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
SMILES
CC(C)NC[C@H](O)COC1=CC=CC=C1CC=C
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
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/4394971Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1055427
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4394971
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2111395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1055427 |
7.0 nM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hypotensive action of beta-blocking drugs injected into the cerebral ventricle of the rat. | 1978-03 |
|
| Identification of cardiac beta-adrenergic receptors by (minus) [3H]alprenolol binding. | 1975-04 |
|
| Effects of (plus or minus)-propranolol, (plus or minus)-,(plus)-, and (minus)-alprenolol on unanaesthetized dogs with ventricular arrhythmias resulting from coronary artery ligation. | 1970-08 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4394971
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4398743
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
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3J532ZIY9K
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RACEMATE -> ENANTIOMER |