NAV

Practolol

Identification

Generic Name
Practolol
DrugBank Accession Number
DB01297
Background

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

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 266.3361
Monoisotopic: 266.16304258
Chemical Formula
C14H22N2O3
Synonyms
  • (±)-practolol
  • 1-(4-acetamidophenoxy)-3-isopropylamino-2-propanol
  • 4'-(2-hydroxy-3-(isopropylamino)propoxy)acetanilide
  • N-(4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)phenyl)acetamide
  • Practolol
  • Practololo
  • Practololum
  • Praktololu
External IDs
  • AY-21,011
  • AY-21011
  • I.C.I. 50,172
  • I.C.I.-50,172
  • ICI-50172
  • Tocris-0831

Pharmacology

Indication

Used in the emergency treatment of cardiac arrhythmias.

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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Humans
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

Adverse Effects
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Toxicity

Symptoms of overdose include abdominal irritation, central nervous system depression, coma, extremely slow heartbeat, heart failure, lethargy, low blood pressure, and wheezing.

Pathways
PathwayCategory
Practolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbaloparatideAbaloparatide may increase the hypotensive activities of Practolol.
AbataceptThe metabolism of Practolol can be increased when combined with Abatacept.
AbirateroneThe metabolism of Practolol can be decreased when combined with Abiraterone.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Practolol.
AcebutololAcebutolol may increase the arrhythmogenic activities of Practolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Practolol.
AcemetacinAcemetacin may decrease the antihypertensive activities of Practolol.
AcetaminophenThe metabolism of Practolol can be decreased when combined with Acetaminophen.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Practolol.
AcetophenazineThe serum concentration of Practolol can be increased when it is combined with Acetophenazine.
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Food Interactions
  • Avoid alcohol.
  • Avoid natural licorice.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Practolol hydrochlorideAT88RXS5AE6996-43-6UEWORNJBQXFYSM-UHFFFAOYSA-N

Categories

ATC Codes
C07AB01 — Practolol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Acetanilides
Alternative Parents
N-acetylarylamines / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Acetamides / Secondary carboxylic acid amides / Secondary alcohols / Amino acids and derivatives / 1,2-aminoalcohols / Dialkylamines
show 4 more
Substituents
1,2-aminoalcohol / Acetamide / Acetanilide / Alcohol / Alkyl aryl ether / Amine / Amino acid or derivatives / Aromatic homomonocyclic compound / Carbonyl group / Carboxamide group
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary alcohol, secondary amino compound, acetamides, ethanolamines, propanolamine (CHEBI:258351)
Affected organisms
Not Available

Chemical Identifiers

UNII
SUG9176GRW
CAS number
6673-35-4
InChI Key
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)
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

References

General References
Not Available
Human Metabolome Database
HMDB0015411
KEGG Drug
D05587
KEGG Compound
C11696
PubChem Compound
4883
PubChem Substance
46507496
ChemSpider
4715
BindingDB
25749
RxNav
8620
ChEBI
258351
ChEMBL
CHEMBL6995
Therapeutic Targets Database
DAP000940
PharmGKB
PA164752820
Wikipedia
Practolol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)134-136 °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 RuleNoChemaxon
MDDR-like RuleNoChemaxon
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 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.6103
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dm-3900000000-6e93acc67e2905952d4e

Targets

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Details1. Beta-1 adrenergic receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor signaling protein activity
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 e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
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. [Article]
  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. [Article]
  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. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  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. [Article]

Enzymes

Details1. Cytochrome P450 2D6
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Sternieri E, Coccia CP, Pinetti D, Guerzoni S, Ferrari A: Pharmacokinetics and interactions of headache medications, part II: prophylactic treatments. Expert Opin Drug Metab Toxicol. 2006 Dec;2(6):981-1007. doi: 10.1517/17425255.2.6.981 . [Article]
  2. Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
  3. Iwaki M, Niwa T, Bandoh S, Itoh M, Hirose H, Kawase A, Komura H: Application of substrate depletion assay to evaluation of CYP isoforms responsible for stereoselective metabolism of carvedilol. Drug Metab Pharmacokinet. 2016 Dec;31(6):425-432. doi: 10.1016/j.dmpk.2016.08.007. Epub 2016 Sep 2. [Article]

Drug created at June 30, 2007 14:19 / Updated at February 21, 2021 18:51