METARAMINOL BITARTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H13NO2.C4H6O6
Molecular Weight	317.2919
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VENXSELNXQXCNT-IJYXXVHRSA-N

InChI=1S/C9H13NO2.C4H6O6/c1-6(10)9(12)7-3-2-4-8(11)5-7;5-1(3(7)8)2(6)4(9)10/h2-6,9,11-12H,10H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t6-,9-;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula	C9H13NO2
Molecular Weight	167.205
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Myocardial infarction induced by metaraminol bitartrate (aramine).	1966 Oct	6009556
Vasopressor agents in shock.	1975 Apr	1039254
[Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test].	1989 May 20	2524805
Reversible segmental left-ventricular dysfunction caused by accidental administration of sympathomimetic drug in human.	1997 Aug 29	9292339
The influence of baricity on the haemodynamic effects of intrathecal bupivacaine 0.5%.	1999 May	10995146
Laparoscopic and open surgery for pheochromocytoma.	2001	11580870
A comparative study of three different methods of administering metaraminol during spinal anaesthesia in the elderly.	2001 Apr	11314833
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
Metaraminol infusion for maintenance of arterial blood pressure during spinal anesthesia for cesarean delivery: the effect of a crystalloid bolus.	2001 Sep	11524344
Isoflurane dosage for equivalent intraoperative electroencephalographic suppression in patients with and without epidural blockade.	2002 Nov	12401635
Prophylactic i.v. metaraminol during spinal anesthesia for elective Cesarean delivery.	2003 Oct	14525837
[Preload during spinal anesthesia for cesarean section: comparison between crystalloid and colloid solutions.].	2004 Dec	19471789
Fluid preload in obstetric patients. How to do it?	2004 Feb	19471706
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	14741575
Inadvertent epidural administration of metaraminol.	2004 Jun	15144319
GABA-mediated attenuation of noradrenaline release in the rat median preoptic area caused by intravenous injection of metaraminol.	2004 Mar 31	15109934
Photostability of symphatomimetic agents in commonly used infusion media in the absence and presence of bisulfite.	2004 Nov-Dec	15663061
Bench-to-bedside review: hyperinsulinaemia/euglycaemia therapy in the management of overdose of calcium-channel blockers.	2006	16732893
Use of metaraminol in patients with Familial Mediterranean Fever.	2006 Aug	16867110
[Diagnosis and treatment of priapism due to neoplasma of penis].	2006 Feb	16519158
Planar chromatographic analysis and quantification of short-lived radioactive metabolites from microdialysis fractions.	2006 Mar 3	16445924
Effect of induction agent on vasopressor and steroid use, and outcome in patients with septic shock.	2007	17506873
Transient transmural ischaemia during endobronchial laser treatment: possible coronary artery embolism.	2008 Sep	18853597
Cardiac arrest in intensive care unit: Case report and future recommendations.	2010 Jan	20668565
Clinical evaluation of the flotrac/Vigileo system for continuous cardiac output monitoring in patients undergoing regional anesthesia for elective cesarean section: a pilot study.	2010 Jun	20835557
Adenosine-induced cardiopulmonary arrest in a patient with paroxysmal supraventricular tachycardia--a response.	2010 May	20466244

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:00 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:00 GMT 2023`
Record UNII	ZC4202M9P3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METARAMINOL BITARTRATE

Common Name

English

METARAMINOL BITARTRATE [ORANGE BOOK]

Common Name

English

METARAMINOL BITARTRATE, (R-(R*,S*))-

Common Name

English

ARAMINE

Brand Name

English

METARAMINOL TARTRATE

Common Name

English

Metaraminol tartrate [WHO-DD]

Common Name

English

METARAMINOL BITARTRATE [USP IMPURITY]

Common Name

English

METARAMINOL BITARTRATE [USP-RS]

Common Name

English

METARAMINOL BITARTRATE [USP MONOGRAPH]

Common Name

English

NSC-758425

Code

English

(-)-.ALPHA.-(1-AMINOETHYL)-M-HYDROXYBENZYL ALCOHOL TARTRATE (1:1) (SALT)

Common Name

English

METARAMINOL TARTRATE [MART.]

Common Name

English

METARAMINOL BITARTRATE [MI]

Common Name

English

METARAMINOL BITARTRATE [JAN]

Common Name

English

METARAMINOL BITARTRATE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29709