DrugBank: Practolol (DB01297)

targets (1)

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Tocris-0831

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Adrenergic beta-Antagonists
Anti-Arrhythmia Agents

CAS number

6673-35-4

Weight

Average: 266.3361
Monoisotopic: 266.16304258

Chemical Formula

C₁₄H₂₂N₂O₃

InChI Key

InChIKey=DURULFYMVIFBIR-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)

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

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

Not Available

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

Experimental Properties

Property	Value	Source
melting point	134-136 °C	PhysProp
logP	0.79	HANSCH,C ET AL. (1995)
Caco2 permeability	-6.05	ADME Research, USCD

Predicted Properties

Property	Value	Source
water solubility	4.90e-01 g/l	ALOGPS
logP	0.53	ALOGPS
logP	0.83	ChemAxon
logS	-2.7	ALOGPS
pKa (strongest acidic)	14.03	ChemAxon
pKa (strongest basic)	9.67	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	4	ChemAxon
hydrogen donor count	3	ChemAxon
polar surface area	70.59	ChemAxon
rotatable bond count	7	ChemAxon
refractivity	75.24	ChemAxon
polarizability	30.39	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D05587
KEGG Compound	C11696
ChEBI	258351
ChEMBL	258351
Therapeutic Targets Database	DAP000940
PharmGKB	PA164752820
Wikipedia	http://en.wikipedia.org/wiki/Practolol

ATC Codes

C07AB01

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction
Acetohexamide	The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
Chlorpropamide	The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
Clonidine	Increased hypertension when clonidine stopped
Dihydroergotamine	Ischemia with risk of gangrene
Disopyramide	The beta-blocker, practolol, may increase the toxicity of disopyramide.
Epinephrine	Hypertension, then bradycardia
Ergotamine	Ischemia with risk of gangrene
Fenoterol	Antagonism
Formoterol	Antagonism
Gliclazide	The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
Glyburide	The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
Ibuprofen	Risk of inhibition of renal prostaglandins
Indomethacin	Risk of inhibition of renal prostaglandins
Insulin	The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
Insulin Glargine	The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
Methysergide	Ischemia with risk of gangrene
Orciprenaline	Antagonism
Oxprenolol	Antagonism
Pipobroman	Antagonism
Piroxicam	Risk of inhibition of renal prostaglandins
Prazosin	Risk of hypotension at the beginning of therapy
Repaglinide	The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
Terbutaline	Antagonism

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 Gene: ADRB1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 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 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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:

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
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
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
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 February 08, 2013 16:20