Page last updated: 2024-11-04

metaraminol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

Metaraminol: A sympathomimetic agent that acts predominantly at alpha-1 adrenergic receptors. It has been used primarily as a vasoconstrictor in the treatment of HYPOTENSION. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

metaraminol : A member of the class of phenylethanolamines that is 2-amino-1-phenylethanol substituted by a methyl group at position 2 and a phenolic hydroxy group at position 1. A sympathomimetic agent , it is used in the treatment of hypotension. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5906
CHEMBL ID1201319
CHEBI ID6794
SCHEMBL ID136778
MeSH IDM0013526

Synonyms (62)

Synonym
3-[(1r,2s)-2-amino-1-hydroxypropyl]phenol
1-alpha-(1-aminoethyl)-m-hydroxybenzyl alcohol
pressonex
alpha-(1-aminoethyl)-m-hydroxybenzyl alcohol
metaradrine
icoral b
metaraminol [inn:ban]
metaraminolum [inn-latin]
metaraminolum [latin]
m-hydroxy-alpha-(1-aminoethyl)-benzyl alcohol
benzenemethanol, alpha-(1-aminoethyl)-3-hydroxy-, (r-(r*,s*))-
hsdb 2716
benzyl alcohol, alpha-(1-aminoethyl)-m-hydroxy-, (-)-
C07146
metaraminol
54-49-9
alpha-(m-hydroxyphenyl)-beta-aminopropanol
2-amino-1-(m-hydroxyphenyl)-1-propanol
(-)-erythro-metaraminol
DB00610
alpha-(1-aminoethyl)-3-hydroxybenzenemethanol
m-hydroxy norephedrine
m-hydroxypropadrine
1-metaraminol
hydroxynorephedrine
3-hydroxyphenylisopropanolamine
1-(m-hydroxyphenyl)-2-amino-1-propanol
l-metaraminol
m-hydroxyphenylpropanolamine
NCGC00178024-01
NCGC00178024-02
CHEBI:6794 ,
metaraminolum
metaraminol (inn)
D08192
CHEMBL1201319
AKOS006277341
ccris 8465
unii-818u2pz2eh
818u2pz2eh ,
alpha-(1-aminoethyl)-m-hydroxybenzyl alcohol, (-)-erythro-
DN43400000
(1r,2s)-metaraminol
niosh/dn4340000
(-)-erythro-methraminol
benzyl alcohol, alpha-(1-aminoethyl)-m-hydroxy-, (-)-erythro-
metaraminol [vandf]
metaraminol [who-dd]
metaraminol [inn]
metaraminol [hsdb]
metaraminol [mi]
gtpl7229
SCHEMBL136778
(ar)-a-[(1s)-1-aminoethyl]-3-hydroxy-benzenemethanol
J-501788
DTXSID8023268
J-510372
SBI-0206715.P001
3-((1r,2s)-2-amino-1-hydroxypropyl)phenol
Q409981
54-49-9 (free)
EN300-7455644

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" The safe preparation of medications during resuscitation requires attention, time and resources, and can be a source of medication error."( Predrawn prehospital medications are microbiologically safe for up to 48 hours.
Foster, A; Garner, A; Gutierrez, CH; Kitcher, J; Soeyland, T; Vidler, S, 2018
)
0.48
"Predrawing of the eight studied medications for urgent prehospital procedures appears to be a microbiologically safe practice with syringe dwell times up to 48 hours."( Predrawn prehospital medications are microbiologically safe for up to 48 hours.
Foster, A; Garner, A; Gutierrez, CH; Kitcher, J; Soeyland, T; Vidler, S, 2018
)
0.48

Pharmacokinetics

ExcerptReferenceRelevance
" This method was successfully applied to the analysis of the three drugs in rat plasma and their pharmacokinetic studies."( Pharmacokinetic study of three cardiovascular drugs by high-performance liquid chromatography using pre-column derivatization with 9,10-anthraquinone-2-sulfonyl chloride.
Cui, S; Feng, F; Liu, H; Ma, M; Xie, D; Xu, S, 2007
)
0.34

Dosage Studied

In isolated aortic rings the dose-response curve for (-)metaraminol was not parallel to that of (-)epinephrine, (-)norepinephrine or (-)phenylephrine.

ExcerptRelevanceReference
" NA (30, 50 micrograms) also produced similar effects to those of 5HT, but DA at the same dosage produced no significant changes in the amplitude and discharge rate of spikes."( Effects of intraventricularly administered serotonin, noradrenaline, dopamine and metaraminol on the reserpine-induced spikes recorded from the medial nucleus trapezoides in rabbits.
Kimura, K; Kimura, Y; Ohata, K; Takagi, H, 1979
)
0.26
" After exact dosage adjustment the danger of drug-induced priapism is low."( [Priapism following intracavernous injection of vasoactive substances as a urologic emergency].
Papadopoulos, I; Wand, H; Weichert-Jacobsen, K, 1990
)
0.28
" In isolated aortic rings the dose-response curve for (-)metaraminol was not parallel to that of (-)epinephrine, (-)norepinephrine or (-)phenylephrine."( Heterogeneity of alpha 1 receptors associated with vascular smooth muscle: evidence from functional and ligand binding studies.
Babich, M; Butler, BT; Pedigo, NW; Piascik, MT, 1987
)
0.27
" Pharmacokinetic data for drugs administered endotracheally are lacking; therefore, dosage recommendations are empirical."( Endotracheal drug therapy in cardiopulmonary resuscitation.
Raehl, CL, 1986
)
0.27
"We studied dosage optimization for metaraminol when managing hypotension during subarachnoid anaesthesia."( A study to determine the optimum dose of metaraminol required to increase blood pressure by 25% during subarachnoid anaesthesia.
Cheng, JH; Critchley, JA; Critchley, LA; Karmakar, MK, 1999
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
alpha-adrenergic agonistAn agent that selectively binds to and activates alpha-adrenergic receptors.
sympathomimetic agentA drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
vasoconstrictor agentDrug used to cause constriction of the blood vessels.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
phenylethanolaminesAn ethanolamine compound having a phenyl (substituted or unsubstituted) group on the carbon bearing the hydroxy substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)1,000.00000.11007.190310.0000AID1449628
Macrophage migration inhibitory factorHomo sapiens (human)IC50 (µMol)98.10000.03803.09109.8000AID1877334
Macrophage migration inhibitory factorHomo sapiens (human)Ki77.10000.03802.22565.5500AID1877338
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (57)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
prostaglandin biosynthetic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of cytokine productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of mature B cell apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
inflammatory responseMacrophage migration inhibitory factorHomo sapiens (human)
cell surface receptor signaling pathwayMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of cell population proliferationMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of gene expressionMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of protein kinase A signalingMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of macrophage chemotaxisMacrophage migration inhibitory factorHomo sapiens (human)
carboxylic acid metabolic processMacrophage migration inhibitory factorHomo sapiens (human)
DNA damage response, signal transduction by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of cell migrationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of B cell proliferationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of lipopolysaccharide-mediated signaling pathwayMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of tumor necrosis factor productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of myeloid cell apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
regulation of macrophage activationMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of apoptotic processMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of DNA damage response, signal transduction by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
innate immune responseMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of fibroblast proliferationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylationMacrophage migration inhibitory factorHomo sapiens (human)
positive chemotaxisMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of protein metabolic processMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of prostaglandin secretion involved in immune responseMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of myeloid leukocyte cytokine production involved in immune responseMacrophage migration inhibitory factorHomo sapiens (human)
protein homotrimerizationMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of arachidonic acid secretionMacrophage migration inhibitory factorHomo sapiens (human)
cellular senescenceMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damage by p53 class mediatorMacrophage migration inhibitory factorHomo sapiens (human)
positive regulation of chemokine (C-X-C motif) ligand 2 productionMacrophage migration inhibitory factorHomo sapiens (human)
negative regulation of cellular senescenceMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
protease bindingMacrophage migration inhibitory factorHomo sapiens (human)
dopachrome isomerase activityMacrophage migration inhibitory factorHomo sapiens (human)
cytokine activityMacrophage migration inhibitory factorHomo sapiens (human)
cytokine receptor bindingMacrophage migration inhibitory factorHomo sapiens (human)
protein bindingMacrophage migration inhibitory factorHomo sapiens (human)
chemoattractant activityMacrophage migration inhibitory factorHomo sapiens (human)
identical protein bindingMacrophage migration inhibitory factorHomo sapiens (human)
phenylpyruvate tautomerase activityMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
extracellular regionMacrophage migration inhibitory factorHomo sapiens (human)
extracellular spaceMacrophage migration inhibitory factorHomo sapiens (human)
nucleoplasmMacrophage migration inhibitory factorHomo sapiens (human)
cytoplasmMacrophage migration inhibitory factorHomo sapiens (human)
cytosolMacrophage migration inhibitory factorHomo sapiens (human)
plasma membraneMacrophage migration inhibitory factorHomo sapiens (human)
cell surfaceMacrophage migration inhibitory factorHomo sapiens (human)
vesicleMacrophage migration inhibitory factorHomo sapiens (human)
secretory granule lumenMacrophage migration inhibitory factorHomo sapiens (human)
extracellular exosomeMacrophage migration inhibitory factorHomo sapiens (human)
ficolin-1-rich granule lumenMacrophage migration inhibitory factorHomo sapiens (human)
extracellular spaceMacrophage migration inhibitory factorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID1877335Reversal inhibition of MIF tautomerase (unknown origin) at 0.5 mM using 4-HPP as substrate preincubated for 30 min followed by 100 fold dilution by dilution assay2022Bioorganic & medicinal chemistry letters, 01-01, Volume: 55Repurposing old drugs as novel inhibitors of human MIF from structural and functional analysis.
AID1877338Inhibition of MIF tautomerase (unknown origin) using 4-HPP as substrate preincubated for 1 hr followed by substrate addition by Lineweaver-Burk plot anlysis2022Bioorganic & medicinal chemistry letters, 01-01, Volume: 55Repurposing old drugs as novel inhibitors of human MIF from structural and functional analysis.
AID1877334Inhibition of MIF tautomerase (unknown origin) using 4-HPP as substrate preincubated for 1 hr followed by substrate addition2022Bioorganic & medicinal chemistry letters, 01-01, Volume: 55Repurposing old drugs as novel inhibitors of human MIF from structural and functional analysis.
AID174334Neuronal selectivity expressed as Concentration in left atrium after iv administration in rat, pretreated with 6-hydroxydopamine (control = 5.26+/-0.43)1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID174338Neuronal selectivity expressed as Concentration in right atrium after iv administration in rat, pretreated with 6-hydroxydopamine (control = 5.19+/-0.14)1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID173071Percent change in thallium-201 concentration in blood of sympathectomized rat, pretreated with 6-hydroxydopamine1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID173072Percent change in thallium-201 concentration in left ventricle of sympathectomized rat, pretreated with 6-hydroxydopamine1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID171205Percente change in thallium-201 concentration in left atrium of sympathectomized rat, pretreated with 6-hydroxydopamine1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID174468Neuronal selectivity expressed as Concentration in spleen after iv administration in rat, pretreated with 6-hydroxydopamine (control = 1.88+/-0.25)1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID173073Percent change in thallium-201 concentration in right atrium of sympathectomized rat, pretreated with 6-hydroxydopamine1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID678715Inhibition of human CYP2D6 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 4-methylaminoethyl-7-methoxycoumarin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID63447Tissue concentration in dog left ventricle to blood ratio 24 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID173074Percent change in thallium-201 concentration in spleen of sympathectomized rat, pretreated with 6-hydroxydopamine1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID678713Inhibition of human CYP2C9 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 7-methoxy-4-trifluoromethylcoumarin-3-acetic acid as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID63450Tissue concentration in dog liver 0.5 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID678712Inhibition of human CYP1A2 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using ethoxyresorufin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID678721Metabolic stability in human liver microsomes assessed as GSH adduct formation at 100 uM after 90 mins by HPLC-MS analysis2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID63438Tissue concentration in dog blood 24 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID63440Tissue concentration in dog heart 0.5 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID63461Tissue concentration in dog spleen 24 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID678714Inhibition of human CYP2C19 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 3-butyryl-7-methoxycoumarin as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID63454Tissue concentration in dog lung 24 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID174337Neuronal selectivity expressed as Concentration in left ventricle after iv administration in rat, pretreated with 6-hydroxydopamine (control = 5.38+/-0.39)1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID174332Neuronal selectivity expressed as Concentration in blood after iv administration in rat, pretreated with 6-hydroxydopamine (control = 0.062+/-0.012)1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID63449Tissue concentration in dog left ventricle to blood ratio 0.5 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID173075Percent change in thallium-201 in concentration right ventricle of sympathectomized rat, pretreated with 6-hydroxydopamine1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID63453Tissue concentration in dog lung 0.5 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID63460Tissue concentration in dog spleen 0.5 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID63451Tissue concentration in dog liver 24 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID174340Neuronal selectivity expressed as Concentration in right ventricle after iv administration in rat, pretreated with 6-hydroxydopamine (control = 6.10+/-0.45)1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID227700Anticonvulsant activity2003Bioorganic & medicinal chemistry letters, Aug-18, Volume: 13, Issue:16
Topological virtual screening: a way to find new anticonvulsant drugs from chemical diversity.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID678722Covalent binding affinity to human liver microsomes assessed per mg of protein at 10 uM after 60 mins presence of NADPH2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID678716Inhibition of human CYP3A4 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using diethoxyfluorescein as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1877336Cytotoxicity against mouse RAW264.7 cells assessed as reduction in cell viability up to 100 uM by CCK8 assay2022Bioorganic & medicinal chemistry letters, 01-01, Volume: 55Repurposing old drugs as novel inhibitors of human MIF from structural and functional analysis.
AID63441Tissue concentration in dog heart 24 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID1877333Inhibition of inhibition of MIF tautomerase (unknown origin) in MIF-induced mouse RAW264.7 cells assessed as reduction in cell migration relative to control2022Bioorganic & medicinal chemistry letters, 01-01, Volume: 55Repurposing old drugs as novel inhibitors of human MIF from structural and functional analysis.
AID63437Tissue concentration in dog blood 0.5 hr after iv administration1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
Neuronal mapping of the heart with 6-[18F]fluorometaraminol.
AID1877340Non-competitive inhibition of MIF tautomerase (unknown origin) using 4-HPP as substrate preincubated for 1 hr followed by substrate addition by Lineweaver-Burk plot anlysis2022Bioorganic & medicinal chemistry letters, 01-01, Volume: 55Repurposing old drugs as novel inhibitors of human MIF from structural and functional analysis.
AID678717Inhibition of human CYP3A4 assessed as ratio of IC50 in absence of NADPH to IC50 for presence of NADPH using 7-benzyloxyquinoline as substrate after 30 mins2012Chemical research in toxicology, Oct-15, Volume: 25, Issue:10
Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (929)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990798 (85.90)18.7374
1990's55 (5.92)18.2507
2000's38 (4.09)29.6817
2010's26 (2.80)24.3611
2020's12 (1.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials25 (2.52%)5.53%
Reviews48 (4.84%)6.00%
Case Studies63 (6.35%)4.05%
Observational3 (0.30%)0.25%
Other853 (85.99%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (6)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Up-Down Determination of the ED90 of Metaraminol to Treat Hypotension During Elective Cesarean Section [NCT01108874]Phase 248 participants (Anticipated)Interventional2009-11-30Completed
Platform Adaptive Embedded Trial for Acute Respiratory Distress Syndrome [NCT05658692]Phase 41,000 participants (Anticipated)Interventional2022-10-01Recruiting
Effect of Three Weight-adjusted Vasopressors for With Combined Spinal-Epidural Anesthesia for Elective Cesarean Delivery: A Randomized Controlled Trial [NCT04991662]Phase 478 participants (Actual)Interventional2021-10-10Completed
Ephedrine, Phenylephrine and Metaraminol Effects on Maternal Cardiac Output, Uterine Blood Flow and Fetal Circulation in Patients With Preeclampsia Under Spinal Anesthesia for Cesarean [NCT02245191]60 participants (Actual)Interventional2014-07-31Active, not recruiting
Maternal and Neonatal Outcomes After the Use of Vasopressors to Correct Hypotension During Cesarean Section Under Spinal Anesthesia in Pregnant Women With Severe Preeclampsia: Randomized Clinical Trial [NCT01451060]Phase 30 participants (Actual)Interventional2011-06-30Withdrawn(stopped due to We didn't have enough financial support)
Effect of 90% Effective Dose of Metaraminol in Supine and Left Tilt Positions on Cesarean Section:A Non-inferiority Trial [NCT05084599]Phase 4124 participants (Anticipated)Interventional2022-04-01Not yet recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]