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
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
[Metaraminol--an antidote in corpus cavernosum autoinjection therapy-induced prolonged erection].	1986 May	2426857
Cerebral arteriovenous malformations, steal, and the hypertensive breakthrough threshold. An experimental study in rats.	1987 Apr	3559722
An extravascular hydraulic system to control blood pressure by a feedback regulation of the venous return.	1987 May	3652100
Assessment of the permeability of the blood-retinal barrier in hypertensive rats.	1987 Oct	3653967
[Metaraminol in therapy of various forms of priapism].	1988 Jul	3140463
The metaraminol test and adverse cardiac effects.	1989 Aug 1	2751185
[Papaverine-induced priapism. Experiences with a new urologic emergency].	1989 Feb 10	2917481
[Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test].	1989 May 20	2524805
Post-traumatic priapism treated with metaraminol bitartrate: case report.	1990 Dec	2258979
[Familial Mediterranean fever. The metaraminol test as a cause of severe cephalalgia].	1990 Jun	2244064
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
Dynamic left ventricular outflow tract obstruction in critically ill patients.	2002 Sep	16573425
[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
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
Meningismus after metaraminol administration in a patient with Familial Mediterranean fever.	2006 Oct	16987863
[Effect of fluid resuscitation on adhesion molecule and hemodynamics in patients with severe sepsis].	2006 Sep	16959151
Effect of induction agent on vasopressor and steroid use, and outcome in patients with septic shock.	2007	17506873
The blood-brain barrier for catecholamines - revisited.	2007 Apr	17449463
Effect of dopamine and metaraminol on the renal function of patients with septic shock.	2007 Apr 20	17517184
[Anesthesia for cesarean section in a patient with familiar hypertrophic cardiomyopathy: case report.].	2007 Dec	19462143
"Orpheus" cardiopulmonary bypass simulation system.	2007 Dec	18293807
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	17242099
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	17766197
Sickle cell trait and priapism: a case report and review of the literature.	2008 Dec 30	19116025
Amniotic fluid embolism during vaginal delivery under analgesia. Case report.	2008 Jul-Aug	19378589
[Diagnosis and treatment of priapism: a report of 15 cases].	2008 Sep	18998470
Transient transmural ischaemia during endobronchial laser treatment: possible coronary artery embolism.	2008 Sep	18853597
Ventricular arrhythmias and antioxidative medication: experimental study.	2008 Sep-Oct	18846922
Mollaret meningitis may be caused by reactivation of latent cerebral toxoplasmosis.	2009	19922380
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	19608416
Which vasopressor for caesarean section?	2009 Dec	20081625
Is propofol a safe and effective sedative for relocating hip prostheses?	2009 Jan	19104094
Myocardial infarction associated with the administration of intravenous ephedrine and metaraminol for spinal-induced hypotension.	2009 May	19413828
Impact of admixture time and diluent order on metaraminol concentration.	2009 Sep	19777670
Vasopressor choice for hypotension in elective Cesarean section: ephedrine or phenylephrine?	2010 Apr 30	22371756
Molecular imaging of cardiac sympathetic innervation by 11C-mHED and PET: from man to mouse?	2010 Aug	20679472
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
Disparities of care for African-Americans and Caucasians with community-acquired pneumonia: a retrospective cohort study.	2010 May 27	20507628
[Determination of three adrenergic drugs using capillary electrophoresis with amperometric detection].	2010 Nov	21381427

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