You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:18:29 UTC
HMDB IDHMDB0015411
Secondary Accession Numbers
  • HMDB15411
Metabolite Identification
Common NamePractolol
DescriptionPractolol is only found in individuals that have used or taken this drug. It is a beta-adrenergic antagonist that has been used in the emergency treatment of cardiac arrhythmias. [PubChem]Like other beta-adrenergic antagonists, practolol competes with adrenergic neurotransmitters such as catecholamines for binding at sympathetic receptor sites. Like propranolol and timolol, practolol binds at beta(1)-adrenergic receptors in the heart and vascular smooth muscle, inhibiting the effects of the catecholamines epinephrine and norepinephrine and decreasing heart rate, cardiac output, and systolic and diastolic blood pressure.
Structure
Thumb
Synonyms
ValueSource
(+-)-PractololChEBI
1-(4-Acetamidophenoxy)-3-isopropylamino-2-propanolChEBI
4'-(2-Hydroxy-3-(isopropylamino)propoxy)acetanilideChEBI
N-(4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)acetamideChEBI
PractololumChEBI
Tocris-0831HMDB
Eralzdin practololMeSH
Practolol, eralzdinMeSH
DalzicMeSH
Chemical FormulaC14H22N2O3
Average Molecular Weight266.3361
Monoisotopic Molecular Weight266.16304258
IUPAC NameN-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
Traditional Namepractolol
CAS Registry Number6673-35-4
SMILES
CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1
InChI Identifier
InChI=1S/C14H22N2O3/c1-10(2)15-8-13(18)9-19-14-6-4-12(5-7-14)16-11(3)17/h4-7,10,13,15,18H,8-9H2,1-3H3,(H,16,17)
InChI KeyDURULFYMVIFBIR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAcetanilides
Alternative Parents
Substituents
  • Acetanilide
  • N-acetylarylamine
  • Phenoxy compound
  • N-arylamide
  • Phenol ether
  • Alkyl aryl ether
  • Acetamide
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Secondary amine
  • Carboxylic acid derivative
  • Secondary aliphatic amine
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134 - 136 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.49 g/LNot Available
LogP0.79HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.49 g/LALOGPS
logP0.53ALOGPS
logP0.83ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.03ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area70.59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity75.24 m³·mol⁻¹ChemAxon
Polarizability30.39 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zml-9830000000-ea1c4745a41801c72556View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9131000000-dcefea3dc328117707fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00dm-3900000000-6e93acc67e2905952d4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dm-3900000000-6e93acc67e2905952d4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-1290000000-650ef969294a86052e2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-6590000000-1d90f501cf7cefbcbf8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9400000000-bac5f48d64374f54e8eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2590000000-4cb5d88a3ec166fe39b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1910000000-1f655397794606d20b8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-2900000000-7641599fadbcb998929fView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01297 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01297 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01297
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4715
KEGG Compound IDC11696
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPractolol
METLIN IDNot Available
PubChem Compound4883
PDB IDNot Available
ChEBI ID258351
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
References
  1. Abrahamsson T: The beta 1- and beta 2-adrenoceptor stimulatory effects of alprenolol, oxprenolol and pindolol: a study in the isolated right atrium and uterus of the rat. Br J Pharmacol. 1986 Apr;87(4):657-64. [PubMed:2871880 ]
  2. Keyrilainen O, Uusitalo A: A comparative study of three beta 1-adrenoreceptor blocking drugs with different degree of intrinsic stimulating activity (metoprolol, practolol and H 87/07) in patients with angina pectoris. Ann Clin Res. 1978 Aug;10(4):185-90. [PubMed:30388 ]
  3. Saarnivaara L, Lindgren L, Hynynen M: Effects of practolol and metoprolol on QT interval, heart rate and arterial pressure during induction of anaesthesia. Acta Anaesthesiol Scand. 1984 Dec;28(6):644-8. [PubMed:6524278 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]