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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13NO2
Molecular Weight 167.205
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METARAMINOL

SMILES

C[C@H](N)[C@H](O)C1=CC(O)=CC=C1

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
Myocardial infarction induced by metaraminol bitartrate (aramine).
1966 Oct
[Papaverine-induced priapism. Experiences with a new urologic emergency].
1989 Feb 10
The effect of intracarotid nonionic contrast media on the blood-brain barrier in acute hypertension.
1994 Jan
Anaphylactic or anaphylactoid reactions in patients undergoing cardiac surgery.
2001 Dec
Assessment of cardiac sympathetic nerve integrity with positron emission tomography.
2001 Jul
Prostaglandin synthesis inhibitor improves hypotension during normothermic cardiopulmonary bypass.
2001 Nov-Dec
The effect of prophylactic metaraminol on systemic hypotension caused by induction of anaesthesia with propofol in patients over 55 years old.
2001 Sep
Metaraminol infusion for maintenance of arterial blood pressure during spinal anesthesia for cesarean delivery: the effect of a crystalloid bolus.
2001 Sep
Relative uptake, metabolism, and beta-receptor binding of (1R,2S)-4-(18)F-fluorometaraminol and (123)I-MIBG in normotensive and spontaneously hypertensive rats.
2002 Mar
Hemodynamic pharmacology of intravenous vasopressors.
2003 Aug
A Japanese case of familial Mediterranean fever with family history demonstrating a mutation in MEFV.
2003 Aug
Prophylactic i.v. metaraminol during spinal anesthesia for elective Cesarean delivery.
2003 Oct
[Preload during spinal anesthesia for cesarean section: comparison between crystalloid and colloid solutions.].
2004 Dec
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
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
Effect of induction agent on vasopressor and steroid use, and outcome in patients with septic shock.
2007
[Anesthesia for cesarean section in a patient with familiar hypertrophic cardiomyopathy: case report.].
2007 Dec
A prospective comparison of vasopressor requirement and hemodynamic changes during spinal anesthesia for cesarean delivery in patients with multiple gestation versus singleton pregnancy.
2007 Feb
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
Myocardial infarction associated with the administration of intravenous ephedrine and metaraminol for spinal-induced hypotension.
2009 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 [INN]
Common Name English
METARAMINOL [VANDF]
Common Name English
BENZENEMETHANOL, ALPHA-(1-AMINOETHYL)-3-HYDROXY-, (R-(R*,S*))-
Common Name English
Metaraminol [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC C01CA09
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
NCI_THESAURUS C29709
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
WHO-VATC QC01CA09
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
Code System Code Type Description
CAS
54-49-9
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
PUBCHEM
5906
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
MERCK INDEX
M7273
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY Merck Index
IUPHAR
7229
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
FDA UNII
818U2PZ2EH
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
EVMPD
SUB08815MIG
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
NCI_THESAURUS
C61835
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
MESH
D008680
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
WIKIPEDIA
METARAMINOL
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
INN
34
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
RXCUI
6805
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY RxNorm
EPA CompTox
DTXSID8023268
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
DAILYMED
818U2PZ2EH
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
CHEBI
6794
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
CAS
7619-17-2
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
NON-SPECIFIC STEREOCHEMISTRY
DRUG BANK
DB00610
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
HSDB
2716
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
ChEMBL
CHEMBL1201319
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY
DRUG CENTRAL
1721
Created by admin on Fri Dec 16 19:39:50 UTC 2022 , Edited by admin on Fri Dec 16 19:39:50 UTC 2022
PRIMARY