U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO2
Molecular Weight 167.2054
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METARAMINOL

SMILES

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

InChI

InChIKey=WXFIGDLSSYIKKV-RCOVLWMOSA-N
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

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
METARAMINOL BITARTRATE

Approved Use

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.
Palliative
METARAMINOL BITARTRATE

Approved Use

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.
Palliative
METARAMINOL BITARTRATE

Approved Use

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.
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
10 mg 4 times / hour single, intravenous
Dose: 10 mg, 4 times / hour
Route: intravenous
Route: single
Dose: 10 mg, 4 times / hour
Sources:
unhealthy, 38 years
n = 1
Health Status: unhealthy
Age Group: 38 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Bigeminal rhythm...
AEs leading to
discontinuation/dose reduction:
Bigeminal rhythm (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Bigeminal rhythm 1 patient
Disc. AE
10 mg 4 times / hour single, intravenous
Dose: 10 mg, 4 times / hour
Route: intravenous
Route: single
Dose: 10 mg, 4 times / hour
Sources:
unhealthy, 38 years
n = 1
Health Status: unhealthy
Age Group: 38 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >1000 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
SHOCK CAUSED BY CONTINUOUS INFUSION OF METARAMINOL BITARTRATE (ARAMINE).
1964 Feb 1
Augmented natriuretic response to infusion of saline in dogs rendered acutely hypertensive with metaraminol.
1966 Jul
Pulmonary edema: a complication of metaraminol treatment of paroxysmal supraventricular tachycardia.
1974 May
[Prinzmetal's angina induced by dopamine and metaraminol. 2 cases].
1979 Mar
Cerebral arteriovenous malformations, steal, and the hypertensive breakthrough threshold. An experimental study in rats.
1987 Apr
An extravascular hydraulic system to control blood pressure by a feedback regulation of the venous return.
1987 May
[Metaraminol in therapy of various forms of priapism].
1988 Jul
[Papaverine-induced priapism. Experiences with a new urologic emergency].
1989 Feb 10
[Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test].
1989 May 20
Reversible segmental left-ventricular dysfunction caused by accidental administration of sympathomimetic drug in human.
1997 Aug 29
Dynamic left ventricular outflow tract obstruction in critically ill patients.
2002 Sep
Hemodynamic pharmacology of intravenous vasopressors.
2003 Aug
Prophylactic i.v. metaraminol during spinal anesthesia for elective Cesarean delivery.
2003 Oct
Use of alpha-agonists for management of anaphylaxis occurring under anaesthesia: case studies and review.
2004 Dec
Fluid preload in obstetric patients. How to do it?
2004 Feb
A novel electrophilic synthesis and evaluation of medium specific radioactivity (1R,2S)-4-[18F]fluorometaraminol, a tracer for the assessment of cardiac sympathetic nerve integrity with PET.
2004 Jan
[Experimental study on prevention and treatment of focal segmental glomerulosclerosis with heparin].
2004 Jan
Induction of tumour blood flow stasis and necrosis: a new function for epinephrine similar to that of combretastatin A-4 derivative AVE8062 (AC7700).
2004 Jan 26
Inadvertent epidural administration of metaraminol.
2004 Jun
GABA-mediated attenuation of noradrenaline release in the rat median preoptic area caused by intravenous injection of metaraminol.
2004 Mar 31
Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol.
2004 Mar-Apr
Cerebellar interpositus nuclear inputs impinge on paraventricular neurons of the hypothalamus in rats.
2004 Nov 3
Photostability of symphatomimetic agents in commonly used infusion media in the absence and presence of bisulfite.
2004 Nov-Dec
Cardiovascular aspects of anaphylaxis: implications for treatment and diagnosis.
2005 Aug
Growth of Staphylococcus epidermidis in anaesthetic resuscitative drugs: implications for potential contamination.
2005 Feb
Metaraminol (Aramine) in the management of a significant amlodipine overdose.
2005 Jul
Norepinephrine and metaraminol in septic shock: a comparison of the hemodynamic effects.
2005 May
Vasoactive drugs in the intensive care unit.
2005 Oct
Use of metaraminol in patients with Familial Mediterranean Fever.
2006 Aug
[Diagnosis and treatment of priapism due to neoplasma of penis].
2006 Feb
Planar chromatographic analysis and quantification of short-lived radioactive metabolites from microdialysis fractions.
2006 Mar 3
Effect of induction agent on vasopressor and steroid use, and outcome in patients with septic shock.
2007
The blood-brain barrier for catecholamines - revisited.
2007 Apr
Effect of dopamine and metaraminol on the renal function of patients with septic shock.
2007 Apr 20
[Anesthesia for cesarean section in a patient with familiar hypertrophic cardiomyopathy: case report.].
2007 Dec
"Orpheus" cardiopulmonary bypass simulation system.
2007 Dec
Pharmacokinetic study of three cardiovascular drugs by high-performance liquid chromatography using pre-column derivatization with 9,10-anthraquinone-2-sulfonyl chloride.
2007 Oct 15
Sickle cell trait and priapism: a case report and review of the literature.
2008 Dec 30
Amniotic fluid embolism during vaginal delivery under analgesia. Case report.
2008 Jul-Aug
[Diagnosis and treatment of priapism: a report of 15 cases].
2008 Sep
Transient transmural ischaemia during endobronchial laser treatment: possible coronary artery embolism.
2008 Sep
Ventricular arrhythmias and antioxidative medication: experimental study.
2008 Sep-Oct
Mollaret meningitis may be caused by reactivation of latent cerebral toxoplasmosis.
2009
Discovery of highly potent and selective biphenylacylsulfonamide-based beta3-adrenergic receptor agonists and molecular modeling based on the solved X-ray structure of the beta2-adrenergic receptor: part 6.
2009 Aug 15
Which vasopressor for caesarean section?
2009 Dec
Is propofol a safe and effective sedative for relocating hip prostheses?
2009 Jan
Myocardial infarction associated with the administration of intravenous ephedrine and metaraminol for spinal-induced hypotension.
2009 May
Vasopressor choice for hypotension in elective Cesarean section: ephedrine or phenylephrine?
2010 Apr 30
Adenosine-induced cardiopulmonary arrest in a patient with paroxysmal supraventricular tachycardia--a response.
2010 May
Disparities of care for African-Americans and Caucasians with community-acquired pneumonia: a retrospective cohort study.
2010 May 27
Patents

Sample Use Guides

Intramuscular or Subcutaneous Injection: The recommended dose is 2 to 10 mg (0.2 to 1 mL). As with other agents given subcutaneously, only the preferred sites of injection, as set forth in standard texts, should be used. Intravenous Infusion: The recommended dose is 15 to 100 mg (1.5 to 10 mL) in 500 mL of Sodium Chloride Injection or 5% Dextrose Injection, adjusting the rate of infusion to maintain the blood pressure at the desired level. Higher concentrations of metaraminol, 150 to 500 mg per 500 mL of infusion fluid, have been used.
Route of Administration: Other
In Vitro Use Guide
Unknown
Name Type Language
METARAMINOL
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
METARAMINOL [MI]
Common Name English
METARAMINOL [HSDB]
Common Name English
METARAMINOL [WHO-DD]
Common Name English
METARAMINOL [INN]
Common Name English
METARAMINOL [VANDF]
Common Name English
BENZENEMETHANOL, ALPHA-(1-AMINOETHYL)-3-HYDROXY-, (R-(R*,S*))-
Common Name English
Classification Tree Code System Code
WHO-ATC C01CA09
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
NCI_THESAURUS C29709
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
WHO-VATC QC01CA09
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
Code System Code Type Description
CAS
54-49-9
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
PUBCHEM
5906
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
MERCK INDEX
M7273
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY Merck Index
IUPHAR
7229
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
FDA UNII
818U2PZ2EH
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
EVMPD
SUB08815MIG
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
NCI_THESAURUS
C61835
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
MESH
D008680
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
WIKIPEDIA
METARAMINOL
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
INN
34
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
RXCUI
6805
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY RxNorm
EPA CompTox
54-49-9
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
CAS
7619-17-2
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
DRUG BANK
DB00610
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
HSDB
2716
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201319
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY
DRUG CENTRAL
1721
Created by admin on Sat Jun 26 00:29:19 UTC 2021 , Edited by admin on Sat Jun 26 00:29:19 UTC 2021
PRIMARY