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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:58 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
Data?1582753294
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 practololHMDB
Practolol, eralzdinHMDB
DalzicHMDB
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
Description 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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point134 - 136 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.49 g/LNot Available
LogP0.79HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.0131661259
DarkChem[M-H]-160.0131661259
DeepCCS[M+H]+166.97330932474
DeepCCS[M-H]-164.61530932474
DeepCCS[M-2H]-197.50230932474
DeepCCS[M+Na]+173.06630932474
AllCCS[M+H]+165.432859911
AllCCS[M+H-H2O]+162.232859911
AllCCS[M+NH4]+168.432859911
AllCCS[M+Na]+169.232859911
AllCCS[M-H]-165.832859911
AllCCS[M+Na-2H]-166.532859911
AllCCS[M+HCOO]-167.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PractololCC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C13031.4Standard polar33892256
PractololCC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C12299.9Standard non polar33892256
PractololCC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C12379.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Practolol,1TMS,isomer #1CC(=O)NC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C12470.7Semi standard non polar33892256
Practolol,1TMS,isomer #2CC(=O)NC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C12578.6Semi standard non polar33892256
Practolol,1TMS,isomer #3CC(=O)N(C1=CC=C(OCC(O)CNC(C)C)C=C1)[Si](C)(C)C2278.7Semi standard non polar33892256
Practolol,2TMS,isomer #1CC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C1)[Si](C)(C)C2245.1Semi standard non polar33892256
Practolol,2TMS,isomer #1CC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C1)[Si](C)(C)C2330.6Standard non polar33892256
Practolol,2TMS,isomer #1CC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C)C=C1)[Si](C)(C)C2640.8Standard polar33892256
Practolol,2TMS,isomer #2CC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12632.9Semi standard non polar33892256
Practolol,2TMS,isomer #2CC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12429.1Standard non polar33892256
Practolol,2TMS,isomer #2CC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C12899.7Standard polar33892256
Practolol,2TMS,isomer #3CC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2408.3Semi standard non polar33892256
Practolol,2TMS,isomer #3CC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2456.9Standard non polar33892256
Practolol,2TMS,isomer #3CC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C)C=C1)[Si](C)(C)C2768.0Standard polar33892256
Practolol,3TMS,isomer #1CC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1)[Si](C)(C)C2449.2Semi standard non polar33892256
Practolol,3TMS,isomer #1CC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1)[Si](C)(C)C2446.2Standard non polar33892256
Practolol,3TMS,isomer #1CC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C)O[Si](C)(C)C)C=C1)[Si](C)(C)C2553.0Standard polar33892256
Practolol,1TBDMS,isomer #1CC(=O)NC1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C12723.6Semi standard non polar33892256
Practolol,1TBDMS,isomer #2CC(=O)NC1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C12831.1Semi standard non polar33892256
Practolol,1TBDMS,isomer #3CC(=O)N(C1=CC=C(OCC(O)CNC(C)C)C=C1)[Si](C)(C)C(C)(C)C2513.3Semi standard non polar33892256
Practolol,2TBDMS,isomer #1CC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2680.3Semi standard non polar33892256
Practolol,2TBDMS,isomer #1CC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2765.3Standard non polar33892256
Practolol,2TBDMS,isomer #1CC(=O)N(C1=CC=C(OCC(CNC(C)C)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2838.5Standard polar33892256
Practolol,2TBDMS,isomer #2CC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C13115.8Semi standard non polar33892256
Practolol,2TBDMS,isomer #2CC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C12859.2Standard non polar33892256
Practolol,2TBDMS,isomer #2CC(=O)NC1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C13045.9Standard polar33892256
Practolol,2TBDMS,isomer #3CC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2872.3Semi standard non polar33892256
Practolol,2TBDMS,isomer #3CC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2869.0Standard non polar33892256
Practolol,2TBDMS,isomer #3CC(=O)N(C1=CC=C(OCC(O)CN(C(C)C)[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2933.7Standard polar33892256
Practolol,3TBDMS,isomer #1CC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3121.0Semi standard non polar33892256
Practolol,3TBDMS,isomer #1CC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C3050.2Standard non polar33892256
Practolol,3TBDMS,isomer #1CC(=O)N(C1=CC=C(OCC(CN(C(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C2842.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Practolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zml-9830000000-ea1c4745a41801c725562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Practolol GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9131000000-dcefea3dc328117707fb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Practolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Practolol LC-ESI-qTof , Positive-QTOFsplash10-00dm-3900000000-6e93acc67e2905952d4e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Practolol , positive-QTOFsplash10-00dm-3900000000-6e93acc67e2905952d4e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 10V, Positive-QTOFsplash10-01b9-1290000000-650ef969294a86052e2d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 20V, Positive-QTOFsplash10-00di-6590000000-1d90f501cf7cefbcbf8d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 40V, Positive-QTOFsplash10-05fr-9400000000-bac5f48d64374f54e8ee2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 10V, Negative-QTOFsplash10-014i-2590000000-4cb5d88a3ec166fe39b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 20V, Negative-QTOFsplash10-0zfr-1910000000-1f655397794606d20b8c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 40V, Negative-QTOFsplash10-0a59-2900000000-7641599fadbcb998929f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 10V, Positive-QTOFsplash10-014i-0090000000-cd2fc9bd24e586d509502021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 20V, Positive-QTOFsplash10-014i-3590000000-a6a0c8d9bf31c32a7bdd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 40V, Positive-QTOFsplash10-0ab9-9200000000-9f746c858d33adf0aeb92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 10V, Negative-QTOFsplash10-0gb9-0490000000-8b501e32c9e107a081172021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 20V, Negative-QTOFsplash10-0udi-1900000000-a1c34b11915fee36da722021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Practolol 40V, Negative-QTOFsplash10-053r-1900000000-c13f53a6e1c983e30b552021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01297 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]