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Identification
NamePractolol
Accession NumberDB01297
TypeSmall Molecule
GroupsApproved
Description

A beta-adrenergic antagonist that has been used in the emergency treatment of cardiac arrhythmias. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+-)-PractololNot AvailableNot Available
1-(4-Acetamidophenoxy)-3-isopropylamino-2-propanolNot AvailableNot Available
4'-(2-Hydroxy-3-(isopropylamino)propoxy)acetanilideNot AvailableNot Available
N-(4-(2-Hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)acetamideNot AvailableNot Available
PractololumNot AvailableNot Available
Tocris-0831Not AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number6673-35-4
WeightAverage: 266.3361
Monoisotopic: 266.16304258
Chemical FormulaC14H22N2O3
InChI KeyDURULFYMVIFBIR-UHFFFAOYSA-N
InChI
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)
IUPAC Name
N-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
SMILES
CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassAnilides
Direct parentAnilides
Alternative parentsPhenol Ethers; Alkyl Aryl Ethers; Secondary Alcohols; Secondary Carboxylic Acid Amides; 1,2-Aminoalcohols; Dialkylamines; Carboxylic Acids; Polyamines; Enolates
Substituentsphenol ether; alkyl aryl ether; secondary alcohol; secondary carboxylic acid amide; 1,2-aminoalcohol; carboxamide group; polyamine; secondary amine; secondary aliphatic amine; enolate; carboxylic acid derivative; ether; carboxylic acid; amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
Pharmacology
IndicationUsed in the emergency treatment of cardiac arrhythmias.
PharmacodynamicsPractolol is a beta-adrenergic receptor antagonist that has been used in the emergency treatment of cardiac arrhythmias. Beta blockers inhibit normal epinephrine-mediated sympathetic actions, but have minimal effect on resting subjects. That is, they reduce the effect of excitement/physical exertion on heart rate and force of contraction and dilation of blood vessels.
Mechanism of actionLike 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include abdominal irritation, central nervous system depression, coma, extremely slow heartbeat, heart failure, lethargy, low blood pressure, and wheezing.
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Practolol Action PathwayDrug actionSMP00669
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9472
Blood Brain Barrier - 0.8609
Caco-2 permeable - 0.8957
P-glycoprotein substrate Substrate 0.589
P-glycoprotein inhibitor I Non-inhibitor 0.8705
P-glycoprotein inhibitor II Non-inhibitor 0.9147
Renal organic cation transporter Non-inhibitor 0.9484
CYP450 2C9 substrate Non-substrate 0.781
CYP450 2D6 substrate Non-substrate 0.5082
CYP450 3A4 substrate Non-substrate 0.6487
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Inhibitor 0.6103
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.9289
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9268
Ames test Non AMES toxic 0.9153
Carcinogenicity Non-carcinogens 0.8402
Biodegradation Not ready biodegradable 0.9564
Rat acute toxicity 1.9187 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9917
hERG inhibition (predictor II) Non-inhibitor 0.898
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point134-136 °CPhysProp
logP0.79HANSCH,C ET AL. (1995)
Caco2 permeability-6.05ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.49ALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity75.24 m3·mol-1ChemAxon
Polarizability30.39 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD05587
KEGG CompoundC11696
ChEBI258351
ChEMBLCHEMBL6995
Therapeutic Targets DatabaseDAP000940
PharmGKBPA164752820
WikipediaPractolol
ATC CodesC07AB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetohexamideThe beta-blocker, practolol, may decrease symptoms of hypoglycemia.
ChlorpropamideThe beta-blocker, practolol, may decrease symptoms of hypoglycemia.
ClonidineIncreased hypertension when clonidine stopped
DihydroergotamineIschemia with risk of gangrene
DisopyramideThe beta-blocker, practolol, may increase the toxicity of disopyramide.
EpinephrineHypertension, then bradycardia
ErgotamineIschemia with risk of gangrene
FenoterolAntagonism
FormoterolAntagonism
GliclazideThe beta-blocker, practolol, may decrease symptoms of hypoglycemia.
GlyburideThe beta-blocker, practolol, may decrease symptoms of hypoglycemia.
IbuprofenRisk of inhibition of renal prostaglandins
IndomethacinRisk of inhibition of renal prostaglandins
Insulin GlargineThe beta-blocker, practolol, may decrease symptoms of hypoglycemia.
MethysergideIschemia with risk of gangrene
OrciprenalineAntagonism
OxprenololAntagonism
PipobromanAntagonism
PiroxicamRisk of inhibition of renal prostaglandins
PrazosinRisk of hypotension at the beginning of therapy
RepaglinideThe beta-blocker, practolol, may decrease symptoms of hypoglycemia.
TerbutalineAntagonism
Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.

Targets

1. Beta-1 adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details

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
  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
  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
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  5. Buxton IL, Brunton LL: Direct analysis of beta-adrenergic receptor subtypes on intact adult ventricular myocytes of the rat. Circ Res. 1985 Jan;56(1):126-32. Pubmed

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Drug created on June 30, 2007 08:19 / Updated on September 16, 2013 17:14