Explore a selection of our essential drug information below, or:
Identification
- Summary
Propranolol is a non-selective beta adrenergic antagonist used to treat hypertension, angina, atrial fibrillation, myocardial infarction, migraine, essential tremor, hypertrophic subaortic stenosis, and pheochromocytoma.
- Brand Names
- Hemangeol, Hemangiol, Inderal, Innopran
- Generic Name
- Propranolol
- DrugBank Accession Number
- DB00571
- Background
Propranolol is a racemic mixture of 2 enantiomers where the S(-)-enantiomer has approximately 100 times the binding affinity for beta adrenergic receptors.9 Propranolol is used to treat a number of conditions but most commonly is used for hypertension.8,9,10
Propranolol was granted FDA approval on 13 November 1967.9
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Propranolol (DB00571)
- 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.10,9 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.9,10
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Akathisia caused by antipsychotic use ••• ••••• Management of Angina pectoris •••••••••••• •••••• Management of Angina pectoris •••••••••••• Management of Atrial fibrillation •••••••••••• ••••• ••••••••••• •••••••• Prevention of Cardiovascular mortality •••••••••••• ••••••• •• •• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Propranolol is a beta-adrenergic receptor antagonist used to treat hypertension.9,10 Propranolol has a long duration of action as it is given once or twice daily depending on the indication.8,9,10 When patients abruptly stop taking propranolol, they may experience exacerbations of angina and myocardial infarctions.10
- 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
Target Actions Organism ABeta-1 adrenergic receptor antagonistHumans UBeta-2 adrenergic receptor antagonistHumans UBeta-3 adrenergic receptor antagonistHumans U5-hydroxytryptamine receptor 1A other/unknownHumans U5-hydroxytryptamine receptor 1B other/unknownHumans - 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/kg8,9 or 320L.4
- Protein binding
Approximately 90% of propranolol is protein bound in plasma.8,9,10 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.7 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.10 The plasma half-life of propranolol is 3 to 6 hours.8,9
- 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.8 Propranolol clearance increases linearly with hepatic blood flow.3 Propranolol has a clearance in hypertensive adults of 810mL/min.4
- Adverse Effects
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Symptoms of overdose include hypotension, hypoglycemic seizure, restlessness, euphoria, insomnia.8 Patients with asthma may develop bronchospasm.8 In case of overdose, monitor vital signs, mental status, and blood glucose.8 Treat hypotension with intravenous fluids, bradycardia with atropine, and isoproterenol and aminophylline for bronchospasm.8 If patients do not respond to intravenous fluids, follow up with glucagon 50-150µg/kg intravenously, then 1-5mg/hour, followed by catecholamines.8,9,10 Dialysis will not be useful as propranolol is highly protein bound.8,9,10
- Pathways
Pathway Category Propranolol Action Pathway Drug 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Propranolol may decrease the excretion rate of Abacavir which could result in a higher serum level. Abaloparatide The risk or severity of adverse effects can be increased when Propranolol is combined with Abaloparatide. Abametapir The serum concentration of Propranolol can be increased when it is combined with Abametapir. Abatacept The metabolism of Propranolol can be increased when combined with Abatacept. Abiraterone The serum concentration of Propranolol can be increased when it is combined with Abiraterone. - 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Propranolol hydrochloride F8A3652H1V 318-98-9 ZMRUPTIKESYGQW-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Angilol / Bedranol SR / Cardinol / Ciplar / Deralin / Dociton / Duranol / Indobloc / INNOPRAN / Prophylux / Sumial
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Detensol Tab 10mg Tablet 10 mg Oral Desbergers LtÉe, Division Of Technilab Inc. 1980-12-31 1999-09-17 Canada 
Detensol Tab 120mg Tablet 120 mg Oral Desbergers LtÉe, Division Of Technilab Inc. 1981-12-31 1999-09-17 Canada Detensol Tab 40mg Tablet 40 mg Oral Desbergers LtÉe, Division Of Technilab Inc. 1980-12-31 1999-09-17 Canada Detensol Tab 80mg Tablet 80 mg Oral Desbergers LtÉe, Division Of Technilab Inc. 1980-12-31 1999-09-17 Canada Hemangeol Solution 4.28 mg/1mL Oral Pierre Fabre Pharma S.R.L. 2014-04-14 Not applicable US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-propranolol Tablet 120 mg Oral Apotex Corporation 1981-12-31 Not applicable Canada Apo-propranolol Tablet 40 mg Oral Apotex Corporation 1980-12-31 Not applicable Canada Apo-propranolol Tablet 20 mg Oral Apotex Corporation 1986-12-31 Not applicable Canada Apo-propranolol Tablet 10 mg Oral Apotex Corporation 1980-12-31 Not applicable Canada Apo-propranolol Tablet 80 mg Oral Apotex Corporation 1980-12-31 Not applicable Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image DOCITEREN Propranolol hydrochloride (80 mg/1) + Hydrochlorothiazide (12.5 mg/1) + Triamterene (25 mg/1) Tablet 2006-07-01 Not applicable Germany 
Inderide Propranolol hydrochloride (40 mg/1) + Hydrochlorothiazide (25 mg/1) Tablet Oral Wyeth Pharmaceuticals Inc. 1979-07-01 2008-09-30 US Inderide Propranolol hydrochloride (80 mg/1) + Hydrochlorothiazide (25 mg/1) Tablet Oral Wyeth Pharmaceuticals Inc. 1979-07-01 2008-09-30 US Inderide-40 Tab Propranolol hydrochloride (40 mg) + Hydrochlorothiazide (25 mg) Tablet Oral Wyeth Ayerst Canada Inc. 1993-12-31 2001-06-05 Canada Inderide-80 Tab Propranolol hydrochloride (80 mg) + Hydrochlorothiazide (25 mg) Tablet Oral Wyeth Ayerst Canada Inc. 1993-12-31 2001-05-22 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Propranolol Scopolamine Propranolol hydrochloride (40 mg/40.5mg) + Scopolamine (.5 mg/40.5mg) Tablet Oral TPS 2014-10-01 Not applicable US Propranolol Scopolamine Propranolol hydrochloride (20 mg/20.25mg) + Scopolamine (.25 mg/20.25mg) Tablet Oral TPS 2014-10-01 Not applicable US
Categories
- ATC Codes
- C07FX01 — Propranolol and other combinations
- C07FX — Beta blocking agents, other combinations
- C07F — BETA BLOCKING AGENTS, OTHER COMBINATIONS
- C07 — BETA BLOCKING AGENTS
- C — CARDIOVASCULAR SYSTEM
- C07AA — Beta blocking agents, non-selective
- C07A — BETA BLOCKING AGENTS
- C07 — BETA BLOCKING AGENTS
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic Antagonists
- Adrenergic beta-Antagonists
- Agents causing hyperkalemia
- Alcohols
- Amines
- Amino Alcohols
- Antiarrhythmic agents
- Antihypertensive Agents
- Antihypertensive Agents Indicated for Hypertension
- Beta Blocking Agents and Thiazides
- Beta Blocking Agents, Non-Selective
- Beta Blocking Agents, Non-Selective, and Thiazides
- Bradycardia-Causing Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Hypotensive Agents
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Naphthalenes
- Negative Inotrope
- Neurotransmitter Agents
- OCT2 Inhibitors
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Phenoxypropanolamines
- Propanolamines
- Propanols
- QTc Prolonging Agents
- Vasodilating Agents
- 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)
- Affected organisms
- Humans
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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Routledge PA, Shand DG: Clinical pharmacokinetics of propranolol. Clin Pharmacokinet. 1979 Mar-Apr;4(2):73-90. doi: 10.2165/00003088-197904020-00001. [Article]
- 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. [Article]
- Walle T, Walle K, Mathur RS, Palesch YY, Conradi EC: Propranolol metabolism in normal subjects: association with sex steroid hormones. Clin Pharmacol Ther. 1994 Aug;56(2):127-32. [Article]
- FDA Approved Drug Products: HEMANGEOL (propranolol hydrochloride) oral solution [Link]
- FDA Approved Drug Products: Propranolol Oral Tablet [Link]
- FDA Approved Drug Products: INNOPRAN XL (propranolol hydrochloride) extended release capsules [Link]
- FDA Approved Drug Products: INDERIDE (propranolol hydrochloride and hydrochlorothiazide) tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0001849
- KEGG Drug
- D08443
- KEGG Compound
- C07407
- PubChem Compound
- 4946
- PubChem Substance
- 46505387
- ChemSpider
- 4777
- BindingDB
- 25761
- 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
- FDA label
- Download (256 KB)
- MSDS
- Download (74.7 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Hypertension 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Diagnostic Postural Orthostatic Tachycardia Syndrome (POTS) / Tachycardia 1 somestatus stop reason just information to hide Not Available Completed Not Available Children / Endoscopy / Esophageal Varices in Cirrhosis of the Liver / Upper Gastrointestinal Hemorrhage 1 somestatus stop reason just information to hide Not Available Completed Not Available Coronavirus Disease 2019 (COVID‑19) / COVID / Hypertension 1 somestatus stop reason just information to hide Not Available Completed Not Available Essential Tremor 1 somestatus stop reason just information to hide
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
Form Route Strength Tablet Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 40 mg/1 Tablet, film coated Oral 80 mg/1 Tablet, film coated Oral 80 MG Tablet, film coated Oral Solution Oral 4.28 mg/1mL Solution Oral 3.75 mg / mL Solution Oral 3.75 MG/ML Solution Oral 375.000 mg Injection, solution Intravenous 5 MG/5ML Liquid Intravenous 1 mg / mL Capsule, extended release Oral 120 mg Capsule, extended release Oral 160 mg Capsule, extended release Oral 60 mg Capsule, extended release Oral 80 mg Tablet Oral 10.000 mg Tablet Oral Capsule, extended release Oral 120 mg/1 Capsule, extended release Oral 80 mg/1 Tablet Oral 40.0 mg Tablet Oral Tablet Oral 80 mg Tablet Oral 120 mg Tablet Oral 100 MG Tablet Oral 25 MG Tablet Oral 40.000 mg Injection, solution Intravenous 1 mg/mL Tablet, film coated Oral Capsule, gelatin coated Oral 120 mg/1 Capsule, gelatin coated Oral 160 mg/1 Capsule, gelatin coated Oral 60 mg/1 Capsule, gelatin coated Oral 80 mg/1 Injection Intravenous 1 mg/1mL Injection, solution Intravenous 1 mg/1mL Solution Oral 20 mg/5mL Solution Oral 40 mg/5mL Tablet Oral 10 mg/1 Tablet Oral 20 mg/1 Tablet Oral 40 mg/1 Tablet Oral 50 mg/1 Tablet Oral 60 mg/1 Tablet Oral 80 mg/1 Capsule, extended release Oral 160 mg/1 Capsule, extended release Oral 60 mg/1 Solution Intravenous 1 mg / mL Tablet Oral 10 mg/301 Tablet Oral 20 mg Tablet, film coated Oral 40 mg Tablet Oral 40 mg Tablet Oral 10 mg Tablet, film coated Oral 10 mg Tablet, coated Oral 10 mg Tablet, coated Oral 40 mg - Prices
Unit description Cost Unit Propranolol hcl powder 11.63USD g Propranolol 1 mg/ml vial 10.0USD ml Inderal la 160 mg capsule 8.41USD capsule Inderal LA 160 mg 24 Hour Capsule 7.6USD capsule Inderal la 160 mg capsule sa 7.01USD capsule Inderal la 120 mg capsule 6.42USD capsule Inderal LA 120 mg 24 Hour Capsule 5.8USD capsule Inderal la 120 mg capsule sa 5.36USD capsule Inderal la 80 mg capsule 5.18USD capsule Inderal LA 60 mg 24 Hour Capsule 4.79USD capsule Inderal LA 80 mg 24 Hour Capsule 4.68USD capsule Inderal la 60 mg capsule 4.43USD capsule Inderal la 80 mg capsule sa 4.32USD capsule Inderal la 60 mg capsule sa 3.7USD capsule Propranolol HCl CR 160 mg 24 Hour Capsule 2.62USD capsule InnoPran XL 80 mg 24 Hour Capsule 2.5USD capsule InnoPran XL 120 mg 24 Hour Capsule 2.46USD capsule Innopran xl 120 mg capsule 2.41USD capsule Innopran xl 80 mg capsule 2.41USD capsule Inderide 80-25 mg tablet 2.17USD tablet Propranolol HCl CR 120 mg 24 Hour Capsule 2.0USD capsule Inderide 40-25 mg tablet 1.74USD tablet Propranolol HCl CR 80 mg 24 Hour Capsule 1.61USD capsule Propranolol HCl CR 60 mg 24 Hour Capsule 1.38USD capsule Propranolol HCl 60 mg tablet 1.27USD tablet Inderal-La 160 mg Sustained-Release Capsule 1.26USD capsule Inderal-La 120 mg Sustained-Release Capsule 1.07USD capsule Inderal-La 80 mg Sustained-Release Capsule 0.69USD capsule Propranolol HCl 80 mg tablet 0.66USD tablet Propranolol-HCTZ 80-25 mg tablet 0.65USD tablet Inderal-La 60 mg Sustained-Release Capsule 0.62USD capsule Propranolol-HCTZ 40-25 mg tablet 0.61USD tablet Propranolol 80 mg tablet 0.58USD tablet Propranolol 60 mg tablet 0.56USD tablet Propranolol HCl 40 mg tablet 0.53USD tablet Propranolol 40 mg tablet 0.45USD tablet Propranolol HCl 20 mg tablet 0.36USD tablet Propranolol 20 mg tablet 0.33USD tablet Apo-Propranolol 120 mg Tablet 0.32USD tablet Propranolol HCl 10 mg tablet 0.29USD tablet Propranolol 10 mg tablet 0.22USD tablet Propranolol HCl 20 mg/5ml Solution 0.11USD ml Apo-Propranolol 80 mg Tablet 0.06USD tablet Novo-Pranol 80 mg Tablet 0.06USD tablet Pms-Propranolol 80 mg Tablet 0.06USD tablet Apo-Propranolol 20 mg Tablet 0.04USD tablet Apo-Propranolol 40 mg Tablet 0.04USD tablet Novo-Pranol 20 mg Tablet 0.04USD tablet Novo-Pranol 40 mg Tablet 0.04USD tablet Apo-Propranolol 10 mg Tablet 0.02USD tablet Novo-Pranol 10 mg Tablet 0.02USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6500454 No 2002-12-31 2021-10-04 US US8338489 No 2012-12-25 2028-10-16 US US8987262 No 2015-03-24 2028-10-16 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 96 °C PhysProp water solubility 61.7 mg/L (at 25 °C) MCFARLAND,JW ET AL. (2001) logP 3.48 AVDEEF,A (1997) Caco2 permeability -4.58 ADME Research, USCD pKa 9.42 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0794 mg/mL ALOGPS logP 3.03 ALOGPS logP 2.58 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 14.09 Chemaxon pKa (Strongest Basic) 9.67 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 41.49 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 76.83 m3·mol-1 Chemaxon Polarizability 29.98 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9944 Blood Brain Barrier - 0.9031 Caco-2 permeable + 0.6942 P-glycoprotein substrate Substrate 0.7079 P-glycoprotein inhibitor I Inhibitor 0.5588 P-glycoprotein inhibitor II Non-inhibitor 0.8383 Renal organic cation transporter Non-inhibitor 0.8177 CYP450 2C9 substrate Non-substrate 0.7898 CYP450 2D6 substrate Substrate 0.8918 CYP450 3A4 substrate Non-substrate 0.6463 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.924 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8487 Ames test Non AMES toxic 0.9392 Carcinogenicity Non-carcinogens 0.9097 Biodegradation Not ready biodegradable 0.9871 Rat acute toxicity 2.5625 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9185 hERG inhibition (predictor II) Inhibitor 0.7092
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.4736556 predictedDarkChem Lite v0.1.0 [M-H]- 156.65192 predictedDeepCCS 1.0 (2019) [M+H]+ 172.1881556 predictedDarkChem Lite v0.1.0 [M+H]+ 159.00992 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.1445556 predictedDarkChem Lite v0.1.0 [M+Na]+ 165.10306 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling. Involved in the regulation of sleep/wake behaviors (PubMed:31473062)
- Specific Function
- alpha-2A adrenergic receptor binding
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51222.97 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General 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 30-fold greater affinity than it does norepinephrine
- Specific Function
- adenylate cyclase binding
- Gene Name
- ADRB2
- Uniprot ID
- P07550
- Uniprot Name
- Beta-2 adrenergic receptor
- Molecular Weight
- 46458.32 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General 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
- Specific Function
- beta-3 adrenergic receptor binding
- Gene Name
- ADRB3
- Uniprot ID
- P13945
- Uniprot Name
- Beta-3 adrenergic receptor
- Molecular Weight
- 43518.615 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other/unknown
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:37935376, PubMed:37935377, PubMed:8138923, PubMed:8393041). Also functions as a receptor for various drugs and psychoactive substances (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:38552625, PubMed:8138923, PubMed:8393041). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors, such as adenylate cyclase (PubMed:22957663, PubMed:3138543, PubMed:33762731, PubMed:8138923, PubMed:8393041). HTR1A is coupled to G(i)/G(o) G alpha proteins and mediates inhibitory neurotransmission: signaling inhibits adenylate cyclase activity and activates a phosphatidylinositol-calcium second messenger system that regulates the release of Ca(2+) ions from intracellular stores (PubMed:33762731, PubMed:35610220). Beta-arrestin family members regulate signaling by mediating both receptor desensitization and resensitization processes (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the regulation of 5-hydroxytryptamine release and in the regulation of dopamine and 5-hydroxytryptamine metabolism (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the regulation of dopamine and 5-hydroxytryptamine levels in the brain, and thereby affects neural activity, mood and behavior (PubMed:18476671, PubMed:20363322, PubMed:20945968). Plays a role in the response to anxiogenic stimuli (PubMed:18476671, PubMed:20363322, PubMed:20945968)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other/unknown
- General Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:10452531, PubMed:1315531, PubMed:1328844, PubMed:1348246, PubMed:1351684, PubMed:1559993, PubMed:1565658, PubMed:1610347, PubMed:23519210, PubMed:23519215, PubMed:29925951, PubMed:8218242). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive substances, such as lysergic acid diethylamide (LSD) (PubMed:23519210, PubMed:23519215, PubMed:29925951). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors, such as adenylate cyclase (PubMed:10452531, PubMed:1315531, PubMed:1328844, PubMed:1348246, PubMed:1351684, PubMed:1559993, PubMed:1565658, PubMed:1610347, PubMed:23519210, PubMed:23519215, PubMed:29925951, PubMed:8218242). HTR1B is coupled to G(i)/G(o) G alpha proteins and mediates inhibitory neurotransmission by inhibiting adenylate cyclase activity (PubMed:29925951, PubMed:35610220). Arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:29925951). Regulates the release of 5-hydroxytryptamine, dopamine and acetylcholine in the brain, and thereby affects neural activity, nociceptive processing, pain perception, mood and behavior (PubMed:18476671, PubMed:20945968). Besides, plays a role in vasoconstriction of cerebral arteries (PubMed:15853772)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR1B
- Uniprot ID
- P28222
- Uniprot Name
- 5-hydroxytryptamine receptor 1B
- Molecular Weight
- 43567.535 Da
References
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195)
- Specific Function
- arachidonic acid monooxygenase activity
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Catalyzes the oxidative deamination of primary and some secondary amine such as neurotransmitters, with concomitant reduction of oxygen to hydrogen peroxide and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:18391214, PubMed:20493079, PubMed:24169519, PubMed:8316221). Preferentially oxidizes serotonin (PubMed:20493079, PubMed:24169519). Also catalyzes the oxidative deamination of kynuramine to 3-(2-aminophenyl)-3-oxopropanal that can spontaneously condense to 4-hydroxyquinoline (By similarity)
- Specific Function
- aliphatic amine oxidase activity
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Inderal Monograph [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
References
- 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. [Article]
- Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [Article]
- 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. [Article]
- Carrillo JA, Benitez J: Clinically significant pharmacokinetic interactions between dietary caffeine and medications. Clin Pharmacokinet. 2000 Aug;39(2):127-53. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- Propranolol FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- 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. [Article]
- Goldstein JA: Clinical relevance of genetic polymorphisms in the human CYP2C subfamily. Br J Clin Pharmacol. 2001 Oct;52(4):349-55. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:10681376, PubMed:11093772, PubMed:12865317, PubMed:2732228). Exhibits high catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes 6beta-hydroxylation of the steroid hormones testosterone, progesterone, and androstenedione (PubMed:2732228). Catalyzes the oxidative conversion of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics, including calcium channel blocking drug nifedipine and immunosuppressive drug cyclosporine (PubMed:2732228)
- Specific Function
- aromatase activity
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
- Specific Function
- all-trans retinoic acid 18-hydroxylase activity
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57469.95 Da
References
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- General Function
- Functions as a 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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction
- Specific Function
- Not Available
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23539.43 Da
References
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- 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. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:9260930, PubMed:9687576). Functions as a Na(+)-independent, bidirectional uniporter (PubMed:21128598, PubMed:9687576). Cation cellular uptake or release is driven by the electrochemical potential, i.e. membrane potential and concentration gradient (PubMed:15212162, PubMed:9260930, PubMed:9687576). However, may also engage electroneutral cation exchange when saturating concentrations of cation substrates are reached (By similarity). Predominantly expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (PubMed:15783073). Implicated in monoamine neurotransmitters uptake such as histamine, dopamine, adrenaline/epinephrine, noradrenaline/norepinephrine, serotonin and tyramine, thereby supporting a physiological role in the central nervous system by regulating interstitial concentrations of neurotransmitters (PubMed:16581093, PubMed:17460754, PubMed:9687576). Also capable of transporting dopaminergic neuromodulators cyclo(his-pro), salsolinol and N-methyl-salsolinol, thereby involved in the maintenance of dopaminergic cell integrity in the central nervous system (PubMed:17460754). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Also transports guanidine and endogenous monoamines such as vitamin B1/thiamine, creatinine and N-1-methylnicotinamide (NMN) (PubMed:12089365, PubMed:15212162, PubMed:17072098, PubMed:24961373, PubMed:9260930). Mediates the uptake and efflux of quaternary ammonium compound choline (PubMed:9260930). Mediates the bidirectional transport of polyamine agmatine and the uptake of polyamines putrescine and spermidine (PubMed:12538837, PubMed:21128598). Able to transport non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). Also involved in the uptake of xenobiotic 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:12395288, PubMed:16394027). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- acetylcholine transmembrane transporter activity
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- Molecular Weight
- 141477.255 Da
References
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 11, 2024 18:19