METARAMINOL

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 Search

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

Description
Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html | https://www.ncbi.nlm.nih.gov/pubmed/9663612 | https://www.ncbi.nlm.nih.gov/pubmed/15703094

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9663612	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Acute hypotensive state 3 Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html	Preventing	Approved 8429	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.
Hemorrhage 11 Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html	Palliative	Approved 8429	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.
Shock 9 Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html	Palliative	Approved 8429	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.
Priapism 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15703094	Primary	Not Provided 504	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/2751185	unhealthy, 38 years n = 1 Health Status: unhealthy Age Group: 38 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2751185	Disc. AE: Bigeminal rhythm... AEs leading to discontinuation/dose reduction: Bigeminal rhythm (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2751185

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/2751185	unhealthy, 38 years n = 1 Health Status: unhealthy Age Group: 38 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2751185

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 402 CYP1A2 1524 CYP2C19 1478 OATP1B1 788 OATP1B3 706

Drug as perpetrator

Target	Modality	Activity
BSEP 403	inhibitor 3277 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50239972, https://pubmed.ncbi.nlm.nih.gov/22961681/	no [IC50 >1000 uM]
OATP1B1 803	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIwNjIyNjIifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 715	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIwNjIyNjIifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTIwMTMxOSJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTIwMTMxOSJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6794	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6794
ZINC	ZINC000000001695	http://zinc15.docking.org/substances/ZINC000000001695

PubMed

Title	Date	PubMed
Augmented natriuretic response to infusion of saline in dogs rendered acutely hypertensive with metaraminol.	1966 Jul	5918955
Myocardial infarction induced by metaraminol bitartrate (aramine).	1966 Oct	6009556
Pulmonary edema: a complication of metaraminol treatment of paroxysmal supraventricular tachycardia.	1974 May	4415385
[Prinzmetal's angina induced by dopamine and metaraminol. 2 cases].	1979 Mar	491823
The metaraminol test and adverse cardiac effects.	1989 Aug 1	2751185
The effect of intracarotid nonionic contrast media on the blood-brain barrier in acute hypertension.	1994 Jan	8141072
Reversible segmental left-ventricular dysfunction caused by accidental administration of sympathomimetic drug in human.	1997 Aug 29	9292339
A comparative study of three different methods of administering metaraminol during spinal anaesthesia in the elderly.	2001 Apr	11314833
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section.	2001 Aug	11506099
Methanol solvent may cause increased apparent metabolic instability in in vitro assays.	2001 Feb	11159810
Synthesis of high-specific-radioactivity 4- and 6-[18F]fluorometaraminol-PET tracers for the adrenergic nervous system of the heart.	2001 Mar	11310603
Randomized controlled study of colloid preload before spinal anaesthesia for caesarean section.	2001 Nov	11878530
Cardiovascular aspects of anaphylaxis: implications for treatment and diagnosis.	2005 Aug	15985820
Growth of Staphylococcus epidermidis in anaesthetic resuscitative drugs: implications for potential contamination.	2005 Feb	15957694
Mollaret meningitis may be caused by reactivation of latent cerebral toxoplasmosis.	2009	19922380
Is propofol a safe and effective sedative for relocating hip prostheses?	2009 Jan	19104094
Impact of admixture time and diluent order on metaraminol concentration.	2009 Sep	19777670
Cardiac arrest in intensive care unit: Case report and future recommendations.	2010 Jan	20668565
Adenosine-induced cardiopulmonary arrest in a patient with paroxysmal supraventricular tachycardia--a response.	2010 May	20466244
Disparities of care for African-Americans and Caucasians with community-acquired pneumonia: a retrospective cohort study.	2010 May 27	20507628

Patents

Sample Use Guides

In Vivo Use Guide

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

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