Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H19NO |
Molecular Weight | 229.3175 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NCC(O)C1=CC=C2C=CC=CC2=C1
InChI
InChIKey=HRSANNODOVBCST-UHFFFAOYSA-N
InChI=1S/C15H19NO/c1-11(2)16-10-15(17)14-8-7-12-5-3-4-6-13(12)9-14/h3-9,11,15-17H,10H2,1-2H3
Molecular Formula | C15H19NO |
Molecular Weight | 229.3175 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Pronetalol (Pronethalol) is a nonselective beta-adrenoceptor antagonist that is structurally related to propranolol. Pronethalol displays a ∼125–150-fold lower affinity (140–830 nM) for beta-adrenoceptors than propranolol (1.1–5.7 nM). Pronethalol was the first beta-adrenoceptor antagonist used for the treatment of coronary heart disease and cardiac arrhythmias. Pronethalol is a cationic-amphiphilic agent that exhibits membrane-stabilizing effects that are unrelated to beta-adrenoceptor blockade. Pronetalol itself never came into widespread
clinical use; it was found to produce thymic tumors in mice, and was discarded in favor of a similar, safer compound, ICI 45,520.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Blockade of epinephrine- and ouabain-induced cardiac arrhythmias in the dog heart-lung preparation. | 1966 May |
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Tremorine-oxotremorine-induced tremor, hypothermia and analgesia, and physostigmine toxicity, in mice after pretreatment with beta-adrenoceptor antagonists. | 1976 Apr |
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Determination of propranolol concentration in small volume of rat plasma by HPLC with fluorometric detection. | 2001 Dec |
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Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells. | 2008 Jun 6 |
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Comparison of some properties of pronethalol and propranolol. 1965. | 2010 Jul |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14110746
Guinea-pigs: In one series of experiments, 5 mg/kg of pronethalol was injected, and in another 15 mg/kg. Pronethalol (5 mg/kg), increased the dose of ouabain required to produce extrasystoles, completely prevented fibrillation, and significantly raised the lethal dose of ouabain. When fibrillation had already been produced by ouabain, pronethalol (3 to 4 mg) administered slowly restored a regular rhythm, but rapid injection sometimes produced cardiac arrest. As much as 20 to 25 mg/kg of pronethalol could be given to animals deeply anaesthetized with urethane or pentobarbitone, but with light chloroform or ether anaesthesia, 5 mg/kg of pronethalol caused a large fall in blood pressure and complete heart-block.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4389284
Pronethalol (6.8 x 10(-5)M) reversed the alpha-receptor blockade by dibenamine, ergotamine and phentolamine of responses to adrenaline, noradrenaline and phenylephrine in guinea-pig seminal vesicle.
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 17:50:09 GMT 2023
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on
Sat Dec 16 17:50:09 GMT 2023
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Record UNII |
XBP4RT1IMQ
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Validated (UNII)
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NCI_THESAURUS |
C29576
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C82257
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SUPERSEDED |
Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |