U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C19H24N2O4.ClH
Molecular Weight 380.866
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOLAMOLOL HYDROCHLORIDE

SMILES

Cl.CC1=C(OCC(O)CNCCOC2=CC=C(C=C2)C(N)=O)C=CC=C1

InChI

InChIKey=ZATQSCRQPQXBEG-UHFFFAOYSA-N
InChI=1S/C19H24N2O4.ClH/c1-14-4-2-3-5-18(14)25-13-16(22)12-21-10-11-24-17-8-6-15(7-9-17)19(20)23;/h2-9,16,21-22H,10-13H2,1H3,(H2,20,23);1H

HIDE SMILES / InChI
Tolamolol is a phenoxypropranolamine derivative that preferentially inhibits myocardial beta adrenoreceptors, possesses beta blocking potency equivalent to propranolol, has little or no direct cell membrane effect and lacks beta adrenergic stimulating action. Cardioselective beta adrenergic blockade with tolamolol was highly effective in controlling ventricular rate in supraventricular arrhythmias and reduced the frequency of ventricular ectopic beats in half of the small group of patients with this arrhythmia. It is particularly applicable in patients with obstructive pulmonary disease in whom cardiac beta adrenergic blockade is indicated. Hypotension is an important potential side effect. Tolamolol and propranolol are equal in anti-anginal efficacy but tolamolol has the advantage of being cardioselective. It is superior to practolol. Tolamolol had no effect on sperm motility.

Approval Year

PubMed

PubMed

TitleDatePubMed
Effect of beta-adrenoceptor blocking drugs, physostigmine, and atropine on the toxicity of doxepin in mice.
1975 Aug
Double-blind comparison of tolamolol, propranolol, practolol, and placebo in the treatment of angina pectoris.
1975 Mar 29
Efficacy of cardioselective beta adrenergic blockade with intravenously administered tolamolol in the treatment of cardiac arrhythmias.
1976 Aug
Antihypertensive action of drug combination: polythiazide, prazosin and tolamolol.
1977 Feb
Beta-adrenergic blockade of the lung. Dose-dependent cardioselectivity of tolamolol in asthma.
1978 Jun
Tolamolol, a beta adrenergic blocking agent: study of its efficacy in angina pectoris.
1978 Sep
Beta-adrenoceptor antagonists and human sperm motility.
1990 Mar

Sample Use Guides

In Vivo Use Guide
200 mg thrice daily for a month
Route of Administration: Oral
Name Type Language
TOLAMOLOL HYDROCHLORIDE
WHO-DD  
Common Name English
Benzamide, 4-[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]ethoxy]-, hydrochloride (1:1)
Systematic Name English
4-(2-(2-HYDROXY-3-O-TOLYLOXYPROPYLAMINO)ETHOXY)BENZAMIDE HYDROCHLORIDE
Common Name English
Tolamolol hydrochloride [WHO-DD]
Common Name English
DL-TOLAMOLOL HYDROCHLORIDE
Common Name English
(±)-TOLAMOLOL HYDROCHLORIDE
Common Name English
BENZAMIDE, 4-(2-((2-HYDROXY-3-(2-METHYLPHENOXY)PROPYL)AMINO)ETHOXY)-, MONOHYDROCHLORIDE, (±)-
Common Name English
Code System Code Type Description
PUBCHEM
170731
Created by admin on Sat Dec 16 10:44:09 GMT 2023 , Edited by admin on Sat Dec 16 10:44:09 GMT 2023
PRIMARY
CAS
43064-17-1
Created by admin on Sat Dec 16 10:44:09 GMT 2023 , Edited by admin on Sat Dec 16 10:44:09 GMT 2023
SUPERSEDED
CAS
51599-37-2
Created by admin on Sat Dec 16 10:44:09 GMT 2023 , Edited by admin on Sat Dec 16 10:44:09 GMT 2023
PRIMARY
SMS_ID
100000084653
Created by admin on Sat Dec 16 10:44:09 GMT 2023 , Edited by admin on Sat Dec 16 10:44:09 GMT 2023
PRIMARY
EVMPD
SUB04905MIG
Created by admin on Sat Dec 16 10:44:09 GMT 2023 , Edited by admin on Sat Dec 16 10:44:09 GMT 2023
PRIMARY
FDA UNII
25619NA95Y
Created by admin on Sat Dec 16 10:44:09 GMT 2023 , Edited by admin on Sat Dec 16 10:44:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID00962876
Created by admin on Sat Dec 16 10:44:09 GMT 2023 , Edited by admin on Sat Dec 16 10:44:09 GMT 2023
PRIMARY