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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H21NO2
Molecular Weight 259.3434
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOPROPRANOLOL

SMILES

CC(C)NC[C@H](O)COC1=C2C=CC=CC2=CC=C1

InChI

InChIKey=AQHHHDLHHXJYJD-AWEZNQCLSA-N
InChI=1S/C16H21NO2/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16/h3-9,12,14,17-18H,10-11H2,1-2H3/t14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H21NO2
Molecular Weight 259.3434
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23403082 | https://www.ncbi.nlm.nih.gov/pubmed/19734910

(-)-Propranolol is a small molecule β-adrenergic receptor antagonist and the active isomer of (±)-Propranolol preparations. (-)-Propranolol blocks the binding of epinephrine, norepinephrine, and other endogenous catecholamines to the β-adrenergic receptor, impeding increases in cardiac flow velocity and general stimulation of the sympathetic nervous system signaled by the association of these molecules to the β-adrenergic receptor. In addition to blockade of agonist binding, antagonism of the β-adrenergic receptor by (-)-Propranolol produces negative chronotropic and inotropic action, effectively dampening the force and rate of cardiac contraction. These negative chronotropic and inotropic effects correlate to a demonstrated suppression of adrenaline-induced cardiac arrhythmia by (-)-Propranolol. Suppression of β-adrenergic receptor activation by (-)-Propranolol has been widely exploited in counteracting situations sensitive to heightened cardiac activity including hypertension, angina pectoris, and cardiac ischemia.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
INDERAL LA

Approved Use

Propranolol hydrochloride extended-release capsules are indicated in the management of hypertension. It may be used alone or used in combination with other antihypertensive agents, particularly a thiazide diuretic. Propranolol hydrochloride extended-release capsules is not indicated in the management of hypertensive emergencies. Due to Coronary Atherosclerosis Propranolol hydrochloride extended-release capsules are indicated to decrease angina frequency and increase exercise tolerance in patients with angina pectoris. Propranolol hydrochloride extended-release capsules are indicated for the prophylaxis of common migraine headache. The efficacy of propranolol in the treatment of a migraine attack that has started has not been established, and propranolol is not indicated for such use. Propranolol hydrochloride extended-release capsules improve NYHA functional class in symptomatic patients with hypertrophic subaortic stenosis.

Launch Date

5.42937612E11
Primary
INDERAL LA

Approved Use

Propranolol hydrochloride extended-release capsules are indicated in the management of hypertension. It may be used alone or used in combination with other antihypertensive agents, particularly a thiazide diuretic. Propranolol hydrochloride extended-release capsules is not indicated in the management of hypertensive emergencies. Due to Coronary Atherosclerosis Propranolol hydrochloride extended-release capsules are indicated to decrease angina frequency and increase exercise tolerance in patients with angina pectoris. Propranolol hydrochloride extended-release capsules are indicated for the prophylaxis of common migraine headache. The efficacy of propranolol in the treatment of a migraine attack that has started has not been established, and propranolol is not indicated for such use. Propranolol hydrochloride extended-release capsules improve NYHA functional class in symptomatic patients with hypertrophic subaortic stenosis.

Launch Date

5.42937612E11
Preventing
INDERAL LA

Approved Use

Propranolol hydrochloride extended-release capsules are indicated in the management of hypertension. It may be used alone or used in combination with other antihypertensive agents, particularly a thiazide diuretic. Propranolol hydrochloride extended-release capsules is not indicated in the management of hypertensive emergencies. Due to Coronary Atherosclerosis Propranolol hydrochloride extended-release capsules are indicated to decrease angina frequency and increase exercise tolerance in patients with angina pectoris. Propranolol hydrochloride extended-release capsules are indicated for the prophylaxis of common migraine headache. The efficacy of propranolol in the treatment of a migraine attack that has started has not been established, and propranolol is not indicated for such use. Propranolol hydrochloride extended-release capsules improve NYHA functional class in symptomatic patients with hypertrophic subaortic stenosis.

Launch Date

5.42937612E11
PubMed

PubMed

TitleDatePubMed
Apomorphine hypothermia: interaction with serotonergic agents.
1980 Jan-Feb
The effects of propranolol stereoisomers on nomotopic and ectopic cardiac automaticity in the rat.
1987 Oct
Patents

Patents

Sample Use Guides

80 mg b.i.d.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:49:57 UTC 2023
Edited
by admin
on Wed Jul 05 22:49:57 UTC 2023
Record UNII
74MLR03FLC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOPROPRANOLOL
Common Name English
(2S)-PROPRANOLOL
Common Name English
2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-(1-NAPHTHALENYLOXY)-, (2S)-
Systematic Name English
(-)-PROPRANOLOL
Common Name English
2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-(1-NAPHTHALENYLOXY)-, (S)-
Systematic Name English
S-(-)-PROPRANOLOL
Common Name English
PROPRANOLOL, L-
Common Name English
L-PROPRANOLOL
Common Name English
PROPRANOLOL, (S)-
Common Name English
S-(-)-1-ISOPROPYLAMINO-3-(1-NAPHTHOXY)-2-PROPANOL
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
224-095-5
Created by admin on Wed Jul 05 22:49:57 UTC 2023 , Edited by admin on Wed Jul 05 22:49:57 UTC 2023
PRIMARY
FDA UNII
74MLR03FLC
Created by admin on Wed Jul 05 22:49:57 UTC 2023 , Edited by admin on Wed Jul 05 22:49:57 UTC 2023
PRIMARY
CAS
4199-09-1
Created by admin on Wed Jul 05 22:49:57 UTC 2023 , Edited by admin on Wed Jul 05 22:49:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID90873366
Created by admin on Wed Jul 05 22:49:57 UTC 2023 , Edited by admin on Wed Jul 05 22:49:57 UTC 2023
PRIMARY
PUBCHEM
91536
Created by admin on Wed Jul 05 22:49:57 UTC 2023 , Edited by admin on Wed Jul 05 22:49:57 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER