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Record Information
Version3.6
Creation Date2006-02-16 09:05:30 UTC
Update Date2013-02-09 00:10:51 UTC
HMDB IDHMDB01849
Secondary Accession NumbersNone
Metabolite Identification
Common NamePropranolol
DescriptionPropranolol is 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; Propranolol is a highly lipophilic drug achieving high concentrations in the brain. The duration of action of a single oral dose is longer than the half-life indicates and may be up to 12 hours, if the single dose is high enough (e.g. 80 mg). Effective plasma concentrations are between 10-100 ng/mL. -- Wikipedia; It was the first successful beta blocker developed. Propranolol is commonly marketed by Wyeth under the trade name Inderal.
Structure
Thumb
Synonyms
  1. b-Propranolol
  2. beta-Propranolol
  3. Dociton
  4. Euprovasin
  5. Propanalol
  6. Propanix
  7. Propanolol
  8. Propranololo
Chemical FormulaC16H21NO2
Average Molecular Weight259.3434
Monoisotopic Molecular Weight259.157228921
IUPAC Name[2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine
Traditional Namepropranolol
CAS Registry Number525-66-6
SMILES
CC(C)NCC(O)COC1=CC=CC2=CC=CC=C12
InChI Identifier
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
InChI KeyAQHHHDLHHXJYJD-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassAcenes
Sub ClassNaphthalenes
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • propanolamine(ChEBI)
  • secondary amine(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • Alkyl Aryl Ether
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct ParentNaphthalenes
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point96 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0617 mg/L at 25 °CNot Available
LogP3.48AVDEEF,A (1997)
Predicted Properties
PropertyValueSource
Water Solubility0.079ALOGPS
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
Polarizability29.99 Å3ChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0026 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022707
KNApSAcK IDNot Available
Chemspider ID4777
KEGG Compound IDC07407
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPropranolol
NuGOwiki LinkHMDB01849
Metagene LinkHMDB01849
METLIN ID2170
PubChem Compound4946
PDB IDNot Available
ChEBI ID8499
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Obach RS: Nonspecific binding to microsomes: impact on scale-up of in vitro intrinsic clearance to hepatic clearance as assessed through examination of warfarin, imipramine, and propranolol. Drug Metab Dispos. 1997 Dec;25(12):1359-69. Pubmed: 9394025
  2. Lu C, Li P, Gallegos R, Uttamsingh V, Xia CQ, Miwa GT, Balani SK, Gan LS: Comparison of intrinsic clearance in liver microsomes and hepatocytes from rats and humans: evaluation of free fraction and uptake in hepatocytes. Drug Metab Dispos. 2006 Sep;34(9):1600-5. Epub 2006 Jun 21. Pubmed: 16790553

Enzymes

General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
General function:
Involved in deaminase activity
Specific function:
AMP deaminase plays a critical role in energy metabolism.
Gene Name:
AMPD3
Uniprot ID:
Q01432
Molecular weight:
89727.485
General function:
Involved in deaminase activity
Specific function:
AMP deaminase plays a critical role in energy metabolism.
Gene Name:
AMPD2
Uniprot ID:
Q01433
Molecular weight:
100686.95
General function:
Involved in adenosine kinase activity
Specific function:
ATP dependent phosphorylation of adenosine and other related nucleoside analogs to monophosphate derivatives. Serves as a potential regulator of concentrations of extracellular adenosine and intracellular adenine nucleotides.
Gene Name:
ADK
Uniprot ID:
P55263
Molecular weight:
38702.93
General function:
Involved in deaminase activity
Specific function:
AMP deaminase plays a critical role in energy metabolism.
Gene Name:
AMPD1
Uniprot ID:
P23109
Molecular weight:
90218.455
General function:
Involved in monooxygenase 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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Molecular weight:
43518.6