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Propranolol

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Also known as .beta.-propranololBetalongDl-propranololEuprovasinInderide-40/25Inderide-80/25ProprasylytReducorO-Butyl-hydroxylaminepropanololSID26755283SID90341556SID26751802SID50104497R-PropanololSID124881056Propranol(+/-)-Propranololrac-Propranolol

Summary

Propranolol (CHEMBL27) is an approved small-molecule β-adrenergic antagonist (ATC C07AA05) targeting ADRB2 and ADRB3; indicated across 76 conditions including cardiovascular disorder and portal hypertension.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: C07AA05
  • Targets: 2 (ADRB2, ADRB3)
  • Indications: 76 conditions
  • Clinical trials: 299
  • Chemistry: 259.34 Da · C16H21NO2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL27
NamePropranolol
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID4946
ChEBICHEBI:8499
ATCC07AA05
Molecular formulaC16H21NO2
Molecular weight259.34
InChIKeyAQHHHDLHHXJYJD-UHFFFAOYSA-N

SMILES: CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O

IUPAC name: 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol

ChEBI definition: A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.

Pharmacological roles (ChEBI): β-adrenergic antagonist, anxiolytic drug, anti-arrhythmia drug, vasodilator agent, antihypertensive agent.

Other ChEBI roles (chemical / environmental): xenobiotic, environmental contaminant, human blood serum metabolite.

Also known as: .beta.-propranolol, Betalong, Dl-propranolol, Euprovasin, Inderide-40/25, Inderide-80/25, Propranolol, Proprasylyt, Reducor, O-Butyl-hydroxylamine, propranolol, propanolol

Parent form; salt/anhydrous children: CHEMBL1671

Patent coverage: 23,983 distinct patent families (85,886 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 85,539 (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

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

GeneTargetActionpAffinityCancer dependencyUniProt
ADRB2β2-adrenoceptorAntagonist9.50.4%P07550
ADRB3β3-adrenoceptorAntagonist7.20.1%P13945

Broader ChEMBL bioactivity targets: 37 (assay-derived). Sample: 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, Voltage-dependent L-type calcium channel subunit alpha-1C, Nuclear receptor subfamily 2 group E member 1, Sodium channel protein type 5 subunit alpha, Adrenergic receptor beta, Adrenergic receptor beta, Beta-2 adrenergic receptor, Beta-1 adrenergic receptor.

Bioactivity

ChEMBL activities: 107 potent at pChembl ≥ 5 of 126 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
ADRB210Kd0.1nMCHEMBL_ACT_19403978
ADRB29.62Kd0.24nMCHEMBL_ACT_6360499
ADRB29.49Ki0.32nMCHEMBL_ACT_19255932
ADRB29.34Ki0.46nMCHEMBL_ACT_13871672
ADRB29.32IC500.48nMCHEMBL_ACT_20717206
ADRB29.26IC500.55nMCHEMBL_ACT_20717202
ADRB29.22Kd0.6nMCHEMBL_ACT_6360568
ADRB29.12Ki0.77nMCHEMBL_ACT_7741503
ADRB29.1Kd0.79nMCHEMBL_ACT_2688156
Q8K4Z49.01Kd0.98nMCHEMBL_ACT_1065557
ADRB28.95IC501.12nMCHEMBL_ACT_7741502
Q8K4Z48.9Kd1.26nMCHEMBL_ACT_127932
ADRB28.9Kd1.26nMCHEMBL_ACT_247416
Q8K4Z48.86Kd1.38nMCHEMBL_ACT_14606308
ADRB18.85Ki1.4nMCHEMBL_ACT_19255916
ADRB18.83Ki1.47nMCHEMBL_ACT_7741501
ADRB28.76Ki1.74nMCHEMBL_ACT_18377937
P548338.75Kd1.78nMCHEMBL_ACT_444586
ADRB18.74Kd1.82nMCHEMBL_ACT_6360534
ADRB28.7Kd2nMCHEMBL_ACT_247415
ADRB18.64Ki2.3nMCHEMBL_ACT_114510
P106088.62Ki2.4nMCHEMBL_ACT_127696
P349718.62Ki2.4nMCHEMBL_ACT_19255911
P180908.62Kd2.4nMCHEMBL_ACT_577314
ADRB28.62Kd2.4nMCHEMBL_ACT_87015
ADRB18.6IC502.54nMCHEMBL_ACT_7741500
Q8K4Z48.57Kd2.69nMCHEMBL_ACT_18290263
P180908.52Ki3nMCHEMBL_ACT_12472573
Q8K4Z48.52Kd3.02nMCHEMBL_ACT_530300
P106088.52IC503nMCHEMBL_ACT_577307

Target pathways

Aggregated over 2 target gene(s): ADRB2, ADRB3.

Top Reactome pathways

16 total, by targets touching each:

PathwayTargetsGenes
Signal Transduction2ADRB2, ADRB3
Signaling by GPCR2ADRB2, ADRB3
Class A/1 (Rhodopsin-like receptors)2ADRB2, ADRB3
Amine ligand-binding receptors2ADRB2, ADRB3
GPCR downstream signalling2ADRB2, ADRB3
Adrenoceptors2ADRB2, ADRB3
G alpha (s) signalling events2ADRB2, ADRB3
GPCR ligand binding2ADRB2, ADRB3
Membrane Trafficking1ADRB2
Metabolism of proteins1ADRB2
Vesicle-mediated transport1ADRB2
Deubiquitination1ADRB2
Ub-specific processing proteases1ADRB2
Post-translational protein modification1ADRB2
Cargo recognition for clathrin-mediated endocytosis1ADRB2
Clathrin-mediated endocytosis1ADRB2

Dominant GO biological processes

GO termTargets
diet induced thermogenesis2
norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressure2
adenylate cyclase-modulating G protein-coupled receptor signaling pathway2
response to cold2
heat generation2
negative regulation of multicellular organism growth2
positive regulation of MAPK cascade2
negative regulation of smooth muscle contraction2
brown fat cell differentiation2
adrenergic receptor signaling pathway2
adenylate cyclase-activating adrenergic receptor signaling pathway2
adenylate cyclase-inhibiting adrenergic receptor signaling pathway2
positive regulation of cold-induced thermogenesis2
signal transduction2
G protein-coupled receptor signaling pathway2

Indications & clinical

Indications

76 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).

IndicationTrial phaseMONDOEFO
cardiovascular disorder4MONDO:0004995EFO:0000319
portal hypertension3MONDO:0005080EFO:0000666
post-traumatic stress disorder3MONDO:0005146EFO:0001358
cirrhosis of liver3MONDO:0005155EFO:0001422
colorectal neoplasm3MONDO:0005335EFO:0004142
hemangioma3MONDO:0006500EFO:1000635
myocardial infarction3MONDO:0005068EFO:0000612
ventricular fibrillation3MONDO:0000190EFO:0004287
myocardial ischemia3MONDO:0024644EFO:1001375
esophageal varices3MONDO:0001221EFO:0009545
brain injury3MONDO:0043510MONDO:0043510
migraine disorder3MONDO:0005277MONDO:0005277
hereditary hemorrhagic telangiectasia3MONDO:0019180MONDO:0019180
coronary artery disorder3MONDO:0005010EFO:0001645
heart disorder3MONDO:0005267EFO:0003777
hepatocellular carcinoma2MONDO:0007256EFO:0000182
hypertensive disorder2MONDO:0005044EFO:0000537
injury2MONDO:0021178EFO:0000546
renal cell carcinoma2MONDO:0005086EFO:0000681
stroke disorder2MONDO:0005098EFO:0000712
melanoma2MONDO:0005105EFO:0000756
plasma cell myeloma2MONDO:0009693EFO:0001378
cocaine dependence2MONDO:0005186EFO:0002610
obstructive sleep apnea syndrome2MONDO:0007147EFO:0003918
angiosarcoma2MONDO:0016982EFO:0003968
panic disorder2MONDO:0005383EFO:0004262
anxiety2MONDO:0011918EFO:0005230
orthostatic hypotension2MONDO:0005469EFO:0005252
dystocia2MONDO:0006737EFO:1000911
retinopathy of prematurity2MONDO:0006952EFO:1001158
pancreatic neoplasm2MONDO:0021040EFO:0003860
burn2MONDO:0043519EFO:0009516
gastric neoplasm2MONDO:0021085MONDO:0001056
papilloma2MONDO:0002363MONDO:0002363
substance-related disorder2MONDO:0002494MONDO:0004938
breast neoplasm2MONDO:0021100MONDO:0007254
hypotensive disorder2MONDO:0005468EFO:0005251
age-related macular degeneration2MONDO:0005150EFO:0001365
acute stress disorder2MONDO:0003763EFO:0005223
asthma2MONDO:0004979MONDO:0004979
type 1 diabetes mellitus2MONDO:0005147MONDO:0005147
migraine with aura2MONDO:0005475MONDO:0005475
Marfan syndrome2MONDO:0007947MONDO:0007947
sickle cell disease2MONDO:0011382MONDO:0011382
lymphedema2MONDO:0019297MONDO:0019297
migraine without aura2MONDO:0100431MONDO:0100431
Kaposi’s sarcoma2MONDO:0005055EFO:0000558
triple-negative breast carcinoma2MONDO:0005494EFO:0005537
exocrine pancreatic carcinoma2MONDO:0005192EFO:0002618
anxiety disorder2MONDO:0005618EFO:0006788
chronic obstructive pulmonary disease1MONDO:0005002EFO:0000341
kidney disorder1MONDO:0005240EFO:0003086
fibromyalgia1MONDO:0005546EFO:0005687
postural orthostatic tachycardia syndrome1MONDO:0011479EFO:1000645
major depressive disorder1MONDO:0002009MONDO:0002009
autism spectrum disorder0MONDO:0005258EFO:0003756
osteoporosis0MONDO:0005298EFO:0003882
hypoglycemia0MONDO:0004946HP:0001943
aphasia0MONDO:0000598HP:0002381

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

Clinical trials

Total trials: 299.

Phase distribution

PhaseTrials
PHASE280
PHASE455
Not specified55
PHASE134
PHASE326
PHASE2/PHASE322
EARLY_PHASE118
PHASE1/PHASE29

Top trials by phase / activity

NCTPhaseStatusTitle
NCT05587361PHASE4RECRUITINGBeta-Adrenergic Modulation of Drug Cue Reactivity
NCT05853627PHASE4RECRUITINGMismatch vs. Standard Intervention During Memory Reconsolidation Blockade With Propranolol: Effect on Psychophysiological Reactivity During Traumatic Imagery
NCT05997732PHASE4RECRUITINGSympathetic Neurovascular Transduction: Role of Adrenergic Receptors and Sex Differences
NCT06263452PHASE4RECRUITINGBeta-Blocker Influences on Inflammatory and Neural Responses to Stress
NCT06485726PHASE4RECRUITINGValproate Versus Propranolol in Migraine
NCT06499116PHASE4NOT_YET_RECRUITINGComparison of the Effectiveness of First-line Preventive Treatment of Migraine in Primary Care
NCT06972056PHASE4RECRUITINGComparative Effectiveness of Migraine Preventive Medications: The APT Comparison Study
NCT06982183PHASE4RECRUITINGThe Effects of Propranolol and Hydrocortisone on Military-Relevant Performance Outcomes
NCT07352228PHASE4ENROLLING_BY_INVITATIONCarvedilol vs. Propranolol for Preventing Rebleeding After Endoscopic Treatment of Cirrhotic Varices
NCT07583134PHASE4NOT_YET_RECRUITINGImpact of Propranolol Strategies on Myocardial Injury After Breast Cancer Surgery
NCT00060866PHASE4COMPLETEDPropranolol to Treat Fainting Due to Sympathoadrenal Imbalance
NCT00158262PHASE4COMPLETEDEffect of Propranolol on Preventing Posttraumatic Stress Disorder
NCT00332904PHASE4UNKNOWNEffect of Betablocker or Aldosterone Antagonist Therapy on Patients With Liver Cirrhosis
NCT00645450PHASE4TERMINATEDPTSD Symptom Reduction by Propranolol Given After Trauma Memory Activation
NCT00648375PHASE4TERMINATEDEffectiveness of Propranolol For Treating People With Post-Traumatic Stress Disorder
NCT00709735PHASE4COMPLETEDA Psychophysiologic Study of Weakening Traumatic Combat Memories With Post-Reactivation Propranolol
NCT00862095PHASE4TERMINATEDMedical Therapies for Chronic Post-Traumatic Headaches
NCT00965900PHASE4UNKNOWNEndoscopic Band Ligation (EBL) Versus Propranolol for Primary Prophylaxis of Variceal Bleeding
NCT00966082PHASE4UNKNOWNEBL Versus EBL and Propranolol for the Prevention of Variceal Rebleeding in Pts With Previous Variceal Treatment
NCT00966121PHASE4UNKNOWNEndoscopic Band Ligation (EBL) Versus Endoscopic Band Ligation and Propranolol for the Prevention of Variceal Rebleeding
NCT01059396PHASE4COMPLETEDStudy on B-blockers to Prevent Decompensation of Cirrhosis With HTPortal
NCT01060111PHASE4COMPLETEDAn Efficacy and Tolerability Study of Topiramate in Participants With Migraine
NCT01298271PHASE4UNKNOWNA Randomized Trial of GVS Alone vs. Propranolol
NCT01298284PHASE4UNKNOWNA Trial of EVL\GVS Alone vs. EVL\GVS Combined Propranolol
NCT01451658PHASE4UNKNOWNA Trial of EVL\GVS Alone vs. EVL\GVS Combined Propranolol (S-HCC)
NCT01458600PHASE4COMPLETEDAdjuvant Treatment of Graves´ Ophthalmopathy With NSAID (aGO Study)
NCT01631682PHASE4COMPLETEDPilot Study of Pharmaceutical and Behavioral Interventions to Treat Anxiety Disorders
NCT01655303PHASE4COMPLETEDRate Control in Atrial Fibrillation
NCT01893541PHASE4COMPLETEDPROPRANOLOL PLUS LIGATION REDUCES RECURRENCE OF ESOPHAGEAL VARICES?
NCT01908972PHASE4COMPLETEDThe Safety and Efficiency of Propranolol as an Initial Treatment for Pediatric Hemangioma
NCT01970748PHASE4UNKNOWNPrimary Prevention of Patients With Hepatocellular Carcinoma and Concomitant Esophageal Varices
NCT02032758PHASE4COMPLETEDStudy of Arm and Putter Movement in Golfers With Golfer’s Cramp
NCT02111369PHASE4COMPLETEDPropranolol and Botulinum Toxin for Essential Vocal Tremor
NCT02153944PHASE4COMPLETEDCognitive vs. Emotional Psychopharmacological Manipulations of Fear vs. Anxiety
NCT02171988PHASE4COMPLETEDEffect of Medical Treatment and Prognosis of Postural Orthostatic Tachycardia Syndrome (POTS)
NCT02350985PHASE4COMPLETEDComparison of Propranolol and Venlafaxine in Treatment of Vestibular Migraine
NCT02385422PHASE4UNKNOWNThe Effect of Carvedilol Vs Propranolol in Cirrhotic Patients With Variceal Bleeding
NCT02495883PHASE4COMPLETEDFunctional Imaging of Tremor Circuits and Mechanisms of Treatment Response
NCT02740166PHASE4UNKNOWNPreventing Recurrent Bleeding After Eradication of Esophageal Varices
NCT02790710PHASE4WITHDRAWNBrief Intervention for OCD Fears

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):

GuidelineSourceGene(s)DosingRecommendation
Annotation of CPIC Guideline for acebutolol, betaxolol, bisoprolol, caCPICCYP2D6
Annotation of CPIC Guideline for acebutolol, atenolol, betaxolol, bisoCPICADRA2C;ADRB1;GRK4;GRK5
Annotation of CPIC Guideline for carvedilol, labetalol, nadolol, pindoCPICADRB2

PharmGKB also curates 3 clinical and 15 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

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:

MoleculeSourceStatusShared targets
CLOZAPINEChEMBL + PubChemPhase 4 (approved)ADRB2, ADRB3
CrizotinibChEMBL + PubChemPhase 4 (approved)ADRB2, ADRB3
DESLORATADINEChEMBL + PubChemPhase 4 (approved)ADRB2, ADRB3
DIHYDROERGOTAMINEChEMBL + PubChemPhase 4 (approved)ADRB2, ADRB3
OLANZAPINEChEMBL + PubChemPhase 4 (approved)ADRB2, ADRB3
PRAMIPEXOLEChEMBL + PubChemPhase 4 (approved)ADRB2, ADRB3
RIFAMPINChEMBL + PubChemPhase 4 (approved)ADRB2, ADRB3
TEGASERODChEMBL + PubChemPhase 4 (approved)ADRB2, ADRB3
AMLODIPINEChEMBLPhase 4 (approved)ADRB2, ADRB3
ARIPIPRAZOLEChEMBLPhase 4 (approved)ADRB2, ADRB3
BISOPROLOLChEMBLPhase 4 (approved)ADRB2, ADRB3
BROMOCRIPTINEChEMBLPhase 4 (approved)ADRB2, ADRB3
CARVEDILOLChEMBLPhase 4 (approved)ADRB2, ADRB3
CLOTRIMAZOLEChEMBLPhase 4 (approved)ADRB2, ADRB3
DOXAZOSINChEMBLPhase 4 (approved)ADRB2, ADRB3
EPINEPHRINEChEMBLPhase 4 (approved)ADRB2, ADRB3
FENOTEROLChEMBLPhase 4 (approved)ADRB2, ADRB3
FORMOTEROLChEMBLPhase 4 (approved)ADRB2, ADRB3
HALOPERIDOLChEMBLPhase 4 (approved)ADRB2, ADRB3
ISOPROTERENOLChEMBLPhase 4 (approved)ADRB2, ADRB3
LABETALOLChEMBLPhase 4 (approved)ADRB2, ADRB3
LEVOBUNOLOLChEMBLPhase 4 (approved)ADRB2, ADRB3
MONTELUKASTChEMBLPhase 4 (approved)ADRB2, ADRB3
NOREPINEPHRINEChEMBLPhase 4 (approved)ADRB2, ADRB3
PHENYLEPHRINEChEMBLPhase 4 (approved)ADRB2, ADRB3
PIMOZIDEChEMBLPhase 4 (approved)ADRB2, ADRB3
PINDOLOLChEMBLPhase 4 (approved)ADRB2, ADRB3
PRACTOLOLChEMBLPhase 4 (approved)ADRB2, ADRB3
PROPAFENONEChEMBLPhase 4 (approved)ADRB2, ADRB3
SALMETEROLChEMBLPhase 4 (approved)ADRB2, ADRB3
SOTALOLChEMBLPhase 4 (approved)ADRB2, ADRB3
TAMOXIFENChEMBLPhase 4 (approved)ADRB2, ADRB3
THIORIDAZINEChEMBLPhase 4 (approved)ADRB2, ADRB3
TIMOLOLChEMBLPhase 4 (approved)ADRB2, ADRB3
ALPRENOLOLChEMBLPhase 2ADRB2, ADRB3
BOPINDOLOLChEMBLPhase 2ADRB2, ADRB3
CIMATEROLChEMBLPhase 2ADRB2, ADRB3
FLESTOLOLChEMBLPhase 2ADRB2, ADRB3
LEVISOPRENALINEChEMBLPhase 2ADRB2, ADRB3
LEVOPROPRANOLOLChEMBLPhase 2ADRB2, ADRB3
MILVETEROLChEMBLPhase 2ADRB2, ADRB3
RAFABEGRONChEMBLPhase 2ADRB2, ADRB3
SOLABEGRONChEMBLPhase 2ADRB2, ADRB3
TRETOQUINOLChEMBLPhase 2ADRB2, ADRB3
XAMOTEROLChEMBLPhase 2ADRB2, ADRB3
ZENIDOLOLChEMBLPhase 2ADRB2, ADRB3
AlogliptinPubChemApprovedADRB2, ADRB3
BosentanPubChemApprovedADRB2, ADRB3
FidaxomicinPubChemApprovedADRB2, ADRB3
GlycopyrrolatePubChemApprovedADRB2, ADRB3
LinagliptinPubChemApprovedADRB2, ADRB3
MethotrexatePubChemApprovedADRB2, ADRB3
PropoxyphenePubChemApprovedADRB2, ADRB3
PyrazinamidePubChemApprovedADRB2, ADRB3
SelumetinibPubChemApprovedADRB2, ADRB3
Tiotropium Bromide MonohydratePubChemApprovedADRB2, ADRB3
OLODATEROLChEMBL + PubChemPhase 4 (approved)ADRB2
ACEBUTOLOLChEMBLPhase 4 (approved)ADRB2
ADENOSINEChEMBLPhase 4 (approved)ADRB2
ALBUTEROLChEMBLPhase 4 (approved)ADRB2

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot