metaraminol ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,ITK,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPKAPK2,NTRK2,PDK2,PIK3CB,PIM2,PRKDC,SIK2,STK33,SYK,TEK,TGFBR1,ZAP70 34
kinase-selectivity-class AXL,EIF2AK3,EPHB4,GRK2,MAP2K6 5
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 71.86 52.80 9 512 189 90627737
Confusion postoperative 69.72 52.80 9 512 242 90627684
Stress cardiomyopathy 64.42 52.80 15 506 13340 90614586
Maternal exposure during delivery 57.45 52.80 11 510 3835 90624091

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
Respiratory failure 78.12 68.42 30 264 128102 42492939

FDA Adverse Event Reporting System (Geriatric)

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
Anaphylactic reaction 77.91 49.78 30 803 114270 110474196
Respiratory failure 71.71 49.78 34 799 215298 110373168
Mental status changes postoperative 60.31 49.78 8 825 201 110588265
Confusion postoperative 55.78 49.78 8 825 360 110588106
Stress cardiomyopathy 52.98 49.78 14 819 15792 110572674

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C01CA09 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
CARDIAC STIMULANTS EXCL. CARDIAC GLYCOSIDES
Adrenergic and dopaminergic agents
MeSH PA D000316 Adrenergic alpha-Agonists
MeSH PA D002317 Cardiovascular Agents
MeSH PA D013566 Sympathomimetics
MeSH PA D014662 Vasoconstrictor Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018663 Adrenergic Agents
MeSH PA D058646 Adrenergic alpha-1 Receptor Agonists
CHEBI has role CHEBI:35524 sympathomimetic agent
CHEBI has role CHEBI:35554 cardiovascular drug
CHEBI has role CHEBI:35569 ฮฑ-adrenergic agonist
CHEBI has role CHEBI:50514 vasoconstrictor agent

Related Drugs by ATC class:

C01CA Adrenergic and dopaminergic agents 25 drugs

Drug Use | Suggest Off label Use Form| |View source of the data|

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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
Macrophage migration inhibitory factor Cytokine Ki 4.11 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