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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

(-)-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 TargetPharmacologyConditionPotency
1.4 nM [Ki]
0.54 nM [Ki]
4100.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
INDERAL LA
Primary
INDERAL LA
Preventing
INDERAL LA

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
80 mg b.i.d.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
74MLR03FLC
Record Status Validated (UNII)
Record Version