metaraminol

Trade name: aramine

Small moleculeapproved

Approved

Sep 29, 1954

Metaraminol is a potent sympathomimetic amine that increases both systolic and diastolic blood pressure, is an adrenergic receptor alpha-1 agonist.. Metaraminol is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor. Metaraminol is also used in the treatment of priapism, in spite of this application was not approved, it appears to be effective. — NCATS

Clinical trial activity

5 trials · 4 clinical orgs · 7 marketing orgs

Phase 1

Phase 2

Phase 3

Phase 4

Earliest trial started Nov 1, 2009 (NCT01108874)

Timeline

1950s

Sep 29, 1954
Merck — Earliest FDA Approval
Sep 29, 1954
Merck — NDA Secondary Org
Sep 29, 1954
Merck — NDA Organization

1970s

Apr 17, 1972
Fresenius — Marketing Organization
Sep 22, 1972
Abraxis — Marketing Organization

2000s

Jan 1, 2009
Earliest Phase 2 Sponsor(trial)

2010s

Jan 1, 2011
Earliest Phase 3 Sponsor(trial)

2020s

Aug 24, 2021
Azurity — Marketing Organization
Aug 24, 2021
Slayback Pharma Llc — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Adrenergic receptor alpha-1AGONIST
Adrenergic receptor alpha-1 agonist

Approval history

approvedPriority reviewSep 29, 1954

Chemistry & pharmacology

Loading structure…

SMILES

C[C@H](N)[C@H](O)c1cccc(O)c1

Mol. weight: 167.21 g/mol
Lipinski Ro5: Pass
Rule of 3: No
Chirality: Single Stereoisomer
Inorganic: No
Polymer: No
Delivery: Parenteral
Availability: Prescription Only

Oral

Parenteral

Yes

Topical

Sources

Also known as

1-metaraminol
1-metaraminol
1-(m-hydroxyphenyl)-2-amino-1-propanol
1-(m-hydroxyphenyl)-2-amino-1-propanol
2-amino-1-(m-hydroxyphenyl)-1-propanol
2-amino-1-(m-hydroxyphenyl)-1-propanol
3-hydroxyphenylisopropanolamine
3-hydroxyphenylisopropanolamine
alpha-(1-aminoethyl)-3-hydroxybenzenemethanol
alpha-(1-aminoethyl)-3-hydroxybenzenemethanol
alpha-(m-hydroxyphenyl)-beta-aminopropanol
alpha-(m-hydroxyphenyl)-beta-aminopropanol
aramine
aramine
aramine
(-)-erythro-metaraminol
(-)-erythro-metaraminol
(-)-erythro-metaraminol
hydroxynorephedrine
hydroxynorephedrine
hydroxyphenylpropanolamine
l-metaraminol
l-metaraminol
l-metaraminol
metaradrine
metaradrine bitartrate
metaradrine bitartrate
metaraminol
metaraminol
metaraminol
metaraminol
metaraminol
metaraminol
metaraminol
(-)-metaraminol
métaraminol
métaraminol
metaraminol bitartrate
metaraminol bitartrate
metaraminol bitartrate
metaraminol bitartrate
metaraminol bitartrate
metaraminol bitartrate
metaraminol bitartrate
metaraminolum
metaraminolum
(-)-m-hydroxynorephedrine
m-hydroxynorephedrine
m-hydroxy norephedrine
m-hydroxy norephedrine
m-hydroxyphenylpropanolamine
m-hydroxyphenylpropanolamine
m-hydroxyphenylpropanolamine
m-hydroxypropadrine
m-hydroxypropadrine

Clinical trials

NCT ID	Phase	Start date	Sponsor(s)
NCT05084599	Phase 4	Jan 1, 2022	Peking University
NCT04991662	Phase 4	Oct 10, 2021	Peking University, Xuzhou Medical University
NCT02245191	N/A	Jul 1, 2014	University of Sao Paulo
NCT01451060	Phase 3	Jun 1, 2011	Instituto de Medicina Integral Professor Fernando Figueira
NCT01108874	Phase 2	Nov 1, 2009	University of Sao Paulo

Showing 5 of 5 trials

Page 1 / 1

Organizations

Research & Development (4)

Organization	Org type	Trials	As lead sponsor	Phases	Earliest year
Peking University	Academic/Hospital	2	1	1	2021
University of Sao Paulo	Academic/Hospital	2	2	2	2009
Instituto de Medicina Integral Professor Fernando Figueira	Academic/Hospital	1	1	1	2011
Xuzhou Medical University	Academic/Hospital	1	1	1	2021

4 organizations

Page 1 / 1

Marketing (8)

Organization	Org type	Relationship	Date
Abraxis	For profit	MKTG	Sep 22, 1972
Azurity	For profit	MKTG	Aug 24, 2021
Elkins Sinn	For profit	MKTG	—
Fresenius	For profit	MKTG	Apr 17, 1972
G D Searle	For profit	MKTG	—
Merck	For profit	NDA2	Sep 29, 1954
Merck	For profit	NDA	Sep 29, 1954
Slayback Pharma Llc	For profit	MKTG	Aug 24, 2021