Angilol;Apsolol;Avlocardyl;Bedranol;Beprane;Berkolol;Beta-Neg;Beta-Propranolol;Beta-Tablinen;Beta-Timelets;Betachron;Betalong;Cardinol;Caridolol;Corpendol;Deralin;Dociton;Duranol;Efektolol;Elbrol;Etalong;Euprovasin;Frekven;Inderal;Inderal La;Inderide;Indobloc;Innopran XL;Intermigran;Kemi S;Migrastat;Obsidan;Oposim;Prano-Puren;Propanix;Prophylux;Propranolol Hcl Intensol;Propranur;Proprasylyt;Pylapron;Rapynogen;Reducor;Reducor Line;Sagittol;Servanolol;Sloprolol;Sumial;Tesnol;

Dl-Propranolol Hydrochloride;Propanalol;Propanolol;Propranalol;propranolol;Propranolol Hcl;Propranolol Hydrochloride;R,S-Propranolol Hydrochloride;

A widely used non-cardioselective beta-adrenergic antagonist. Propranolol is used in the treatment or prevention of many disorders including acute myocardial infarction, arrhythmias, angina pectoris, hypertension, hypertensive emergencies, hyperthyroidism, migraine, pheochromocytoma, menopause, and anxiety. [PubChem]

• Actavis elizabeth llc
• Akrimax pharmaceuticals llc
• App pharmaceuticals llc
• Baxter healthcare corp anesthesia critical care
• Bedford laboratories div ben venue laboratories inc
• Clonmel healthcare ltd
• Duramed pharmaceuticals inc sub barr laboratories inc
• Glaxosmithkline llc
• Hikma farmaceutica (portugal) sa
• Interpharm inc
• Inwood laboratories inc sub forest laboratories inc
• Ipca laboratories ltd
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Lederle laboratories div american cyanamid co
• Morton grove pharmaceuticals inc
• Mutual pharmaceutical co inc
• Mylan pharmaceuticals inc
• Northstar healthcare holdings ltd
• Par pharmaceutical
• Par pharmaceutical inc
• Pliva inc
• Purepac pharmaceutical co
• Roxane laboratories inc
• Sandoz canada inc
• Sandoz inc
• Schering corp sub schering plough corp
• Smith and nephew solopak div smith and nephew
• Solopak medical products inc
• Superpharm corp
• Teva pharmaceuticals usa inc
• Upsher smith laboratories inc
• Vintage pharmaceuticals
• Warner chilcott div warner lambert co
• Warner chilcott inc
• Watson laboratories inc
• Wyeth ayerst laboratories

• 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

Synthesis Reference

Not Available

General Reference

Brunet A, Orr SP, Tremblay J, Robertson K, Nader K, Pitman RK: Effect of post-retrieval propranolol on psychophysiologic responding during subsequent script-driven traumatic imagery in post-traumatic stress disorder. J Psychiatr Res. 2007 Jun 21;. Pubmed Ohnishi ST, Sadanaga KK, Katsuoka M, Weidanz WP: Effects of membrane acting-drugs on plasmodium species and sickle cell erythrocytes. Mol Cell Biochem. 1989 Nov 23-Dec 19;91(1-2):159-65. Pubmed Singh N, Puri SK: Interaction between chloroquine and diverse pharmacological agents in chloroquine resistant Plasmodium yoelii nigeriensis. Acta Trop. 2000 Nov 2;77(2):185-93. Pubmed Murphy SC, Harrison T, Hamm HE, Lomasney JW, Mohandas N, Haldar K: Erythrocyte G protein as a novel target for malarial chemotherapy. PLoS Med. 2006 Dec;3(12):e528. Pubmed

Type	small molecule

Classes

Naphthalenes

Substructures

Hydroxy Compounds Naphthalenes Aliphatic and Aryl Amines Phenols and Derivatives Ethers Benzene and Derivatives Amino Alcohols Aromatic compounds Anisoles Alcohols and Polyols Phenyl Esters

ANTIHYPERTENSIVES 降血压;

Indication	For the prophylaxis of migraine.
Pharmacodynamics	Propranolol, the prototype of the beta-adrenergic receptor antagonists, is a competitive, nonselective beta-blocker similar to nadolol without intrinsic sympathomimetic activity. Propanolol is a racemic compound; the l-isomer is responsible for adrenergic blocking activity.
Mechanism of action	Propranolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension.
Absorption	Propranolol is almost completely absorbed from the GI tract; however, plasma concentrations attained are quite variable among individuals.
Volume of distribution	4 L
Protein binding	More than 90%
Metabolism	Hepatic Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us. Substrate Enzymes Product Propranolol Cytochrome P450 1A2 N-desisopropylpropranolol Details Propranolol Cytochrome P450 2D6 4'-hydroxypropanolol Details
Route of elimination	Propranolol is extensively metabolized with most metabolites appearing in the urine.
Half life	4 hours
Clearance	Not Available
Toxicity	Symptoms of overdose include bradycardia, cardiac failure, hypotension, and brochospasm. LD50=565 mg/kg (orally in mice).
Affected organisms	Humans and other mammals
Pathways	Pathway Name SMPDB ID Propranolol Pathway SMP00307

Properties
State	solid
Experimental Properties	Property Value Source melting point 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 7.94e-02 g/l 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 ChemAxon rotatable bond count 6 ChemAxon refractivity 76.83 ChemAxon polarizability 29.98 ChemAxon

Drug	Interaction
Acetohexamide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Aminophylline	Antagonism of action and increased effect of theophylline
Bromazepam	Co-administration with propranolol will cause a reduction in bromazepam clearance and increases half-life.
Chlorpromazine	Increased effect of both drugs
Chlorpropamide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Cimetidine	Cimetidine may increase the serum concentration of propranolol by decreasing its metabolism.
Citalopram	The SSRI, citalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
Clonidine	Increased hypertension when clonidine stopped
Dihydroergotamine	Ischemia with risk of gangrene
Dihydroergotoxine	Ischemia with risk of gangrene
Diltiazem	Increased risk of bradycardia
Disopyramide	The beta-blocker, propranolol, may increase the toxicity of disopyramide.
Dronedarone	Propranolol is a CYP2D6 substrate and because dronedarone inhibits this enzyme, will increase propranolol exposure 1.3-fold. Lower dose of metoprolol.
Dyphylline	Antagonism of action and increased effect of theophylline
Epinephrine	Hypertension, then bradycardia
Ergonovine	Ischemia with risk of gangrene
Ergotamine	Ischemia with risk of gangrene
Escitalopram	The SSRI, escitalopram, may increase the bradycardic effect of the beta-blocker, propranolol.
Fenoterol	Antagonism
Fluoxetine	The SSRI, fluoxetine, may increase the bradycardic effect of the beta-blocker, propranolol.
Formoterol	Antagonism
Gliclazide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Glipizide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Glisoxepide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Glyburide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Glycodiazine	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Haloperidol	Increased effect of both drugs
Hydralazine	Increased effect of both drugs
Ibuprofen	Risk of inhibition of renal prostaglandins
Indacaterol	Beta-adrenergic antagonists, especially those that are not cardioselective, may interfere with the effect of indacaterol when administered concurrently. Beta-blockers may exacerbate bronchospasms in patients with COPD.
Indomethacin	Risk of inhibition of renal prostaglandins
Insulin Glargine	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Isoproterenol	Antagonism
Lidocaine	The beta-blocker, propranolol, may increase the effect and toxicity of lidocaine.
Maprotiline	Propranolol increases the serum levels of cisapride
Mesoridazine	Increased risk of cardiotoxicity and arrhythmias
Methyldopa	Possible hypertensive crisis
Methysergide	Ischemia with risk of gangrene
Orciprenaline	Antagonism
Oxtriphylline	Antagonism of action and increased effect of theophylline
Paroxetine	The SSRI, paroxetine, may increase the bradycardic effect of the beta-blocker, propranolol.
Phenobarbital	The barbiturate decreases the effect of the metabolized beta-blocker
Pipobroman	Antagonism
Pirbuterol	Antagonism
Piroxicam	Risk of inhibition of renal prostaglandins
Prazosin	Risk of hypotension at the beginning of therapy
Primidone	The barbiturate decreases the effect of metabolized beta-blocker
Procaterol	Antagonism
Propafenone	Propafenone may increase the effect of the beta-blocker, propranolol.
Repaglinide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Rifampin	Rifampin may decrease the serum concentration of propranolol by increasing its metabolism.
Rizatriptan	Propranolol increases the effect and toxicity of rizatriptan
Salbutamol	Antagonism
Salmeterol	Antagonism
Sertraline	The SSRI, sertraline, may increase the bradycardic effect of the beta-blocker, propranolol.
Terazosin	Increased risk of hypotension. Initiate concomitant therapy cautiously.
Terbinafine	Terbinafine may reduce the metabolism and clearance of Propranolol. Consider alternate therapy or monitor for therapeutic/adverse effects of Propranolol if Terbinafine is initiated, discontinued or dose changed.
Terbutaline	Antagonism
Theophylline	Antagonism of action and increased effect of theophylline
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Tolazamide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Tolbutamide	The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
Topotecan	The p-glycoprotein inhibitor, Propranolol, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
Verapamil	Increased effect of both drugs

• Avoid alcohol.
• Avoid natural licorice.
• Take with food.