metaraminol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1721 54-49-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • metaraminol bitartrate
  • (-)-Metaraminol
  • (-)-erythro-Metaraminol
  • (-)-m-Hydroxynorephedrine
  • metaradrine
  • l-Metaraminol
  • m-Hydroxynorephedrine
  • 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.
  • Molecular weight: 167.21
  • Formula: C9H13NO2
  • CLOGP: -0.08
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 3
  • TPSA: 66.48
  • ALOGS: -1.12
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
50 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 49.82 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
Sept. 29, 1954 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Mental status changes postoperative 70.87 55.85 9 308 206 53348543
Confusion postoperative 69.44 55.85 9 308 243 53348506

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC C01CA09 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
CARDIAC STIMULANTS EXCL. CARDIAC GLYCOSIDES
Adrenergic and dopaminergic agents
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D058646 Adrenergic alpha-1 Receptor Agonists
MeSH PA D000316 Adrenergic alpha-Agonists
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D013566 Sympathomimetics
MeSH PA D014662 Vasoconstrictor Agents
CHEBI has role CHEBI:35524 sympathomimetic
CHEBI has role CHEBI:35569 alpha-adrenergic receptor agonist

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Low blood pressure indication 45007003
Priapism off-label use 6273006 DOID:9286

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.51 acidic
pKa2 12.54 acidic
pKa3 8.86 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alpha-1A adrenergic receptor GPCR AGONIST WOMBAT-PK CHEMBL

External reference:

IDSource
4017958 VUID
N0000178937 NUI
D01019 KEGG_DRUG
33402-03-8 SECONDARY_CAS_RN
4017958 VANDF
4019818 VANDF
C0025575 UMLSCUI
CHEBI:6794 CHEBI
CHEMBL1201319 ChEMBL_ID
DB00610 DRUGBANK_ID
CHEMBL2062262 ChEMBL_ID
D008680 MESH_DESCRIPTOR_UI
5906 PUBCHEM_CID
34 INN_ID
7229 IUPHAR_LIGAND_ID
818U2PZ2EH UNII
6805 RXNORM
5061 MMSL
d00702 MMSL
001824 NDDF
004735 NDDF
372728001 SNOMEDCT_US
41015006 SNOMEDCT_US
58461000 SNOMEDCT_US

Pharmaceutical products:

None