Identification

Name
Propranolol
Accession Number
DB00571  (APRD00194)
Type
Small Molecule
Groups
Approved, Investigational
Description

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]

Structure
Thumb
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
Product Ingredients
IngredientUNIICASInChI Key
Propranolol HydrochlorideF8A3652H1V318-98-9ZMRUPTIKESYGQW-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Propranolol Tab 10mgTablet10 mgOralApotex Corporation1980-12-31Not applicableCanada
Apo Propranolol Tab 120mgTablet120 mgOralApotex Corporation1981-12-31Not applicableCanada
Apo Propranolol Tab 40mgTablet40 mgOralApotex Corporation1980-12-31Not applicableCanada
Apo Propranolol Tab 80mgTablet80 mgOralApotex Corporation1980-12-31Not applicableCanada
Detensol Tab 10mgTablet10 mgOralDesbergers LtÉe, Division Of Technilab Inc.1980-12-311999-09-17Canada
Detensol Tab 120mgTablet120 mgOralDesbergers LtÉe, Division Of Technilab Inc.1981-12-311999-09-17Canada
Detensol Tab 40mgTablet40 mgOralDesbergers LtÉe, Division Of Technilab Inc.1980-12-311999-09-17Canada
Detensol Tab 80mgTablet80 mgOralDesbergers LtÉe, Division Of Technilab Inc.1980-12-311999-09-17Canada
HemangeolSolution4.28 mg/1mLOralPierre Fabre Laboratories2014-04-14Not applicableUs
HemangiolSolution3.75 mgOralPierre Fabre Dermo Cosmetique Usa, Inc.2017-03-23Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-propranolol Tab 20mgTablet20 mgOralApotex Corporation1986-12-31Not applicableCanada
Dom-propranolol TabletsTablet10 mgOralDominion Pharmacal1996-12-312016-10-25Canada
Dom-propranolol TabletsTablet40 mgOralDominion Pharmacal1996-12-312016-10-25Canada
Dom-propranolol Tablets - 80mgTablet80 mgOralDominion Pharmacal1996-12-312016-10-25Canada
Novo-pranol Tab 120mgTablet120 mgOralNovopharm Limited1982-12-312005-08-10Canada
Nu-propranolol Tab 10mgTablet10 mgOralNu Pharm Inc1993-12-312012-09-04Canada
Nu-propranolol Tab 120mgTablet120 mgOralNu Pharm Inc1993-12-312012-09-04Canada
Nu-propranolol Tab 20mgTablet20 mgOralNu Pharm Inc1993-12-312012-09-04Canada
Nu-propranolol Tab 40mgTablet40 mgOralNu Pharm Inc1993-12-312012-09-04Canada
Nu-propranolol Tab 80mgTablet80 mgOralNu Pharm Inc1993-12-312012-09-04Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
InderidePropranolol Hydrochloride (80 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralWyeth Pharmaceuticals Inc.1979-07-012008-09-30Us
InderidePropranolol Hydrochloride (40 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralWyeth Pharmaceuticals Inc.1979-07-012008-09-30Us
Inderide-40 TabPropranolol Hydrochloride (40 mg) + Hydrochlorothiazide (25 mg)TabletOralWyeth Ayerst Canada Inc.1993-12-312001-06-05Canada
Inderide-80 TabPropranolol Hydrochloride (80 mg) + Hydrochlorothiazide (25 mg)TabletOralWyeth Ayerst Canada Inc.1993-12-312001-05-22Canada
Propranolol Hydrochloride and HydrochlorothiazidePropranolol Hydrochloride (80 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralMylan Pharmaceuticals1987-04-01Not applicableUs
Propranolol Hydrochloride and HydrochlorothiazidePropranolol Hydrochloride (80 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralActavis Pharma Company1990-09-302004-09-30Us
Propranolol Hydrochloride and HydrochlorothiazidePropranolol Hydrochloride (40 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralMylan Pharmaceuticals1987-03-04Not applicableUs00378 0731 01 nlmimage10 b60e5b62
Propranolol Hydrochloride and HydrochlorothiazidePropranolol Hydrochloride (40 mg/1) + Hydrochlorothiazide (25 mg/1)TabletOralActavis Pharma Company1990-09-302008-09-30Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Propranolol ScopolaminePropranolol Hydrochloride (40 mg/40.5mg) + Scopolamine (.5 mg/40.5mg)TabletOralTPS2014-10-01Not applicableUs
Propranolol ScopolaminePropranolol Hydrochloride (20 mg/20.25mg) + Scopolamine (.25 mg/20.25mg)TabletOralTPS2014-10-01Not applicableUs
International/Other Brands
Angilol / Bedranol SR / Cardinol / Ciplar / Deralin / Dociton / Duranol / Inderal / Indobloc / INNOPRAN / Prophylux / Sumial
Categories
UNII
9Y8NXQ24VQ
CAS number
525-66-6
Weight
Average: 259.3434
Monoisotopic: 259.157228921
Chemical Formula
C16H21NO2
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=CC=CC=C12

Pharmacology

Indication

For the prophylaxis of migraine.

Associated Conditions
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.

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

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
PathwayCategory
Propranolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(1,2,6,7-3H)Testosterone(1,2,6,7-3H)Testosterone may increase the excretion rate of Propranolol which could result in a lower serum level and potentially a reduction in efficacy.
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Propranolol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Propranolol.
1-Testosterone1-Testosterone may increase the excretion rate of Propranolol which could result in a lower serum level and potentially a reduction in efficacy.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Propranolol.
18-methyl-19-nortestosterone18-methyl-19-nortestosterone may increase the excretion rate of Propranolol which could result in a lower serum level and potentially a reduction in efficacy.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Propranolol.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Propranolol.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Propranolol.
4-Hydroxytestosterone4-Hydroxytestosterone may increase the excretion rate of Propranolol which could result in a lower serum level and potentially a reduction in efficacy.
Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.
  • Take with food.

References

Synthesis Reference
US3520919
General References
  1. 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. 2008 May;42(6):503-6. Epub 2007 Jun 22. [PubMed:17588604]
  2. 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:2695829]
  3. 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:11080509]
  4. 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:17194200]
  5. Johnson JA, Herring VL, Wolfe MS, Relling MV: CYP1A2 and CYP2D6 4-hydroxylate propranolol and both reactions exhibit racial differences. J Pharmacol Exp Ther. 2000 Sep;294(3):1099-105. [PubMed:10945865]
External Links
Human Metabolome Database
HMDB0001849
KEGG Compound
C07407
PubChem Compound
4946
PubChem Substance
46505387
ChemSpider
4777
BindingDB
25761
ChEBI
8499
ChEMBL
CHEMBL27
Therapeutic Targets Database
DAP000089
PharmGKB
PA451145
IUPHAR
564
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Propranolol
ATC Codes
C07BA05 — Propranolol and thiazidesC07AA05 — PropranololC07FA05 — Propranolol and other antihypertensives
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
FDA label
Download (256 KB)
MSDS
Download (74.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingBasic ScienceBone, Age-related / Osteoporosis, Age-Related1
0Active Not RecruitingTreatmentPostural Tachycardia Syndrome1
0Not Yet RecruitingTreatmentGastrointestinal Cancers1
0RecruitingBasic ScienceHypoglycemia / Hypoglycemia Unawareness / Type1diabetes1
0RecruitingBasic ScienceMetabolic Syndromes / Normal Body Weight / Obese / Pre-Diabetic1
0RecruitingTreatmentAutism Spectrum Conditions/Disorders1
1Active Not RecruitingBasic ScienceCocaine Dependent Subjects1
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableKidney Diseases1
1CompletedBasic ScienceAmylase / Heart Rate / Memory / Propanolol / Skin Electric Conductance1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Pharmacodynamics of Mirabegron1
1CompletedBasic SciencePulmonary Disease, Chronic Obstructive1
1CompletedDiagnosticHealthy Volunteers1
1CompletedOtherTo Determine Bioequivalence Under Fed Conditions1
1CompletedTreatmentFallopian Tube Cancer / Invasive Epithelial Ovarian Cancer / Primary Peritoneal Carcinoma1
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers / Pulmonary Disease, Chronic Obstructive1
1CompletedTreatmentMajor Depressive Disorder (MDD)1
1CompletedTreatmentProliferative Diabetic Retinopathy (PDR)1
1CompletedTreatmentType 2 Diabetes Mellitus1
1Enrolling by InvitationTreatmentCavernous Malformations,Cerebral and/or Spinal1
1Not Yet RecruitingTreatmentPediatric Cancer1
1TerminatedBasic ScienceDependence, Cocaine1
1TerminatedTreatmentFibromyalgia Pain1
1TerminatedTreatmentSickle Cell Disorders1
1, 2Active Not RecruitingTreatmentChronic Orthostatic Intolerance / Tachycardia1
1, 2CompletedTreatmentRetinopathy of Prematurity1
1, 2Not Yet RecruitingTreatmentHemangiosarcoma1
1, 2RecruitingBasic ScienceCannabis / Post Traumatic Stress Disorder (PTSD)1
1, 2RecruitingTreatmentHemangioma Liver1
1, 2RecruitingTreatmentStage IIIC Cutaneous Melanoma AJCC v7 / Stage IV Cutaneous Melanoma AJCC v6 and v71
1, 2WithdrawnTreatmentDysautonomia / Traumatic Brain Injury (TBI)1
2Active Not RecruitingOtherCancer, Breast / Locally Advanced Malignant Neoplasm1
2Active Not RecruitingSupportive CareMultiple Myeloma (MM)1
2Active Not RecruitingTreatmentDependence, Cocaine1
2CompletedNot AvailableTo Determine Bioequivalence Under Fasting Conditions1
2CompletedTreatmentAlcohol Dependence / Post Traumatic Stress Disorder (PTSD)1
2CompletedTreatmentAsthma Bronchial1
2CompletedTreatmentBrain Injury / Craniocerebral Trauma / Trauma, Nervous System / Traumatic Brain Injury (TBI)1
2CompletedTreatmentCocaine-Related Disorders2
2CompletedTreatmentDependence, Cocaine1
2CompletedTreatmentHealthy Volunteers / Seasonal Affective Disorder (SAD)1
2CompletedTreatmentHemangiomas1
2CompletedTreatmentHyperalgesia1
2CompletedTreatmentInfantile Hemangiomas1
2CompletedTreatmentMinor burns / Pain NOS1
2CompletedTreatmentPhysiology, Ocular / Regional Blood Flow1
2CompletedTreatmentPost Traumatic Stress Disorder (PTSD)1
2CompletedTreatmentRenal Angiomyolipomas / Tuberous Sclerosis1
2CompletedTreatmentSickle Cell Disorders1
2CompletedTreatmentStress Disorders, Traumatic, Acute1
2CompletedTreatmentSyncope1
2CompletedTreatmentTemporomandibular Disorders1
2Enrolling by InvitationTreatmentObstructive Sleep Apnea (OSA)1
2Not Yet RecruitingPreventionRetinopathy of Prematurity1
2Not Yet RecruitingTreatmentAlcohol Drinking1
2Not Yet RecruitingTreatmentMalignant Soft Tissue Sarcoma1
2Not Yet RecruitingTreatmentPanic Disorders1
2Not Yet RecruitingTreatmentRetinopathy of Prematurity1
2RecruitingOtherCerebral Cavernous Malformations1
2RecruitingTreatmentAcute Stress Reaction / Adjustment Disorders / Post Traumatic Stress Disorder (PTSD) / Trauma and Stressor Related Disorders1
2RecruitingTreatmentCerebral Cavernous Malformations1
2RecruitingTreatmentDiabetes, Diabetes Mellitus Type 11
2RecruitingTreatmentInduction of Labor Affected Fetus / Newborn1
2RecruitingTreatmentKaposiform Hemangioendothelioma / Kasabach Merritt Phenomenon1
2RecruitingTreatmentPost Traumatic Stress Disorder (PTSD)1
2RecruitingTreatmentPrimary Lymphedema1
2RecruitingTreatmentProstate Cancer1
2RecruitingTreatmentRecurrent Neuroblastoma1
2SuspendedTreatmentRenal Cell Adenocarcinoma1
2SuspendedTreatmentStage IB Skin Melanoma / Stages II Skin Melanoma / Stages III Skin Melanoma1
2TerminatedTreatmentBack Pain Lower Back1
2TerminatedTreatmentCancer, Breast1
2TerminatedTreatmentDysfunctional Labor1
2TerminatedTreatmentHemangiomas1
2TerminatedTreatmentHemangiomas of Infancy1
2TerminatedTreatmentMetastatic Malignant Melanoma / Unresectable Malignant Melanoma1
2TerminatedTreatmentPosttraumatic Stress Disorders1
2TerminatedTreatmentProstatic Neoplasms1
2TerminatedTreatmentTraumas1
2TerminatedTreatmentTraumatic Brain Injury (TBI)1
2Unknown StatusTreatmentAsthma Bronchial1
2Unknown StatusTreatmentFeeling Anxious1
2Unknown StatusTreatmentPosttraumatic Stress Disorders1
2Unknown StatusTreatmentSubstance Dependence1
2WithdrawnTreatmentTraumas1
2, 3CompletedPreventionHypertension Secondary to Kidney Transplant1
2, 3CompletedPreventionStrokes1
2, 3CompletedTreatmentChronic Migraine / Migraine With Aura / Migraine Without Aura1
2, 3CompletedTreatmentInfantile Hemangiomas1
2, 3CompletedTreatmentRetinopathy of Prematurity1
2, 3CompletedTreatmentMinor burns1
2, 3Not Yet RecruitingTreatmentGastroesophageal variceal hemorrhage prophylaxis / Liver Cirrhosis / Portal Hypertension1
2, 3Not Yet RecruitingTreatmentMelanoma1
2, 3RecruitingTreatmentAdjustment Disorders / Posttraumatic Stress Disorders / Trauma and Stressor Related Disorders1
2, 3RecruitingTreatmentAge Related Macular Degeneration (ARMD)1
2, 3RecruitingTreatmentDental Anxiety1
2, 3RecruitingTreatmentLiver Cirrhosis / Portal Hypertension1
2, 3RecruitingTreatmentTardive Dyskinesia1
2, 3RecruitingTreatmentMinor burns4
2, 3TerminatedTreatmentHemangioma, Capillary1
2, 3WithdrawnTreatmentRecurrent Respiratory Papillomatosis1
3CompletedOtherAnxiety Disorders1
3CompletedPreventionArrythmias / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Death, Sudden,Cardiac / Heart Diseases / Myocardial Infarction / Myocardial Ischemia / Ventricular Fibrillation1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / Myocardial Infarction / Myocardial Ischemia1
3CompletedPreventionChronic Migraine1
3CompletedPreventionLiver Cirrhosis / Portal Hypertension1
3CompletedPreventionNon Cirrhotic Portal Hypertension1
3CompletedTreatmentCessation, Smoking1
3CompletedTreatmentClassic Migraine / Headaches / Migraine Without Aura / Migraines1
3CompletedTreatmentHemangiomas1
3CompletedTreatmentTachycardia, Supraventricular1
3RecruitingTreatmentAscites1
3RecruitingTreatmentGraves Diseases / Hyperthyroidism1
3RecruitingTreatmentInfantile Hemangiomas2
3RecruitingTreatmentLiver Cirrhosis / Oesophageal varices haemorrhage / Portal Vein Thrombosis / Portal Vein, Cavernous Transformation Of1
3RecruitingTreatmentPoor; Labor1
3TerminatedPreventionLiver Cirrhosis / Varices, Esophageal1
3TerminatedTreatmentHemangiomas1
3Unknown StatusPreventionNeoplasms, Colorectal1
3WithdrawnPreventionHemorrhage, Gastrointestinal / Portal Hypertension1
4Active Not RecruitingOtherSocial Anxiety Disorder (SAD)1
4CompletedNot AvailableAnxiety Disorders / Posttraumatic Stress Disorders / Reconsolidation1
4CompletedBasic ScienceCortisol / Inflammatory Reaction / Stress, Psychological / Sympathetic Nervous System1
4CompletedDiagnosticOccupational; Cramp(s)1
4CompletedPreventionAscites / Hepatic Encephalopathy / Portal Hypertension Gastropathy / Spontaneous Bacterial Peritonitis (SBP) / Varices, Esophageal1
4CompletedPreventionGraves´ Disease1
4CompletedPreventionLiver Cirrhosis / Varices, Esophageal1
4CompletedPreventionPost Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentAsthma Bronchial1
4CompletedTreatmentBrain Injuries,Traumatic1
4CompletedTreatmentEssential Vocal Tremor / Essential Voice Tremor / Tremor, Essential / Vocal Tremor / Voice Tremor1
4CompletedTreatmentHemangiomas1
4CompletedTreatmentHyperthyroidism1
4CompletedTreatmentMigrainous Headache1
4CompletedTreatmentNeurocardiogenic Syncope1
4CompletedTreatmentPolycystic Ovaries Syndrome1
4CompletedTreatmentPostural Orthostatic Tachycardia Syndrome (POTS)1
4CompletedTreatmentRapid Ventricular Response Atrial Fibrillation1
4CompletedTreatmentTraumatic Brain Injury (TBI)1
4CompletedTreatmentVestibular Migraine1
4Not Yet RecruitingTreatmentHyperalgesia1
4RecruitingBasic ScienceHyperthyroidism1
4RecruitingBasic ScienceSmoking, Cigarette1
4RecruitingPreventionEsophageal and Gastric Varices / Hemorrhage / Liver Cirrhosis1
4RecruitingPreventionLiver Cirrhosis / Variceal Bleeding1
4RecruitingTreatmentCutaneous calcification1
4RecruitingTreatmentVarices, Esophageal1
4SuspendedOtherObsessive Compulsive Disorder (OCD)1
4TerminatedTreatmentHeadaches1
4TerminatedTreatmentPost Traumatic Stress Disorder (PTSD)1
4TerminatedTreatmentPosttraumatic Stress Disorders1
4Unknown StatusTreatmentBleeding Gastric Varices / Liver Cirrhosis1
4Unknown StatusTreatmentGastroesophageal Varices Hemorrhage / Hepatocellular,Carcinoma1
4Unknown StatusTreatmentHepatocellular,Carcinoma / Liver Cirrhosis1
4Unknown StatusTreatmentHepatocellular,Carcinoma / Oesophageal varices haemorrhage1
4Unknown StatusTreatmentLiver Cirrhosis / Portal Hypertension1
4Unknown StatusTreatmentPost Traumatic Stress Disorder (PTSD)1
Not AvailableActive Not RecruitingNot AvailableTremor, Essential / Tremors1
Not AvailableActive Not RecruitingSupportive CareCervical Cancers1
Not AvailableActive Not RecruitingTreatmentCancer of the Ovary / Fallopian Tube Cancer / Primary Peritoneal Carcinoma1
Not AvailableCompletedNot AvailableHemangiomas1
Not AvailableCompletedNot AvailableHeroin Dependence / Learning and Memory1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedBasic SciencePain Measurement1
Not AvailableCompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Cerebral Arteriosclerosis / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / High Blood Pressure (Hypertension)1
Not AvailableCompletedPreventionLiver Cirrhosis3
Not AvailableCompletedPreventionNonvalvular Atrial Fibrillation1
Not AvailableCompletedPreventionPosttraumatic Stress Disorders1
Not AvailableCompletedTreatmentArrythmias / Nonvalvular Atrial Fibrillation1
Not AvailableRecruitingDiagnosticDecompensated Liver Cirrhosis / Variceal Bleeding1
Not AvailableRecruitingDiagnosticPostural Orthostatic Tachycardia Syndrome (POTS) / Tachycardia1
Not AvailableRecruitingPreventionPost Traumatic Stress Disorder (PTSD)1
Not AvailableRecruitingTreatmentAutism, Early Infantile1
Not AvailableRecruitingTreatmentExtrusion of Tooth1
Not AvailableRecruitingTreatmentGastric Varix / Liver Cirrhoses / Portal Hypertension1
Not AvailableRecruitingTreatmentHepatic Cirrhosis / Liver Cirrhoses1
Not AvailableRecruitingTreatmentHepatocellular,Carcinoma / Male Breast Cancer / Recurrent Melanoma / Stage IV Breast Cancer / Stage IV Melanoma / Stage IV Ovarian Epithelial Cancer / Stage IV Ovarian Germ Cell Tumor / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableRecruitingTreatmentInduction of Labor Affected Fetus / Newborn1
Not AvailableRecruitingTreatmentLiver Cirrhosis / Portal Vein Thrombosis1
Not AvailableRecruitingTreatmentPortal Hypertension2
Not AvailableRecruitingTreatmentPostpartum Haemorrhage (PPH)1
Not AvailableRecruitingTreatmentRetinopathy of Prematurity1
Not AvailableRecruitingTreatmentMinor burns1
Not AvailableUnknown StatusNot AvailableArterial Hypertension / Diabetes Mellitus (DM)1
Not AvailableUnknown StatusBasic ScienceMyofascial Temporomandibular Disorders / Temporomandibular Joint Disorders1
Not AvailableUnknown StatusHealth Services ResearchMigraines1
Not AvailableUnknown StatusPreventionGastric Diseases / Migrainous Headache1
Not AvailableUnknown StatusPreventionPrimary Operable Breast Cancer1
Not AvailableUnknown StatusTreatmentDependence, Cocaine1
Not AvailableUnknown StatusTreatmentPosttraumatic Stress Disorders / Traumatic Memory1
Not AvailableWithdrawnTreatmentAutism, Early Infantile1

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
SolutionOral4.28 mg/1mL
SolutionOral3.75 mg
LiquidIntravenous1 mg
Capsule, extended releaseOral120 mg
Capsule, extended releaseOral160 mg
Capsule, extended releaseOral60 mg
Capsule, extended releaseOral80 mg
TabletOral
Capsule, extended releaseOral120 mg/1
Capsule, extended releaseOral80 mg/1
TabletOral120 mg
Injection, solutionIntravenous1 mg/1mL
Capsule, gelatin coatedOral120 mg/1
Capsule, gelatin coatedOral160 mg/1
Capsule, gelatin coatedOral60 mg/1
Capsule, gelatin coatedOral80 mg/1
InjectionIntravenous1 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
SolutionIntravenous1 mg
TabletOral10 mg/301
TabletOral10 mg
TabletOral20 mg
TabletOral40 mg
TabletOral80 mg
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)
US6500454No2002-12-312021-10-04Us
US8338489No2012-12-252028-10-16Us

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

Taxonomy

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
Naphthalene / Alkyl aryl ether / 1,2-aminoalcohol / Secondary alcohol / Secondary aliphatic amine / Ether / Secondary amine / Organic nitrogen compound / Organonitrogen compound / Organooxygen compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
secondary amine, propanolamine, naphthalenes (CHEBI:8499)

Targets

Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Details
2. Cytochrome P450 2D6
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. 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]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  5. Carrillo JA, Benitez J: Clinically significant pharmacokinetic interactions between dietary caffeine and medications. Clin Pharmacokinet. 2000 Aug;39(2):127-53. [PubMed:10976659]
  6. 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]
  7. 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]
  8. 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]
  9. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  10. Propranolol FDA label [File]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Kind
Protein
Organism
Human
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. [PubMed:2870173]

Transporters

Kind
Protein
Organism
Human
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]
Kind
Protein
Organism
Human
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 20, 2018 13:19