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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H23NO2
Molecular Weight 249.3486
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALPRENOLOL, (S)-

SMILES

CC(C)NC[C@H](O)COC1=C(CC=C)C=CC=C1

InChI

InChIKey=PAZJSJFMUHDSTF-AWEZNQCLSA-N
InChI=1S/C15H23NO2/c1-4-7-13-8-5-6-9-15(13)18-11-14(17)10-16-12(2)3/h4-6,8-9,12,14,16-17H,1,7,10-11H2,2-3H3/t14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H23NO2
Molecular Weight 249.3486
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1055427

(S)-Alprenolol is a more active stereoisomer of antihypertensive beta-blocker alprenolol. Its activity against beta-adrenoreceptor is 100 times greater than the activity of (R)-alprenolol. In a model of ventricular arrhythmias produced by ligation of the left coronary artery, (S)-alprenolol was effective at 7.5 mg/kg, whereas (R)-alprenolol abolished the ventricular arrhythmia by cumulative dose of 15.5 mg/kg. As a most active enantiomer of alprenolol, the compound was used as a tool to study beta-adrenergic receptors.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of (plus or minus)-propranolol, (plus or minus)-,(plus)-, and (minus)-alprenolol on unanaesthetized dogs with ventricular arrhythmias resulting from coronary artery ligation.
1970 Aug
Identification of cardiac beta-adrenergic receptors by (minus) [3H]alprenolol binding.
1975 Apr
Hypotensive action of beta-blocking drugs injected into the cerebral ventricle of the rat.
1978 Mar
Patents

Patents

Sample Use Guides

In a mode of ventricular arrhythmia (S)-Alprenolol was administered to dogs intravenously at 0.5 - 8.0 mg/kg.
Route of Administration: Intravenous
In Vitro Use Guide
Guinea-pig spontaneously beating right atria and tracheal strips were suspended in water-jacketed 10ml tissue baths containing a physiological salt solution. Atria were allowed to equilibrate for 1 hr before any drugs were added. Responses from both tissues were recorded on a Grass polygraph and atrial rates were monitored via 7P4A tachographs. Carbachol (3 × 10 -7 M) was used to induce tone in tracheal strips and added to the bath 15 min prior to determining the relaxing effects of the drug. Selected concentrations of the antagonists were allowed to interact with each tissue for 3, 10, 25, 45, 65, or 120 min before addition of the agonist. All concentrations of antagonists were added in a volume of 0.1 ml.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:52:01 GMT 2023
Edited
by admin
on Sat Dec 16 10:52:01 GMT 2023
Record UNII
3J532ZIY9K
Record Status Validated (UNII)
Record Version
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Name Type Language
ALPRENOLOL, (S)-
Common Name English
(S)-ALPRENOLOL
Common Name English
2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-(2-(2-PROPENYL)PHENOXY)-, (S)-
Systematic Name English
2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-(2-(2-PROPEN-1-YL)PHENOXY)-, (2S)-
Systematic Name English
(-)-ALPRENOLOL
Common Name English
2-PROPANOL, 1-(O-ALLYLPHENOXY)-3-(ISOPROPYLAMINO)-, (-)-
Systematic Name English
Code System Code Type Description
FDA UNII
3J532ZIY9K
Created by admin on Sat Dec 16 10:52:01 GMT 2023 , Edited by admin on Sat Dec 16 10:52:01 GMT 2023
PRIMARY
CAS
23846-71-1
Created by admin on Sat Dec 16 10:52:01 GMT 2023 , Edited by admin on Sat Dec 16 10:52:01 GMT 2023
PRIMARY
PUBCHEM
204665
Created by admin on Sat Dec 16 10:52:01 GMT 2023 , Edited by admin on Sat Dec 16 10:52:01 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER