Identification

Name
Propranolol
Accession Number
DB00571
Description

Propranolol is a racemic mixture of 2 enantiomers where the S(-)-enantiomer has approximately 100 times the binding affinity for beta adrenergic receptors.8 Propranolol is used to treat a number of conditions but most commonly is used for hypertension.7,8,9

Propranolol was granted FDA approval on 13 November 1967.8

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 259.3434
Monoisotopic: 259.157228921
Chemical Formula
C16H21NO2
Synonyms
  • 1-((1-Methylethyl)amino)-3-(1-naphthalenyloxy)-2-propanol
  • 1-(isopropylamino)-3-(1-naphthyloxy)propan-2-ol
  • beta-Propranolol
  • Propanalol
  • Propanolol
  • Propranolol
  • Propranololo
  • Propranololum
  • β-Propranolol
External IDs
  • AY 20694
  • AY-20694

Pharmacology

Indication

Propranolol is indicated to treat hypertension.9,8 Propranolol is also indicated to treat angina pectoris due to coronary atherosclerosis, atrial fibrillation, myocardial infarction, migraine, essential tremor, hypertrophic subaortic stenosis, pheochromocytoma, and proliferating infantile hemangioma.8,9

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Propranolol is a beta-adrenergic receptor antagonist used to treat hypertension8,9. Propranolol has a long duration of action as it is given once or twice daily depending on the indication.7,8,9 When patients abruptly stop taking propranolol, they may experience exacerbations of angina and myocardial infarctions.9

Mechanism of action

Propranolol is a nonselective β-adrenergic receptor antagonist.2 Blocking of these receptors leads to vasoconstriction, inhibition of angiogenic factors like vascular endothelial growth factor (VEGF) and basic growth factor of fibroblasts (bFGF), induction of apoptosis of endothelial cells, as well as down regulation of the renin-angiotensin-aldosterone system.2

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Humans
UBeta-2 adrenergic receptor
antagonist
Humans
UBeta-3 adrenergic receptor
antagonist
Humans
U5-hydroxytryptamine receptor 1A
other/unknown
Humans
U5-hydroxytryptamine receptor 1B
other/unknown
Humans
Absorption

Patients taking doses of 40mg, 80mg, 160mg, and 320mg daily experienced Cmax values of 18±15ng/mL, 52±51ng/mL, 121±98ng/mL, and 245±110ng/mL respectively.4 Propranolol has a Tmax of approximately 2 hours, though this can range from 1 to 4 hours in fasting patients.5 Taking propranolol with food does not increase Tmax but does increase bioavailability.5

Volume of distribution

The volume of distribution of propranolol is approximately 4L/kg7,8 or 320L.4

Protein binding

Approximately 90% of propranolol is protein bound in plasma.7,8,9 Other studies have reported ranges of 85-96%.5

Metabolism

Propranolol undergoes side chain oxidation to α-naphthoxylactic acid, ring oxidation to 4’-hydroxypropranolol, or glucuronidation to propranolol glucuronide.[A36551] It can also be N-desisopropylated to become N-desisopropyl propranolol.1 17% of a dose undergoes glucuronidation and 42% undergoes ring oxidation.6

Hover over products below to view reaction partners

Route of elimination

91% of an oral dose of propranolol is recovered as 12 metabolites in the urine.6

Half-life

The elimination half life of propranolol is approximately 8 hours.9 The plasma half life of propranolol is 3 to 6 hours.7,8

Clearance

The clearance of propranolol is 2.7±0.03L/h/kg in infants <90 days and 3.3±0.35L/h/kg in infants >90 days.7 Propranolol clearance increases linearly with hepatic blood flow.3 Propanolol has a clearance in hypertensive adults of 810mL/min.4

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Symptoms of overdose include hypotension, hypoglycemic seizure, restlessness, euphoria, insomnia.7 Patients with asthma may develop bronchospasm.7 In case of overdose, monitor vital signs, mental status, and blood glucose.7 Treat hypotension with intravenous fluids, bradycardia with atropine, and isoproterenol and aminophylline for bronchospasm.7 If patients do not respond to intravenous fluids, follow up with glucagon 50-150µg/kg intravenously, then 1-5mg/hour, followed by catecholamines.7,8,9 Dialysis will not be useful as propranolol is highly protein bound.7,8,9

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Propranolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirPropranolol may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Propranolol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Propranolol can be increased when combined with Abatacept.
AbirateroneThe serum concentration of Propranolol can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Propranolol can be decreased when combined with Acalabrutinib.
AcarboseThe therapeutic efficacy of Propranolol can be increased when used in combination with Acarbose.
AcebutololPropranolol may increase the arrhythmogenic activities of Acebutolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Propranolol.
AcemetacinAcemetacin may decrease the antihypertensive activities of Propranolol.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Propranolol.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
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Food Interactions
  • Avoid alcohol. Alcohol increases propranolol plasma concentrations.
  • Avoid natural licorice. Natural licorice inhibits the metabolism of propranolol, increasing drug exposure.
  • Take with food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Propranolol hydrochlorideF8A3652H1V318-98-9ZMRUPTIKESYGQW-UHFFFAOYSA-N
Product Images
International/Other Brands
Angilol / Bedranol SR / Cardinol / Ciplar / Deralin / Dociton / Duranol / Indobloc / INNOPRAN / Prophylux / Sumial
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Detensol Tab 10mgTabletOralDesbergers LtÉe, Division Of Technilab Inc.1980-12-311999-09-17Canada flag
Detensol Tab 120mgTabletOralDesbergers LtÉe, Division Of Technilab Inc.1981-12-311999-09-17Canada flag
Detensol Tab 40mgTabletOralDesbergers LtÉe, Division Of Technilab Inc.1980-12-311999-09-17Canada flag
Detensol Tab 80mgTabletOralDesbergers LtÉe, Division Of Technilab Inc.1980-12-311999-09-17Canada flag
HemangeolSolution4.28 mg/1mLOralPierre Fabre Pharmaceuticals, Inc.2014-04-14Not applicableUS flag
HemangiolSolutionOralPierre Fabre Dermo Cosmetique Usa, Inc.2017-03-23Not applicableCanada flag
InderalTablet60 mg/1OralWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.1967-12-012008-10-31US flag
InderalTablet10 mg/1OralWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.1967-12-012008-10-31US flag
InderalTablet40 mg/1OralWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.1967-12-012008-10-31US flag
InderalTablet80 mg/1OralWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.1967-12-012008-10-31US flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo Propranolol Tab 10mgTabletOralApotex Corporation1980-12-31Not applicableCanada flag
Apo Propranolol Tab 120mgTabletOralApotex Corporation1981-12-31Not applicableCanada flag
Apo Propranolol Tab 40mgTabletOralApotex Corporation1980-12-31Not applicableCanada flag
Apo Propranolol Tab 80mgTabletOralApotex Corporation1980-12-31Not applicableCanada flag
Apo-propranolol Tab 20mgTabletOralApotex Corporation1986-12-31Not applicableCanada flag
Dom-propranolol TabletsTabletOralDominion Pharmacal1996-12-312016-10-25Canada flag
Dom-propranolol TabletsTabletOralDominion Pharmacal1996-12-312016-10-25Canada flag
Dom-propranolol Tablets - 80mgTabletOralDominion Pharmacal1996-12-312016-10-25Canada flag
Lupin-propranolol LACapsule, extended releaseOralLupin PharmaNot applicableNot applicableCanada flag
Lupin-propranolol LACapsule, extended releaseOralLupin PharmaNot applicableNot applicableCanada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
InderidePropranolol hydrochloride (40 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralWyeth Pharmaceuticals Inc.1979-07-012008-09-30US flag
InderidePropranolol hydrochloride (80 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralWyeth Pharmaceuticals Inc.1979-07-012008-09-30US flag
Inderide-40 TabPropranolol hydrochloride (40 mg) + Hydrochlorothiazide (25 mg)TabletOralWyeth Ayerst Canada Inc.1993-12-312001-06-05Canada flag
Inderide-80 TabPropranolol hydrochloride (80 mg) + Hydrochlorothiazide (25 mg)TabletOralWyeth Ayerst Canada Inc.1993-12-312001-05-22Canada flag
Propranolol Hydrochloride and HydrochlorothiazidePropranolol hydrochloride (80 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralActavis Pharma Company1990-09-302004-09-30US flag
Propranolol Hydrochloride and HydrochlorothiazidePropranolol hydrochloride (80 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralMylan Pharmaceuticals Inc.1987-04-01Not applicableUS flag
Propranolol Hydrochloride and HydrochlorothiazidePropranolol hydrochloride (40 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralActavis Pharma Company1990-09-302008-09-30US flag
Propranolol Hydrochloride and HydrochlorothiazidePropranolol hydrochloride (40 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralMylan Pharmaceuticals Inc.1987-03-04Not applicableUS flag00378 0731 01 nlmimage10 b60e5b62
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Propranolol ScopolaminePropranolol hydrochloride (40 mg/40.5mg) + Scopolamine (.5 mg/40.5mg)TabletOralTPS2014-10-01Not applicableUS flag
Propranolol ScopolaminePropranolol hydrochloride (20 mg/20.25mg) + Scopolamine (.25 mg/20.25mg)TabletOralTPS2014-10-01Not applicableUS flag

Categories

ATC Codes
C07FX01 — Propranolol and other combinationsC07AA05 — PropranololC07BA05 — Propranolol and thiazides
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Alkyl aryl ethers / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aromatic homopolycyclic compound / Ether / Hydrocarbon derivative / Naphthalene / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
secondary amine, propanolamine, naphthalenes (CHEBI:8499)

Chemical Identifiers

UNII
9Y8NXQ24VQ
CAS number
525-66-6
InChI Key
AQHHHDLHHXJYJD-UHFFFAOYSA-N
InChI
InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3
IUPAC Name
1-(naphthalen-1-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
SMILES
CC(C)NCC(O)COC1=CC=CC2=C1C=CC=C2

References

Synthesis Reference
US3520919
General References
  1. Harrison PM, Tonkin AM, Cahill CM, McLean AJ: Rapid and simultaneous extraction of propranolol, its neutral and basic metabolites from plasma and assay by high-performance liquid chromatography. J Chromatogr. 1985 Oct 11;343(2):349-58. [PubMed:4066876]
  2. Hagen R, Ghareeb E, Jalali O, Zinn Z: Infantile hemangiomas: what have we learned from propranolol? Curr Opin Pediatr. 2018 Aug;30(4):499-504. doi: 10.1097/MOP.0000000000000650. [PubMed:29846253]
  3. Weiss YA, Safar ME, Lehner JP, Levenson JA, Simon A, Alexandre JM: (+)-Propranolol clearance, an estimation of hepatic blood flow in man. Br J Clin Pharmacol. 1978 May;5(5):457-60. doi: 10.1111/j.1365-2125.1978.tb01655.x. [PubMed:656285]
  4. Chidsey CA, Morselli P, Bianchetti G, Morganti A, Leonetti G, Zanchetti A: Studies of the absorption and removal of propranolol in hypertensive patients during therapy. Circulation. 1975 Aug;52(2):313-8. doi: 10.1161/01.cir.52.2.313. [PubMed:1149212]
  5. Routledge PA, Shand DG: Clinical pharmacokinetics of propranolol. Clin Pharmacokinet. 1979 Mar-Apr;4(2):73-90. doi: 10.2165/00003088-197904020-00001. [PubMed:378502]
  6. Walle T, Walle UK, Olanoff LS: Quantitative account of propranolol metabolism in urine of normal man. Drug Metab Dispos. 1985 Mar-Apr;13(2):204-9. [PubMed:2859169]
  7. FDA Approved Drug Products: Propranolol Oral Solution [Link]
  8. FDA Approved Drug Products: Propranolol Oral Tablet [Link]
  9. FDA Approved Drug Products: Propranolol Extended Release Capsule [Link]
Human Metabolome Database
HMDB0001849
KEGG Drug
D08443
KEGG Compound
C07407
PubChem Compound
4946
PubChem Substance
46505387
ChemSpider
4777
BindingDB
25761
RxNav
8787
ChEBI
8499
ChEMBL
CHEMBL27
Therapeutic Targets Database
DAP000089
PharmGKB
PA451145
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Propranolol
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
FDA label
Download (256 KB)
MSDS
Download (74.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableAnxiety Disorders / Post Traumatic Stress Disorder (PTSD)1
4CompletedBasic ScienceCortisol / Inflammatory Reaction / Stress, Psychological / Sympathetic Nervous System1
4CompletedBasic ScienceHyperthyroidism1
4CompletedBasic ScienceSmoking, Cigarette1
4CompletedDiagnosticOccupational; Cramp(s)1
4CompletedPreventionAscites / Hepatic Encephalopathy (HE) / Portal Hypertension Gastropathy / Spontaneous Bacterial Peritonitis (SBP) / Varices, Esophageal1
4CompletedPreventionAtherosclerosis / Cardiovascular Heart Disease / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus / Heart Diseases / High Blood Pressure (Hypertension)1
4CompletedPreventionGraves´ Disease1
4CompletedPreventionLiver Cirrhosis / Varices, Esophageal1
4CompletedPreventionPost Traumatic Stress Disorder (PTSD)1

Pharmacoeconomics

Manufacturers
  • Akrimax pharmaceuticals llc
  • Glaxosmithkline llc
  • Actavis elizabeth llc
  • Inwood laboratories inc sub forest laboratories inc
  • Mylan pharmaceuticals inc
  • Par pharmaceutical
  • Upsher smith laboratories inc
  • Roxane laboratories inc
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hikma farmaceutica (portugal) sa
  • Sandoz canada inc
  • Smith and nephew solopak div smith and nephew
  • Solopak medical products inc
  • Morton grove pharmaceuticals inc
  • Wyeth ayerst laboratories
  • Clonmel healthcare ltd
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Interpharm inc
  • Ipca laboratories ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lederle laboratories div american cyanamid co
  • Mutual pharmaceutical co inc
  • Northstar healthcare holdings ltd
  • Par pharmaceutical inc
  • Pliva inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Schering corp sub schering plough corp
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • Vintage pharmaceuticals
  • Warner chilcott div warner lambert co
  • Warner chilcott inc
  • Watson laboratories inc
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Akrimax Pharmaceuticals
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Barr Pharmaceuticals
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Caremark LLC
  • Comprehensive Consultant Services Inc.
  • Dept Health Central Pharmacy
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Eurand Pharmaceuticals Inc.
  • General Injectables and Vaccines Inc.
  • GlaxoSmithKline Inc.
  • Group Health Cooperative
  • H and H Laboratories
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Heritage Pharmaceuticals
  • Hikma Pharmaceuticals
  • Ipca Laboratories Ltd.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Pharmedix
  • Physicians Total Care Inc.
  • Piramal Healthcare
  • Pliva Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Rouses Point Pharmaceuticals LLC
  • Roxane Labs
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Tya Pharmaceuticals
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Upsher Smith Laboratories
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Wyeth Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet, coatedOral10 mg
Tablet, coatedOral40 mg
TabletOral10 mg
Tablet, coatedOral20 mg
Tablet80 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral80 mg/1
Tablet, film coatedOral80 MG
Tablet, film coatedOral
SolutionOral4.28 mg/1mL
SolutionOral
SolutionOral3.75 MG/ML
Capsule, extended releaseOral160 MG
Capsule, extended releaseOral80 MG
Injection, solutionIntravenous5 MG/5ML
Tablet, film coatedOral40 MG
LiquidIntravenous
Capsule, extended releaseOral
TabletOral
Capsule, extended releaseOral120 mg/1
Capsule, extended releaseOral80 mg/1
TabletOral20 MG
TabletOral100 MG
TabletOral25 MG
TabletOral40 MG
Tablet, coatedOral80 mg
Injection, solutionIntravenous1 mg/mL
Tablet, film coatedOral10 MG
SuspensionOral2 mg/1mL
TabletOral80 mg
Capsule, gelatin coatedOral120 mg/1
Capsule, gelatin coatedOral160 mg/1
Capsule, gelatin coatedOral60 mg/1
Capsule, gelatin coatedOral80 mg/1
InjectionIntravenous1 mg/1mL
Injection, solutionIntravenous1 mg/1mL
SolutionOral20 mg/5mL
SolutionOral40 mg/5mL
TabletOral10 mg/1
TabletOral20 mg/1
TabletOral40 mg/1
TabletOral50 mg/1
TabletOral60 mg/1
TabletOral80 mg/1
Capsule, extended releaseOral160 mg/1
Capsule, extended releaseOral60 mg/1
SolutionIntravenous
TabletOral10 mg/301
Syrup200 mg/100mL
TabletOral
Prices
Unit descriptionCostUnit
Propranolol hcl powder11.63USD g
Propranolol 1 mg/ml vial10.0USD ml
Inderal la 160 mg capsule8.41USD capsule
Inderal LA 160 mg 24 Hour Capsule7.6USD capsule
Inderal la 160 mg capsule sa7.01USD capsule
Inderal la 120 mg capsule6.42USD capsule
Inderal LA 120 mg 24 Hour Capsule5.8USD capsule
Inderal la 120 mg capsule sa5.36USD capsule
Inderal la 80 mg capsule5.18USD capsule
Inderal LA 60 mg 24 Hour Capsule4.79USD capsule
Inderal LA 80 mg 24 Hour Capsule4.68USD capsule
Inderal la 60 mg capsule4.43USD capsule
Inderal la 80 mg capsule sa4.32USD capsule
Inderal la 60 mg capsule sa3.7USD capsule
Propranolol HCl CR 160 mg 24 Hour Capsule2.62USD capsule
InnoPran XL 80 mg 24 Hour Capsule2.5USD capsule
InnoPran XL 120 mg 24 Hour Capsule2.46USD capsule
Innopran xl 120 mg capsule2.41USD capsule
Innopran xl 80 mg capsule2.41USD capsule
Inderide 80-25 mg tablet2.17USD tablet
Propranolol HCl CR 120 mg 24 Hour Capsule2.0USD capsule
Inderide 40-25 mg tablet1.74USD tablet
Propranolol HCl CR 80 mg 24 Hour Capsule1.61USD capsule
Propranolol HCl CR 60 mg 24 Hour Capsule1.38USD capsule
Propranolol HCl 60 mg tablet1.27USD tablet
Inderal-La 160 mg Sustained-Release Capsule1.26USD capsule
Inderal-La 120 mg Sustained-Release Capsule1.07USD capsule
Inderal-La 80 mg Sustained-Release Capsule0.69USD capsule
Propranolol HCl 80 mg tablet0.66USD tablet
Propranolol-HCTZ 80-25 mg tablet0.65USD tablet
Inderal-La 60 mg Sustained-Release Capsule0.62USD capsule
Propranolol-HCTZ 40-25 mg tablet0.61USD tablet
Propranolol 80 mg tablet0.58USD tablet
Propranolol 60 mg tablet0.56USD tablet
Propranolol HCl 40 mg tablet0.53USD tablet
Propranolol 40 mg tablet0.45USD tablet
Propranolol HCl 20 mg tablet0.36USD tablet
Propranolol 20 mg tablet0.33USD tablet
Apo-Propranolol 120 mg Tablet0.32USD tablet
Propranolol HCl 10 mg tablet0.29USD tablet
Propranolol 10 mg tablet0.22USD tablet
Propranolol HCl 20 mg/5ml Solution0.11USD ml
Apo-Propranolol 80 mg Tablet0.06USD tablet
Novo-Pranol 80 mg Tablet0.06USD tablet
Pms-Propranolol 80 mg Tablet0.06USD tablet
Apo-Propranolol 20 mg Tablet0.04USD tablet
Apo-Propranolol 40 mg Tablet0.04USD tablet
Novo-Pranol 20 mg Tablet0.04USD tablet
Novo-Pranol 40 mg Tablet0.04USD tablet
Apo-Propranolol 10 mg Tablet0.02USD tablet
Novo-Pranol 10 mg Tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6500454No2002-12-312021-10-04US flag
US8338489No2012-12-252028-10-16US flag
US8987262No2015-03-242028-10-16US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)96 °CPhysProp
water solubility61.7 mg/L (at 25 °C)MCFARLAND,JW ET AL. (2001)
logP3.48AVDEEF,A (1997)
Caco2 permeability-4.58ADME Research, USCD
pKa9.42SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.0794 mg/mLALOGPS
logP3.03ALOGPS
logP2.58ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.09ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.49 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity76.83 m3·mol-1ChemAxon
Polarizability29.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier-0.9031
Caco-2 permeable+0.6942
P-glycoprotein substrateSubstrate0.7079
P-glycoprotein inhibitor IInhibitor0.5588
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.8177
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.6463
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.924
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8487
Ames testNon AMES toxic0.9392
CarcinogenicityNon-carcinogens0.9097
BiodegradationNot ready biodegradable0.9871
Rat acute toxicity2.5625 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9185
hERG inhibition (predictor II)Inhibitor0.7092
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-03di-0090000000-f8c39664b694f5784865
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-05fr-9000000000-84923a2dc3053801527a
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0fk9-2932000000-fa245a17a643ef33a0b2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-03di-0090000000-ee9d9c871e322202a948
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-03di-0290000000-9f3f72a6b6b792659137
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0avi-5900000000-95293e6a5f843d0cc282
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0ab9-9700000000-6b5b9e9743cb3f7bca58
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0adi-9700000000-f5825268222d45a4ce95
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0159-1900000000-9872255282c6a95633aa
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-00di-9500000000-122203085c028de6cbe4
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0aor-0900000000-39e75b6ae19b4763a0bf
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-004i-0900000000-b75e7bf7aa20ce854157
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-00di-9200000000-2f102916e2fe0f6c1f4b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0c00-9650000000-c4a4f189be72c438d080
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-0910000000-d7db5bab374a7cf02fd3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0090000000-057a63162f5e674c4ce6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0190000000-87c354c205b94f5f06e1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0cl0-4930000000-1eecec66280a12a94b9d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-4900000000-ddd58df17ce1f65a7559
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-4900000000-711c94a7c2e5c24e9e84
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a6r-3900000000-54967b29c739db5eb0d5
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0090000000-057a63162f5e674c4ce6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0190000000-f4e36c8dd4e96992c94d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0830-4920000000-835447ce35e37ab07193
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0ab9-5900000000-25248a6b39724a02096d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-4900000000-5663a764e73595039671
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a6r-3900000000-20d14f48fc5615796a2d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00lr-0910000000-d51a9e2266c2de91bfaa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0090000000-d6c29037a12e6224fc5c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-3590000000-e89d2a443f5d3480df83
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0avi-7900000000-073897b09869caa5bcdc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ab9-7900000000-566e620bc2a178d2a8e7
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ab9-6900000000-21115e5f6c969e2f9e0f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0adi-5900000000-c8d935c939307db2ee51
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0090000000-ee9d9c871e322202a948
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0290000000-53507ada5020c820cd0f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0avi-5900000000-95293e6a5f843d0cc282
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ab9-9700000000-264398d3bc59c8ced5ed
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0adi-9700000000-f5825268222d45a4ce95
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0159-1900000000-63f0b6b57a76617acc2d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-060r-4900000000-c1976ec4cf413372eb24
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-05i0-4900000000-dfc2a11c8d505e07028b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-0900000000-ece05c33751eecfe1c79
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00lr-0900000000-cbbd556232c991733f57
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-4590000000-aaddd1419df983db1236
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Lewis CJ, Gong H, Brown MJ, Harding SE: Overexpression of beta 1-adrenoceptors in adult rat ventricular myocytes enhances CGP 12177A cardiostimulation: implications for 'putative' beta 4-adrenoceptor pharmacology. Br J Pharmacol. 2004 Mar;141(5):813-24. Epub 2004 Feb 2. [PubMed:14757703]
  3. Rouget C, Barthez O, Goirand F, Leroy MJ, Breuiller-Fouche M, Rakotoniaina Z, Guerard P, Morcillo EJ, Advenier C, Sagot P, Cabrol D, Dumas M, Bardou M: Stimulation of the ADRB3 adrenergic receptor induces relaxation of human placental arteries: influence of preeclampsia. Biol Reprod. 2006 Jan;74(1):209-16. Epub 2005 Sep 21. [PubMed:16177222]
  4. Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. [PubMed:17628611]
  5. Rezmann-Vitti LA, Louis SN, Nero TL, Jackman GP, Machida CA, Louis WJ: Site-directed mutagenesis of the rat beta1-adrenoceptor. Involvement of Tyr356 (7.43) in (+/-)cyanopindolol but not (+/-)[125Iodo]cyanopindolol binding. Eur J Med Chem. 2004 Jul;39(7):625-31. [PubMed:15236843]
  6. Yazawa K, Wang JW, Hao LY, Onoue Y, Kameyama M: Verrucotoxin, a stonefish venom, modulates calcium channel activity in guinea-pig ventricular myocytes. Br J Pharmacol. 2007 Aug;151(8):1198-203. Epub 2007 Jun 18. [PubMed:17572694]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Isaza C, Henao J, Ramirez E, Cuesta F, Cacabelos R: Polymorphic variants of the beta2-adrenergic receptor (ADRB2) gene and ADRB2-related propanolol-induced dyslipidemia in the Colombian population. Methods Find Exp Clin Pharmacol. 2005 May;27(4):237-44. [PubMed:16082424]
  2. Rouget C, Barthez O, Goirand F, Leroy MJ, Breuiller-Fouche M, Rakotoniaina Z, Guerard P, Morcillo EJ, Advenier C, Sagot P, Cabrol D, Dumas M, Bardou M: Stimulation of the ADRB3 adrenergic receptor induces relaxation of human placental arteries: influence of preeclampsia. Biol Reprod. 2006 Jan;74(1):209-16. Epub 2005 Sep 21. [PubMed:16177222]
  3. Illingworth CJ, Gooding SR, Winn PJ, Jones GA, Ferenczy GG, Reynolds CA: Classical polarization in hybrid QM/MM methods. J Phys Chem A. 2006 May 25;110(20):6487-97. [PubMed:16706406]
  4. Horinouchi T, Morishima S, Tanaka T, Suzuki F, Tanaka Y, Koike K, Miwa S, Muramatsu I: Different changes of plasma membrane beta-adrenoceptors in rat heart after chronic administration of propranolol, atenolol and bevantolol. Life Sci. 2007 Jul 12;81(5):399-404. Epub 2007 Jun 16. [PubMed:17628611]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name
ADRB3
Uniprot ID
P13945
Uniprot Name
Beta-3 adrenergic receptor
Molecular Weight
43518.615 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Berg T, Piercey BW, Jensen J: Role of beta1-3-adrenoceptors in blood pressure control at rest and during tyramine-induced norepinephrine release in spontaneously hypertensive rats. Hypertension. 2010 May;55(5):1224-30. doi: 10.1161/HYPERTENSIONAHA.109.149286. Epub 2010 Mar 15. [PubMed:20231523]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Smejkal-Jagar L, Boranic M: Serotonin and serotoninergic agents affect proliferation of normal and transformed lymphoid cells. Immunopharmacol Immunotoxicol. 1995 Feb;17(1):151-62. [PubMed:7759768]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Other/unknown
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Bailey SR, Elliott J: Evidence for different 5-HT1B/1D receptors mediating vasoconstriction of equine digital arteries and veins. Eur J Pharmacol. 1998 Aug 21;355(2-3):175-87. [PubMed:9760032]
  2. Choppin A, O'Connor SE: Presence of vasoconstrictor 5HT1-like receptors revealed by precontraction of rabbit isolated mesenteric artery. Br J Pharmacol. 1995 Jan;114(2):309-14. [PubMed:7881730]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Tateishi T, Ohashi K, Fujimura A, Ebihara A: The influence of diltiazem versus cimetidine on propranolol metabolism. J Clin Pharmacol. 1992 Dec;32(12):1099-104. [PubMed:1487547]
  2. Flockhart Table of Drug Interactions [Link]
Details
2. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Yoshimoto K, Echizen H, Chiba K, Tani M, Ishizaki T: Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers--N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol. 1995 Apr;39(4):421-31. [PubMed:7640150]
  2. Lewis DF, Modi S, Dickins M: Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. [PubMed:11996013]
  3. Masubuchi Y, Hosokawa S, Horie T, Suzuki T, Ohmori S, Kitada M, Narimatsu S: Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos. 1994 Nov-Dec;22(6):909-15. [PubMed:7895609]
  4. Rowland K, Yeo WW, Ellis SW, Chadwick IG, Haq I, Lennard MS, Jackson PR, Ramsay LE, Tucker GT: Inhibition of CYP2D6 activity by treatment with propranolol and the role of 4-hydroxy propranolol. Br J Clin Pharmacol. 1994 Jul;38(1):9-14. doi: 10.1111/j.1365-2125.1994.tb04315.x. [PubMed:7946944]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Tateishi T, Ohashi K, Fujimura A, Ebihara A: The influence of diltiazem versus cimetidine on propranolol metabolism. J Clin Pharmacol. 1992 Dec;32(12):1099-104. [PubMed:1487547]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Yoshimoto K, Echizen H, Chiba K, Tani M, Ishizaki T: Identification of human CYP isoforms involved in the metabolism of propranolol enantiomers--N-desisopropylation is mediated mainly by CYP1A2. Br J Clin Pharmacol. 1995 Apr;39(4):421-31. [PubMed:7640150]
  2. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [PubMed:8846619]
  3. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423]
  4. Carrillo JA, Benitez J: Clinically significant pharmacokinetic interactions between dietary caffeine and medications. Clin Pharmacokinet. 2000 Aug;39(2):127-53. [PubMed:10976659]
  5. Masubuchi Y, Hosokawa S, Horie T, Suzuki T, Ohmori S, Kitada M, Narimatsu S: Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos. 1994 Nov-Dec;22(6):909-15. [PubMed:7895609]
  6. McGinnity DF, Parker AJ, Soars M, Riley RJ: Automated definition of the enzymology of drug oxidation by the major human drug metabolizing cytochrome P450s. Drug Metab Dispos. 2000 Nov;28(11):1327-34. [PubMed:11038161]
  7. Usmani KA, Cho TM, Rose RL, Hodgson E: Inhibition of the human liver microsomal and human cytochrome P450 1A2 and 3A4 metabolism of estradiol by deployment-related and other chemicals. Drug Metab Dispos. 2006 Sep;34(9):1606-14. doi: 10.1124/dmd.106.010439. Epub 2006 Jun 21. [PubMed:16790556]
  8. Flockhart Table of Drug Interactions [Link]
  9. Propranolol FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Masubuchi Y, Hosokawa S, Horie T, Suzuki T, Ohmori S, Kitada M, Narimatsu S: Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos. 1994 Nov-Dec;22(6):909-15. [PubMed:7895609]
  2. Goldstein JA: Clinical relevance of genetic polymorphisms in the human CYP2C subfamily. Br J Clin Pharmacol. 2001 Oct;52(4):349-55. [PubMed:11678778]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Tateishi T, Ohashi K, Fujimura A, Ebihara A: The influence of diltiazem versus cimetidine on propranolol metabolism. J Clin Pharmacol. 1992 Dec;32(12):1099-104. [PubMed:1487547]
  2. Masubuchi Y, Hosokawa S, Horie T, Suzuki T, Ohmori S, Kitada M, Narimatsu S: Cytochrome P450 isozymes involved in propranolol metabolism in human liver microsomes. The role of CYP2D6 as ring-hydroxylase and CYP1A2 as N-desisopropylase. Drug Metab Dispos. 1994 Nov-Dec;22(6):909-15. [PubMed:7895609]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Tassaneeyakul W, Birkett DJ, Veronese ME, McManus ME, Tukey RH, Quattrochi LC, Gelboin HV, Miners JO: Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther. 1993 Apr;265(1):401-7. [PubMed:8474022]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Inderal Monograph [File]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Ferry DG, Caplan NB, Cubeddu LX: Interaction between antidepressants and alpha 1-adrenergic receptor antagonists on the binding to alpha 1-acid glycoprotein. J Pharm Sci. 1986 Feb;75(2):146-9. doi: 10.1002/jps.2600750208. [PubMed:2870173]
  2. Miida H, Noritake Y, Shimoda H, Honda K, Matsuoka T, Sakurai K, Shirai M, Manabe S, Takasaki W, Ueno K: Decrease in protein binding and its effect on toxicokinetics (TK)/toxicodynamics (TD) of diclofenac and propranolol in pregnant rats. J Toxicol Sci. 2008 Dec;33(5):525-36. [PubMed:19043274]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Miida H, Noritake Y, Shimoda H, Honda K, Matsuoka T, Sakurai K, Shirai M, Manabe S, Takasaki W, Ueno K: Decrease in protein binding and its effect on toxicokinetics (TK)/toxicodynamics (TD) of diclofenac and propranolol in pregnant rats. J Toxicol Sci. 2008 Dec;33(5):525-36. [PubMed:19043274]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Dudley AJ, Bleasby K, Brown CD: The organic cation transporter OCT2 mediates the uptake of beta-adrenoceptor antagonists across the apical membrane of renal LLC-PK(1) cell monolayers. Br J Pharmacol. 2000 Sep;131(1):71-9. [PubMed:10960071]
Details
2. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103]
  2. D'Emanuele A, Jevprasesphant R, Penny J, Attwood D: The use of a dendrimer-propranolol prodrug to bypass efflux transporters and enhance oral bioavailability. J Control Release. 2004 Mar 24;95(3):447-53. [PubMed:15023456]

Drug created on June 13, 2005 07:24 / Updated on November 25, 2020 15:47

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