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Identification
Name Practolol
Accession Number DB01297
Type small molecule
Groups approved
Description

A beta-adrenergic antagonist that has been used in the emergency treatment of cardiac arrhythmias. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Tocris-0831
Brand names Not Available
Brand name mixtures Not Available
Categories
  • Adrenergic beta-Antagonists
  • Anti-Arrhythmia Agents
CAS number 6673-35-4
Weight Average: 266.3361
Monoisotopic: 266.163042580
Chemical Formula C14H22N2O3
InChI Key InChIKey=DURULFYMVIFBIR-ZDUSSCGKSA-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)/t13-/m0/s1
Plain Text
IUPAC Name
N-{4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}acetamide
SMILES
CC(C)NC[C@H](O)COC1=CC=C(NC(C)=O)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Acetanilides
Substructures
  • Hydroxy Compounds
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Amino Ketones
  • Ethers
  • Benzene and Derivatives
  • Acetanilides
  • Carboxylic Acids and Derivatives
  • Amino Alcohols
  • Aromatic compounds
  • Anisoles
  • Carboxamides and Derivatives
  • Alcohols and Polyols
  • Phenyl Esters
  • Anilines
Pharmacology
Indication Used in the emergency treatment of cardiac arrhythmias.
Pharmacodynamics Practolol 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 action 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Symptoms of overdose include abdominal irritation, central nervous system depression, coma, extremely slow heartbeat, heart failure, lethargy, low blood pressure, and wheezing.
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 134-136 oC
Experimental Properties
Property Value Source
logP 0.79 [HANSCH,C ET AL. (1995)] PhysProp
Caco2 permeability -6.05 [ADME Research, USCD] BiGG
Predicted Properties
Property Value Source
water solubility 4.90e-01 g/l ALOGPS
logP 0.53 ALOGPS
logP 0.83 ChemAxon Molconvert
logS -2.74 ALOGPS
pKa 15.03 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 70.59 ChemAxon Molconvert
rotatable bond count 7 ChemAxon Molconvert
refractivity 75.24 ChemAxon Molconvert
polarizability 30.31 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D05587 Link_out
KEGG Compound C11696 Link_out
PubChem Compound 443371 Link_out
PubChem Substance 46507496 Link_out
ChemSpider 391603 Link_out
ChEBI 258351 Link_out
ChEMBL 258351 Link_out
Therapeutic Targets Database DAP000940 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Practolol Link_out
ATC Codes
  • C07AB01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.
Targets

1. Beta-1 adrenergic receptor

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 30, 2007 08:19 / Updated on April 19, 2011 15:09

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.