Metoprolol

Summary

Metoprolol (CHEMBL13) is an approved small-molecule β-adrenergic antagonist (ATC C07AB02) targeting ADRB1 and ADRB2; indicated across 32 conditions including cardiovascular disorder and atrial fibrillation.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: C07AB02
• Targets: 2 (ADRB1, ADRB2)
• Indications: 32 conditions
• Clinical trials: 138
• Chemistry: 267.36 Da · C15H25NO3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL13
Name	Metoprolol
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	4171
ChEBI	CHEBI:6904
ATC	C07AB02
Molecular formula	C15H25NO3
Molecular weight	267.36
InChIKey	IUBSYMUCCVWXPE-UHFFFAOYSA-N

SMILES: CC(C)NCC(COC1=CC=C(C=C1)CCOC)O

IUPAC name: 1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol

ChEBI definition: A propanolamine that is 1-(propan-2-ylamino)propan-2-ol substituted by a 4-(2-methoxyethyl)phenoxy group at position 1.

Pharmacological roles (ChEBI): β-adrenergic antagonist, antihypertensive agent, geroprotector.

Other ChEBI roles (chemical / environmental): xenobiotic, environmental contaminant.

Also known as: (rs)-metoprolol, Beatrolol, CGP-2175, Dl-metoprolol, H-93/26, Lopressidone, Metoprolol, Metoprolol slow release, Seroken, metoprolol, METOPROLOL, SID251919670

Parent form; salt/anhydrous children: CHEMBL545787, CHEMBL1200337, CHEMBL1200840, CHEMBL2062335, CHEMBL2356097, CHEMBL3989566

Patent coverage: 12,159 distinct patent families (44,342 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
ADRB1	β1-adrenoceptor	Antagonist	7.9	0%	P08588
ADRB2	β2-adrenoceptor	Antagonist	6.9	0.4%	P07550

Broader ChEMBL bioactivity targets: 12 (assay-derived). Sample: Glucocorticoid receptor, Adrenergic receptor beta, Beta-2 adrenergic receptor, Beta-1 adrenergic receptor, Alpha-1A adrenergic receptor, 5-hydroxytryptamine receptor 1A, 3’,5’-cyclic-AMP phosphodiesterase 4D, Cytochrome P450 2D6, Beta-1 adrenergic receptor, Beta-1 adrenergic receptor.

Bioactivity

ChEMBL activities: 26 potent at pChembl ≥ 5 of 30 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ADRB1	7.8	Kd	15.85	nM	CHEMBL_ACT_15644290
P18090	7.64	Kd	22.91	nM	CHEMBL_ACT_1001716
P18090	7.64	Kd	22.91	nM	CHEMBL_ACT_1001720
P18090	7.64	Kd	22.91	nM	CHEMBL_ACT_16742563
P34971	7.31	Ki	49	nM	CHEMBL_ACT_19255943
ADRB1	7.26	Ki	55	nM	CHEMBL_ACT_19255915
ADRB1	6.99	Ki	102	nM	CHEMBL_ACT_7758323
ADRB2	6.89	Kd	130	nM	CHEMBL_ACT_19403983
Q8K4Z4	6.79	Kd	162.2	nM	CHEMBL_ACT_1045646
Q8K4Z4	6.79	Kd	162.2	nM	CHEMBL_ACT_42759
Q8K4Z4	6.79	Kd	162.2	nM	CHEMBL_ACT_534319
ADRB1	6.75	IC50	176	nM	CHEMBL_ACT_7758322
ADRB2	6.66	Ki	220	nM	CHEMBL_ACT_19255927
P18090	6.4	Ki	398.1	nM	CHEMBL_ACT_1720577
P10608	6.3	IC50	500	nM	CHEMBL_ACT_1116437
P18090	6.2	Ki	631	nM	CHEMBL_ACT_1720582
ADRB1	5.82	AC50	1533	nM	CHEMBL_ACT_25121599
ADRB2	5.75	Ki	1769	nM	CHEMBL_ACT_7758325
P18090	5.6	Ki	2512	nM	CHEMBL_ACT_1720578
P18090	5.6	Ki	2512	nM	CHEMBL_ACT_1720583
ADRB2	5.59	IC50	2573	nM	CHEMBL_ACT_7758324
PDE4D	5.36	AC50	4400	nM	CHEMBL_ACT_25185141
CYP2J2	5.31	IC50	4870	nM	CHEMBL_ACT_15461591
P18090	5.3	Ki	5012	nM	CHEMBL_ACT_1720580
ADRB2	5.14	AC50	7250	nM	CHEMBL_ACT_25122732
P19327	5	Ki	10000	nM	CHEMBL_ACT_849639

Target pathways

Aggregated over 2 target gene(s): ADRB1, ADRB2.

Top Reactome pathways

16 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	2	ADRB1, ADRB2
Signaling by GPCR	2	ADRB1, ADRB2
Class A/1 (Rhodopsin-like receptors)	2	ADRB1, ADRB2
Amine ligand-binding receptors	2	ADRB1, ADRB2
GPCR downstream signalling	2	ADRB1, ADRB2
Adrenoceptors	2	ADRB1, ADRB2
G alpha (s) signalling events	2	ADRB1, ADRB2
GPCR ligand binding	2	ADRB1, ADRB2
Membrane Trafficking	1	ADRB2
Metabolism of proteins	1	ADRB2
Vesicle-mediated transport	1	ADRB2
Deubiquitination	1	ADRB2
Ub-specific processing proteases	1	ADRB2
Post-translational protein modification	1	ADRB2
Cargo recognition for clathrin-mediated endocytosis	1	ADRB2
Clathrin-mediated endocytosis	1	ADRB2

Dominant GO biological processes

GO term	Targets
diet induced thermogenesis	2
norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressure	2
adenylate cyclase-activating G protein-coupled receptor signaling pathway	2
response to cold	2
positive regulation of cardiac muscle cell apoptotic process	2
heat generation	2
negative regulation of multicellular organism growth	2
positive regulation of MAPK cascade	2
brown fat cell differentiation	2
adenylate cyclase-activating adrenergic receptor signaling pathway	2
positive regulation of cold-induced thermogenesis	2
signal transduction	2
G protein-coupled receptor signaling pathway	2
positive regulation of heart rate by epinephrine-norepinephrine	1
positive regulation of the force of heart contraction by epinephrine-norepinephrine	1

Indications & clinical

Indications

32 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
atrial fibrillation	3	MONDO:0004981	EFO:0000275
hypertensive disorder	3	MONDO:0005044	EFO:0000537
heart failure	3	MONDO:0005252	EFO:0003144
atherosclerosis	3	MONDO:0005311	EFO:0003914
breast neoplasm	3	MONDO:0021100	MONDO:0007254
congestive heart failure	3	MONDO:0005009	EFO:0000373
coronary artery disorder	3	MONDO:0005010	EFO:0001645
ST-elevation myocardial infarction	3	MONDO:0041656	EFO:0008585
acute myocardial infarction	3	MONDO:0004781	EFO:0008583
myocardial infarction	3	MONDO:0005068	EFO:0000612
type 2 diabetes mellitus	3	MONDO:0005148	MONDO:0005148
acute respiratory distress syndrome	3	MONDO:0006502	EFO:1000637
beta thalassemia	2	MONDO:0019402	Orphanet:848
obesity disorder	2	MONDO:0011122	EFO:0001073
heart disorder	2	MONDO:0005267	EFO:0003777
ventricular fibrillation	2	MONDO:0000190	EFO:0004287
ventricular tachycardia	2	MONDO:0005477	EFO:0005306
Prader-Willi syndrome	2	MONDO:0008300	MONDO:0008300
postural orthostatic tachycardia syndrome	2	MONDO:0011479	EFO:1000645
vascular disorder	2	MONDO:0005385	EFO:0004264
cardiac arrest	2	MONDO:0000745	EFO:0009492
atopic eczema	1	MONDO:0004980	EFO:0000274
neoplasm	1	MONDO:0005070	EFO:0000616
psoriasis	1	MONDO:0005083	EFO:0000676
HIV infectious disease	1	MONDO:0005109	EFO:0000764
Tako-tsubo cardiomyopathy	1	MONDO:0019018	EFO:1002000

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 138.

Phase distribution

Phase	Trials
PHASE4	48
PHASE1	28
Not specified	28
PHASE2	13
PHASE3	10
PHASE2/PHASE3	7
PHASE1/PHASE2	3
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02123056	PHASE4	ACTIVE_NOT_RECRUITING	Assessment of Metoprolol in the Prevention of Vasovagal Syncope in Aging Subjects
NCT03566667	PHASE4	ACTIVE_NOT_RECRUITING	Beta-blockers to Patients With Chronic Obstructive Pulmonary Disease
NCT06569212	PHASE4	RECRUITING	Beta-1 Adrenergic Inhibition to Reduce Cardiac Injury and Inflammation After Subarachnoid Hemorrhage (BADCATS)
NCT06864234	PHASE4	RECRUITING	Effect of Beta-blockers on Coronary Flow and Resistance in Patients With ANOCA
NCT07597564	PHASE4	NOT_YET_RECRUITING	Dose-Response Interaction of Metoprolol and Sufentanil for Attenuating Hemodynamic Responses in Tracheal Intubation
NCT00060918	PHASE4	COMPLETED	Glycemic Control Of Carvedilol Versus Metoprolol In Patients With Type II Diabetes Mellitus And Hypertension
NCT00060931	PHASE4	COMPLETED	Effect Of Carvedilol Versus Metoprolol On Glycemic Control In Patients With Type II Diabetes And Hypertension
NCT00123604	PHASE4	COMPLETED	Vascular Effects of Carvedilol Versus Metoprolol in Hypertensive Patients With Type 2 Diabetes
NCT00222573	PHASE4	COMPLETED	Efficacy and Safety of Adding Clopidogrel to Aspirin or Use of Metoprolol in Myocardial Infarction
NCT00288548	PHASE4	UNKNOWN	Metoprolol and Formoterol in Chronic Obstructive Pulmonary Disease (COPD)
NCT00384566	PHASE4	WITHDRAWN	A Comparison of the Effect of Carvedilol and Metoprolol on Airways Tone in Patients With Heart Failure
NCT00642434	PHASE4	COMPLETED	Comparison of Blood Pressure Medications on Metabolism
NCT00661895	PHASE4	COMPLETED	Black Education and Treatment of Hypertension (BEAT HTN)
NCT00718406	PHASE4	COMPLETED	Pain Relief of Metoprolol Versus Metoprolol Plus Morphine in Acute Chest Pain
NCT00775671	PHASE4	COMPLETED	Comparative Effect of Nebivolol vs. Metoprolol on Insulin Sensitivity and Fibrinolytic Balance in Metabolic Syndrome
NCT00783900	PHASE4	COMPLETED	Intravenous Administration of Metoprolol Versus Biatrial Pacing in the Prevention of Atrial Fibrillation After Cardiac Surgery
NCT00784316	PHASE4	COMPLETED	Intravenous Metoprolol Versus Intravenous Amiodarone in the Prevention of Atrial Fibrillation After Cardiac Surgery
NCT00806390	PHASE4	TERMINATED	Prevention of Anthracycline or Trastuzumab Induced Cardiomyopathy by Metoprolol
NCT00825123	PHASE4	TERMINATED	Effects of Heart Rate Reduction on Central Arterial Pressure in Healthy Individuals
NCT00992056	PHASE4	COMPLETED	Nebivolol Versus Metoprolol: Sodium Sensitivity
NCT00999102	PHASE4	COMPLETED	Nebivolol Versus Metoprolol: Comparative Effects on Fatigue and Quality of Life
NCT01029223	PHASE4	WITHDRAWN	The Influence of Heart Rate Reduction Upon Central Arterial Pressure in Younger and Older Healthy Individuals
NCT01157234	PHASE4	COMPLETED	Nebivolol Effect on Nitric Oxide Levels, Blood Pressure, and Renal Function in Kidney Transplant Patients
NCT01157572	PHASE4	COMPLETED	Effect of Beta Blockade on Left Ventricular Remodeling and Function in Moderate to Severe Asymptomatic Aortic Regurgitation
NCT01203852	PHASE4	COMPLETED	Pharmacogenomic Evaluation of Antihypertensive Responses 2
NCT01395329	PHASE4	COMPLETED	Nebivolol and the Endothelin (ET)-1 System
NCT01404767	PHASE4	TERMINATED	Tight Hemodynamic Control in Patients Who Are Chronically on Metoprolol
NCT01458600	PHASE4	COMPLETED	Adjuvant Treatment of Graves´ Ophthalmopathy With NSAID (aGO Study)
NCT01508325	PHASE4	COMPLETED	Comparison of Bisoprolol With Metoprolol Succinate Sustained-release on Heart Rate and Blood Pressure in Hypertensive Patients
NCT01595516	PHASE4	COMPLETED	Nebivolol and Endothelial Regulation of Fibrinolysis (NERF)
NCT01655303	PHASE4	COMPLETED	Rate Control in Atrial Fibrillation
NCT01755663	PHASE4	UNKNOWN	Comparison of Efficacy of Ivabradine Versus Metoprolol
NCT01837069	PHASE4	TERMINATED	Risk Factor Control Before Orthopedic Surgery
NCT01914926	PHASE4	COMPLETED	Comparison of Diltiazem and Metoprolol in the Management of Acute Atrial Fibrillation or Atrial Flutter
NCT01917149	PHASE4	COMPLETED	Supramaximal Titrated Inhibition of RAAS in Dilated Cardiomyopathy
NCT02025465	PHASE4	UNKNOWN	Randomized Trial Comparing Diltiazem and Metoprolol For Atrial Fibrillation Rate Control
NCT02251509	PHASE4	UNKNOWN	Rate Control in Atrial Fibrillation
NCT02484859	PHASE4	COMPLETED	Comparison of Metoprolol and Tramadol With Remifentanil in Endoscopic Sinus Surgery
NCT02695992	PHASE4	COMPLETED	Rate Control in Atrial Fibrillation II
NCT02746575	PHASE4	COMPLETED	Pilot - Peri-operative Beta Blockade

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (3) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of DPWG Guideline for metoprolol and CYP2D6	DPWG	CYP2D6	yes	yes
Annotation of CPIC Guideline for metoprolol and CYP2D6	CPIC	CYP2D6		yes
Annotation of CPIC Guideline for acebutolol, atenolol, betaxolol, biso	CPIC	ADRA2C;ADRB1;GRK4;GRK5

PharmGKB also curates 17 clinical and 97 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

238 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
Desloratadine	ChEMBL + PubChem	Phase 4 (approved)	ADRB1, ADRB2
Dihydroergotamine	ChEMBL + PubChem	Phase 4 (approved)	ADRB1, ADRB2
OLODATEROL	ChEMBL + PubChem	Phase 4 (approved)	ADRB1, ADRB2
Pramipexole	ChEMBL + PubChem	Phase 4 (approved)	ADRB1, ADRB2
TAMSULOSIN	ChEMBL + PubChem	Phase 4 (approved)	ADRB1, ADRB2
ACEBUTOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
ALBUTEROL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
ARFORMOTEROL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
ATENOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
BENPERIDOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
BETAXOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
BISOPROLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
BROMOCRIPTINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
CANDESARTAN CILEXETIL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
CARTEOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
CARVEDILOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
CELIPROLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
CHLORHEXIDINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
CLEMASTINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
DARIFENACIN	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
DOBUTAMINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
DOMPERIDONE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
EPINEPHRINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
ERGOTAMINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
ESMOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
FENOTEROL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
FLUSPIRILENE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
FORMOTEROL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
INDACATEROL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
ISOPROTERENOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
LABETALOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
LEVOBUNOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
MONTELUKAST	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
NADOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
NEBIVOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
NITAZOXANIDE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
NOREPINEPHRINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
NORTRIPTYLINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
OXPRENOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
PHENYLEPHRINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
PIMOZIDE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
PINDOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
PRACTOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
PRENYLAMINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
PRIMAQUINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
PROPAFENONE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
PROPRANOLOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
RANOLAZINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
RIFAMPIN	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
RIFAXIMIN	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
RITODRINE	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
SALMETEROL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
SOTALOL	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
SUNITINIB	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2
TAMOXIFEN	ChEMBL	Phase 4 (approved)	ADRB1, ADRB2