Metaraminol

Summary

Metaraminol (CHEMBL1201319) is an approved small-molecule α-adrenergic agonist (ATC C01CA09); indicated across 3 conditions including cardiovascular disorder and preeclampsia.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: C01CA09
• Indications: 3 conditions
• Clinical trials: 6
• Chemistry: 167.2 Da · C9H13NO2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1201319
Name	Metaraminol
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	5906
ChEBI	CHEBI:6794
ATC	C01CA09
Molecular formula	C9H13NO2
Molecular weight	167.2
InChIKey	WXFIGDLSSYIKKV-RCOVLWMOSA-N

SMILES: C[C@@H]([C@@H](C1=CC(=CC=C1)O)O)N

IUPAC name: 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol

ChEBI definition: 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.

Pharmacological roles (ChEBI): α-adrenergic agonist, sympathomimetic agent, vasoconstrictor agent.

Also known as: Metaraminol, METARAMINOL, metaraminol, METARAMINOL BITARTRATE

Parent form; salt/anhydrous children: CHEMBL2062262, CHEMBL2062343, CHEMBL3184244, CHEMBL4303541

Patent coverage: 1,078 distinct patent families (3,794 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 3,792 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: 5-hydroxytryptamine receptor 2B, Macrophage migration inhibitory factor, Beta-1 adrenergic receptor, 5-hydroxytryptamine receptor 2A, Alpha-1A adrenergic receptor.

Bioactivity

ChEMBL activities: 1 potent at pChembl ≥ 5 of 7 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
HTR2B	5.13	AC50	7400	nM	CHEMBL_ACT_25227471

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

3 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
cardiovascular disorder	4	MONDO:0004995	EFO:0000319
preeclampsia	3	MONDO:0005081	EFO:0000668
hypotensive disorder	2	MONDO:0005468	EFO:0005251

Clinical trials

Total trials: 6.

Phase distribution

Phase	Trials
PHASE4	2
Not specified	2
PHASE3	1
PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT04991662	PHASE4	COMPLETED	Effect of Three Weight-adjusted Vasopressors for Elective Cesarean Delivery
NCT05084599	PHASE4	COMPLETED	Effect of 90% Effective Dose of Metaraminol in Supine and Left Tilt Positions on Cesarean Section
NCT01451060	PHASE3	WITHDRAWN	Maternal and Neonatal Outcomes of the Use of Vasopressors to Treat Hypotension During Spinal Anesthesia for Cesarean
NCT01108874	PHASE2	COMPLETED	Up-Down Determination of the ED90 of Metaraminol to Treat Hypotension During Cesarean Section
NCT07363109	Not specified	NOT_YET_RECRUITING	Comparison of the Efficacy of Continuous Metaraminol Infusion Versus Continuous Norepinephrine Infusion for the Prevention of Hypotension During Cesarean Section Under Spinal Anaesthesia. A Randomised Controlled Trial.
NCT02245191	Not specified	UNKNOWN	Ephedrine, Phenylephrine and Metaraminol Effects on Maternal Cardiac Output, Uterine Blood Flow and Fetal Circulation

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).