	DTXSID8023268 ;
Chemical and physical data
Formula	C9H13NO2
Molar mass	167.208 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@H](c1cc(O)ccc1)[C@@H](N)C;
	InChI 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 ; Key:WXFIGDLSSYIKKV-RCOVLWMOSA-N ;
	(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

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

Pharmacodynamics

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

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

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

Society and culture

Names

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

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

^ ^a ^b ^c https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/009509s026lbl.pdf
^ ^a ^b ^c ^d ^e ^f "Metaraminol: Uses, Interactions, Mechanism of Action". DrugBank Online. 1 July 2024. Retrieved 1 September 2024.
^ "Injection : Aramine (Metaraminol Bitartrate)" (PDF). U.S. Food and Drug Administration (FDA). Retrieved 12 March 2022.
^ ^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.
^ ^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.
^ ^a ^b ^c "Metaraminol". Deranged Physiology. Retrieved 19 October 2022.
^ ^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.
^ 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.
^ ^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.
^ ^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.
^ "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.
^ 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.
^ 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.
^ 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.
^ 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.
^ "Metaraminol". PubChem. Retrieved 1 September 2024.
^ "Metaraminol". ChemSpider. 1 September 2024. Retrieved 1 September 2024.
^ ^a ^b ^c ^d ^e https://web.archive.org/web/20160303210434/https://www.drugs.com/international/metaraminol.html
^ "Drugs@FDA: FDA-Approved Drugs". accessdata.fda.gov. Retrieved 1 September 2024.

External links

"Metaraminol". Drug Information Portal. U.S. National Library of Medicine.
"Metaraminol bitartrate". Drug Information Portal. U.S. National Library of Medicine.

[Aaramine-Label-1] ttps://www.accessdata.fda.gov/drugsatfda_docs/label/2001/009509s026lbl.pdf

[DrugBank-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.

[Elks2014-4] ^ ^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.

[IndexNominum2000-5] ^ ^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.

[:0-6] "Metaraminol". Deranged Physiology. Retrieved 19 October 2022.

[pmid14065947-7] 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.

[WeilSpink1955-9] 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.

[Weil1955-10] 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.

[McDonaldSantucci2004-13] 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.

[KogaShiraishiSaito1990-14] 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.

[Block-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.

[PubChem-16] "Metaraminol". PubChem. Retrieved 1 September 2024.

[ChemSpider-17] "Metaraminol". ChemSpider. 1 September 2024. Retrieved 1 September 2024.

[Drugs.com-International-18] ttps://web.archive.org/web/20160303210434/https://www.drugs.com/international/metaraminol.html

[Drugs@FDA-19] "Drugs@FDA: FDA-Approved Drugs". accessdata.fda.gov. Retrieved 1 September 2024.

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PROFILPELAJAR.COM

Metaraminol

Medical uses

Pharmacology

Pharmacodynamics

Chemistry

History

Society and culture

Names

Availability

References

External links

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