LEVOPROPRANOLOL HYDROCHLORIDE

Possibly Marketed Outside US

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

Structure Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11466176
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta-1 adrenergic receptor 163 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23403082	Antagonist 2849	1.4 nM [Ki]
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23403082	Antagonist 2849	0.54 nM [Ki]
Serotonin 1b (5-HT1b) receptor 45 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9435911	Antagonist 2849	4100.0 nM [Ki]
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11466176	Antagonist 2849
Beta-1 adrenergic receptor 163 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11466176	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Hypertension 575 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Approved 8583	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
Hypertrophic subaortic stenosis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Approved 8583	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
Migraine 107 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Preventing	Approved 8583	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
Unknown 2596

C_max

Value	Dose	Analyte	Population
74.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2642031/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
134 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7696378/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
25 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7696378/	20 mg 3 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
273.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2642031/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
66 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7696378/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
98 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7696378/	20 mg 3 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
4.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2642031/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7696378/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7696378/	20 mg 3 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LEVOPROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2400 mg 1 times / day multiple, oral Highest studied dose Dose: 2400 mg, 1 times / day Route: oral Route: multiple Dose: 2400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/476356/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/476356/	Other AEs: drowsiness, ataxia... Other AEs: drowsiness (3 patients) ataxia (3 patients) hypotension (3 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/476356/
30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	Other AEs: Chills, Fatigue... Other AEs: Chills (1 pt) Fatigue (1 pt) Nausea (1 pt) Autoimmune thyroiditis (1 pt) Pruritus (1 pt) Rash (1 pt) Vitiligo (1 pt) Hypotension (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7356190/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7356190/	Disc. AE: lightheadedness, generalized seizures... AEs leading to discontinuation/dose reduction: lightheadedness (1 pt) generalized seizures (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/7356190/
260 mg single, oral Overdose Dose: 260 mg Route: oral Route: single Dose: 260 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3799650/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3799650/	Disc. AE: ischemic bowel necrosis... AEs leading to discontinuation/dose reduction: ischemic bowel necrosis (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/3799650/

AEs

AE	Significance	Dose	Population
ataxia	3 patients	2400 mg 1 times / day multiple, oral Highest studied dose Dose: 2400 mg, 1 times / day Route: oral Route: multiple Dose: 2400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/476356/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/476356/
drowsiness	3 patients	2400 mg 1 times / day multiple, oral Highest studied dose Dose: 2400 mg, 1 times / day Route: oral Route: multiple Dose: 2400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/476356/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/476356/
hypotension	3 patients	2400 mg 1 times / day multiple, oral Highest studied dose Dose: 2400 mg, 1 times / day Route: oral Route: multiple Dose: 2400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/476356/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/476356/
Autoimmune thyroiditis	1 pt	30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
Chills	1 pt	30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
Fatigue	1 pt	30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
Hypotension	1 pt	30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
Nausea	1 pt	30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
Pruritus	1 pt	30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
Rash	1 pt	30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
Vitiligo	1 pt	30 mg 2 times / day steady-state, oral Highest studied dose\|RP2D Dose: 30 mg, 2 times / day Route: oral Route: steady-state Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/33127652/
generalized seizures	1 pt Disc. AE	2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7356190/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7356190/
lightheadedness	1 pt Disc. AE	2000 mg single, oral Overdose Dose: 2000 mg Route: oral Route: single Dose: 2000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7356190/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7356190/
ischemic bowel necrosis	1 pt Disc. AE	260 mg single, oral Overdose Dose: 260 mg Route: oral Route: single Dose: 260 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3799650/	unknown, ADULT Health Status: unknown Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3799650/

PubMed

Title	Date	PubMed
Stereoselective hemodynamic effects of (R)-and (S)-propranolol in man.	1989-04	2739756
The effects of propranolol stereoisomers on nomotopic and ectopic cardiac automaticity in the rat.	1987-10	3432731
Apomorphine hypothermia: interaction with serotonergic agents.	1980-01-01	7192860

Patents

Sample Use Guides

In Vivo Use Guide

80 mg b.i.d.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Name

Type

Language

(S)-(-)-PROPRANOLOL HYDROCHLORIDE

Preferred Name

English

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

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