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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11466176Curator'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
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23403082 |
1.4 nM [Ki] | ||
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23403082 |
0.54 nM [Ki] | ||
Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9435911 |
4100.0 nM [Ki] | ||
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11466176 |
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Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11466176 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | INDERAL LA Approved UsePropranolol 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 Date1987 |
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Primary | INDERAL LA Approved UsePropranolol 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 Date1987 |
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Preventing | INDERAL LA Approved UsePropranolol 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 Date1987 |
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PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Stereoselective hemodynamic effects of (R)-and (S)-propranolol in man. | 1989 Apr |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11466176
80 mg b.i.d.
Route of Administration:
Intravenous
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224-095-5
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74MLR03FLC
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4199-09-1
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DTXSID90873366
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91536
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SUBSTANCE RECORD