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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H21NO2.ClH
Molecular Weight 295.804
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOPROPRANOLOL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=ZMRUPTIKESYGQW-UQKRIMTDSA-N
InChI=1S/C16H21NO2.ClH/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;1H/t14-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1987
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

1987
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

1987
PubMed

PubMed

TitleDatePubMed
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 Fri Dec 15 15:22:38 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:38 GMT 2023
Record UNII
YP6GDU0L78
Record Status Validated (UNII)
Record Version
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Name Type Language
LEVOPROPRANOLOL HYDROCHLORIDE
Common Name English
PROPRANOLOL HYDROCHLORIDE, (S)-
Common Name English
PROPRANOLOL HYDROCHLORIDE, L-
Common Name English
2-PROPANOL, 1-(ISOPROPYLAMINO)-3-(1-NAPHTHYLOXY)-, HYDROCHLORIDE, (-)-
Systematic Name English
S-(-)-1-ISOPROPYLAMINO-3-(1-NAPHTHOXY)-2-PROPANOL HYDROCHLORIDE
Common Name English
L-(-)-PROPRANOLOL HYDROCHLORIDE
Common Name English
(S)-(-)-PROPRANOLOL HYDROCHLORIDE
Common Name English
PROPRANOLOL HYDROCHLORIDE, (-)-
Common Name English
2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-(1-NAPHTHALENYLOXY)-, HYDROCHLORIDE, (S)-
Systematic Name English
(S)-(-)-1-((1-METHYLETHYL)AMINO)-3-(1-NAPHTHALENYLOXY)-2-PROPANOL HYDROCHLORIDE
Systematic Name English
L-PROPRANOLOL CHLORHYDRATE
Common Name English
L-PROPRANOLOL HYDROCHLORIDE
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
224-096-0
Created by admin on Fri Dec 15 15:22:38 GMT 2023 , Edited by admin on Fri Dec 15 15:22:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID50873367
Created by admin on Fri Dec 15 15:22:38 GMT 2023 , Edited by admin on Fri Dec 15 15:22:38 GMT 2023
PRIMARY
FDA UNII
YP6GDU0L78
Created by admin on Fri Dec 15 15:22:38 GMT 2023 , Edited by admin on Fri Dec 15 15:22:38 GMT 2023
PRIMARY
PUBCHEM
165193
Created by admin on Fri Dec 15 15:22:38 GMT 2023 , Edited by admin on Fri Dec 15 15:22:38 GMT 2023
PRIMARY
CAS
4199-10-4
Created by admin on Fri Dec 15 15:22:38 GMT 2023 , Edited by admin on Fri Dec 15 15:22:38 GMT 2023
PRIMARY
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