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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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
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
  • N-arylamide
  • Acetanilide
  • Phenol ether
  • Alkyl aryl ether
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • 1,2-aminoalcohol
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
MetabolismNot Available
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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9472
Blood Brain Barrier-0.8609
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.589
P-glycoprotein inhibitor INon-inhibitor0.8705
P-glycoprotein inhibitor IINon-inhibitor0.9147
Renal organic cation transporterNon-inhibitor0.9484
CYP450 2C9 substrateNon-substrate0.781
CYP450 2D6 substrateNon-substrate0.5082
CYP450 3A4 substrateNon-substrate0.6487
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateInhibitor0.6103
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.9289
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9268
Ames testNon AMES toxic0.9153
CarcinogenicityNon-carcinogens0.8402
BiodegradationNot ready biodegradable0.9564
Rat acute toxicity1.9187 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9917
hERG inhibition (predictor II)Non-inhibitor0.898
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 Solubility0.49 mg/mLALOGPS
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesC07AB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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