Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H19NO.ClH |
Molecular Weight | 265.778 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC(C)NCC(O)C1=CC=C2C=CC=CC2=C1
InChI
InChIKey=QONLGXRPRAIDGI-UHFFFAOYSA-N
InChI=1S/C15H19NO.ClH/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;1H
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 |
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Blockade of epinephrine- and ouabain-induced cardiac arrhythmias in the dog heart-lung preparation. | 1966 May |
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The mechanics of left ventricular contraction in acute experimental cardiac failure. | 1967 Mar |
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The use of metoprolol CR/XL in the treatment of patients with diabetes and chronic heart failure. | 2006 |
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Putting theory into practice: James Black, receptor theory and the development of the beta-blockers at ICI, 1958-1978. | 2006 Jan |
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A case of serendipity*. | 2008 Jun |
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Antagonist affinity measurements at the Gi-coupled human histamine H3 receptor expressed in CHO cells. | 2008 Jun 6 |
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.
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Classification Tree | Code System | Code | ||
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IARC | Pronetalol hydrochloride |
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020IJC48OF
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100000085089
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SUB04074MIG
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758482
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51-02-5
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60975
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m1239
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DTXSID3021194
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ACTIVE MOIETY
SUBSTANCE RECORD