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	C4H6O6
Molecular Weight	150.0868
Charge	0
Count

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

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

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 2662

Conditions

Condition	Modality	Highest Phase	Product
Acute hypotensive state 3 Sources: http://www.druginformation.com/RxDrugs/M/Metaraminol%20Bitartrate%20Injection.html	Preventing	Approved 8360	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 8360	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 8360	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 503	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 1579	inhibitor 1752	inhibitor 1837

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BSEP 401 CYP1A2 1509 CYP2C19 1463 OATP1B1 781 OATP1B3 700

Drug as perpetrator

Target	Modality	Activity
BSEP 402	inhibitor 3240 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50239972, https://pubmed.ncbi.nlm.nih.gov/22961681/	no [IC50 >1000 uM]
OATP1B1 796	inhibitor 3240 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 709	inhibitor 3240 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 1673	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C19 1537	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C9 1803	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEzMTkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2D6 1875	inhibitor 3240 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTIwMTMxOSJ9fQ%3D%3D, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A4 1909	inhibitor 3240 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
SHOCK CAUSED BY CONTINUOUS INFUSION OF METARAMINOL BITARTRATE (ARAMINE).	1964 Feb 1	14122464
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
[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
An extravascular hydraulic system to control blood pressure by a feedback regulation of the venous return.	1987 May	3652100
Post-traumatic priapism treated with metaraminol bitartrate: case report.	1990 Dec	2258979
The effect of intracarotid nonionic contrast media on the blood-brain barrier in acute hypertension.	1994 Jan	8141072
Comparison of metaraminol and ephedrine infusions for maintaining arterial pressure during spinal anesthesia for elective cesarean section.	2001 Aug	11506099
Assessment of cardiac sympathetic nerve integrity with positron emission tomography.	2001 Jul	11516699
Synthesis of high-specific-radioactivity 4- and 6-[18F]fluorometaraminol-PET tracers for the adrenergic nervous system of the heart.	2001 Mar	11310603
Prostaglandin synthesis inhibitor improves hypotension during normothermic cardiopulmonary bypass.	2001 Nov-Dec	11730209
PEA I and PEA II based implantable haemodynamic monitor: pre clinical studies in sheep.	2002 Jan	11846317
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	11884497
Dynamic left ventricular outflow tract obstruction in critically ill patients.	2002 Sep	16573425
Hemodynamic pharmacology of intravenous vasopressors.	2003 Aug	12961786
The incidence and management of priapism in Western Australia: a 16 year audit.	2003 Aug	12934055
A Japanese case of familial Mediterranean fever with family history demonstrating a mutation in MEFV.	2003 Aug	12924509
Drinking attenuates the noradrenaline release in the lateral hypothalamic area induced by angiotensin II activation of the subfornical organ in rats.	2003 Mar 18	12644277
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
Use of alpha-agonists for management of anaphylaxis occurring under anaesthesia: case studies and review.	2004 Dec	15549981
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
[Experimental study on prevention and treatment of focal segmental glomerulosclerosis with heparin].	2004 Jan	14706199
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	14735207
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
Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol.	2004 Mar-Apr	15703094
Cerebellar interpositus nuclear inputs impinge on paraventricular neurons of the hypothalamus in rats.	2004 Nov 3	15489011
Photostability of symphatomimetic agents in commonly used infusion media in the absence and presence of bisulfite.	2004 Nov-Dec	15663061
Growth of Staphylococcus epidermidis in anaesthetic resuscitative drugs: implications for potential contamination.	2005 Feb	15957694
Norepinephrine and metaraminol in septic shock: a comparison of the hemodynamic effects.	2005 May	15803299
Vasoactive drugs in the intensive care unit.	2005 Oct	16175026
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
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
"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
Ventricular arrhythmias and antioxidative medication: experimental study.	2008 Sep-Oct	18846922
Which vasopressor for caesarean section?	2009 Dec	20081625
Impact of admixture time and diluent order on metaraminol concentration.	2009 Sep	19777670
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 `Wed Jul 05 22:40:50 UTC 2023` Edited by `admin` on `Wed Jul 05 22:40:50 UTC 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