PROPRANOLOL

Search structure
Synonyms:
Status: Approved (1967)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C07AA05
UNII: 9Y8NXQ24VQ

Structure
InChI Key AQHHHDLHHXJYJD-UHFFFAOYSA-N
Smile CC(C)NCC(O)COc1cccc2ccccc12
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H21NO2
Molecular Weight 259.35
AlogP 2.58
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 6.0
Polar Surface Area 41.49
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 19.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 3.48 - EXP
pKa Dissociation Constant 9.42 - EXP
Henry's Law Constant 7.98E-13 atm-m3/mole EST
Atmospheric OH Rate Constant 3.09E-10 cm3/molecule-sec EST
Melting Point 96 deg C EXP
Water Solubility 61.7 mg/L EXP
Vapor Pressure 3.82E-08 mm Hg EST

Pharmacology

Primary Target
β2-adrenoceptor
β3-adrenoceptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 1900-5012 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 2828 - - -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 18000-18000 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 2100 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 1-50 2-253 3-9700 -1-74
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - 12902 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 3981 - 90-113 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 10
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 63200 - - 55
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- - - 48000 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Smoking Cessation 3 D016540 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Esophageal and Gastric Varices 3 D004932 ClinicalTrials
Telangiectasia, Hereditary Hemorrhagic 3 D013683 ClinicalTrials
Tachycardia, Supraventricular 3 D013617 ClinicalTrials
Ventricular Fibrillation 3 D014693 ClinicalTrials
Hemangioma 3 D006391 ClinicalTrials
Migraine Disorders 3 D008881 ClinicalTrials
Ascites 3 D001201 ClinicalTrials
Myocardial Ischemia 3 D017202 ClinicalTrials
Headache 3 D006261 ClinicalTrials
Hypertension, Portal 3 D006975 ClinicalTrials
Myocardial Infarction 3 D009203 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Liver Cirrhosis 3 D008103 ClinicalTrials
Death, Sudden, Cardiac 3 D016757 ClinicalTrials
Migraine without Aura 2 D020326 ClinicalTrials
Dystocia 2 D004420 ClinicalTrials
Retinopathy of Prematurity 2 D012178 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Marfan Syndrome 2 D008382 ClinicalTrials
Lymphedema 2 D008209 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Asthma 2 D001249 ClinicalTrials
Hypertension 2 D006973 ClinicalTrials
Wounds and Injuries 2 D014947 ClinicalTrials
Carcinoma, Hepatocellular 2 D006528 ClinicalTrials
Stroke 2 D020521 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Stress Disorders, Post-Traumatic 2 D013313 ClinicalTrials
Diabetes Mellitus, Type 1 2 D003922 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Pain 2 D010146 ClinicalTrials
Sleep Apnea, Obstructive 2 D020181 ClinicalTrials
Hemangiosarcoma 2 D006394 ClinicalTrials
Panic Disorder 2 D016584 ClinicalTrials
Hypotension, Orthostatic 2 D007024 ClinicalTrials
Migraine with Aura 2 D020325 ClinicalTrials
Burns 2 D002056 ClinicalTrials
Syncope 2 D013575 ClinicalTrials
Shoulder Pain 2 D020069 ClinicalTrials
Low Back Pain 2 D017116 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Papilloma 2 D010212 ClinicalTrials
Substance-Related Disorders 2 D019966 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Brain Injuries 2 D001930 ClinicalTrials
Hypotension 2 D007022 ClinicalTrials
Alcohol Drinking 2 D000428 ClinicalTrials
Kidney Diseases 1 D007674 ClinicalTrials
Memory Disorders 1 D008569 ClinicalTrials
Hemangioma, Cavernous, Central Nervous System 1 D020786 ClinicalTrials
Orthostatic Intolerance 1 D054971 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 1 D029424 ClinicalTrials
Depressive Disorder, Major 1 D003865 ClinicalTrials
Fibromyalgia 1 D005356 ClinicalTrials
Osteoporosis 0 D010024 ClinicalTrials
Child Development Disorders, Pervasive 0 D002659 ClinicalTrials
Hypoglycemia 0 D007003 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 525-66-6
ChEBI 8499
ChEMBL CHEMBL27
DrugBank DB00571
DrugCentral 2303
EPA CompTox DTXSID6023525
FDA SRS 9Y8NXQ24VQ
Human Metabolome Database HMDB0001849
Guide to Pharmacology 564
KEGG C07407
PharmGKB PA451145
PubChem 4946
SureChEMBL SCHEMBL3955
CONTENTS