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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 DEXPROPRANOLOL

SMILES

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

InChI

InChIKey=AQHHHDLHHXJYJD-CQSZACIVSA-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-/m1/s1

HIDE SMILES / InChI
(R)-(+)-Propranolol (also known as DEXPROPRANOLOL) is the less active enantiomer of propranolol and is an antagonist of the beta-adrenergic receptor. It is known, that propranolol had been used for myocardial infarction; arrhythmia, anxiety and some other disease, but adverse effects instigated the replacement by newer drugs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias.
1968 Sep
Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity.
1999 Dec
Ectopic and abnormal hormone receptors in adrenal Cushing's syndrome.
2001 Feb
Potentiation by aminoethylisothiourea of the extra-cellular Ca(2+) component of norepinephrine-induced contraction in rat femoral arteries.
2001 Jan 1
Structural basis for enantiomer binding and separation of a common beta-blocker: crystal structure of cellobiohydrolase Cel7A with bound (S)-propranolol at 1.9 A resolution.
2001 Jan 5
Enantioselective metabolism of propanolol in isolated hepatocytes prepared from untreated, PB- or 3-MC-pretreated rats.
2001 Mar 1
KCNQ1 and KCNH2 mutations associated with long QT syndrome in a Chinese population.
2002 Dec
Solubility, metastable zone width, and racemic characterization of propranolol hydrochloride.
2002 May 5
The effect of various surfactants on the release rate of propranolol hydrochloride from hydroxypropylmethylcellulose (HPMC)-Eudragit matrices.
2002 Nov
Renal mechanisms involved in stress-induced antinatriuresis and antidiuresis in rats.
2003 Jul
Solubilization of cationic drugs in lung surfactant.
2003 Nov
[Psychosomatic ratios and their correction in the autonomic dysfunction of the sinus node].
2004
Catecholaminergic consolidation of motor cortical neuroplasticity in humans.
2004 Nov
Evaluation of endoscopic variceal ligation (EVL) versus propanolol plus isosorbide mononitrate/nadolol (ISMN) in the prevention of variceal rebleeding: comparison of cirrhotic and noncirrhotic patients.
2005 Aug
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Activation of BK channels in GH3 cells by a c-PLA2-dependent G-protein signaling pathway.
2005 Jun
Barakol suppresses norepinephrine-induced inhibition of spontaneous longitudinal smooth muscle contractions in isolated rat small intestine.
2005 Oct 3
Insights into cyclodextrin interactions during sample stacking using capillary isotachophoresis with on-line microcoil NMR detection.
2005 Sep
Patents

Patents

Sample Use Guides

in cats: received an intravenous infusion of (+)-propranolol at 0.5 mg/min exhibited a prompt return to sinus rhythm after a mean total dose of 6.5 + 0.9 mg/kg. The final heart rate was an average of 48 beats/min below the initial rate. The difference between the antiarrhythmic doses of (+)- and (- )-propranolol was statistically significant (P<0.01).
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Name Type Language
DEXPROPRANOLOL
INN  
INN  
Official Name English
dexpropranolol [INN]
Common Name English
PROPRANOLOL, (R)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
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Code System Code Type Description
CHEBI
8736
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PUBCHEM
21138
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ChEMBL
CHEMBL275742
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CAS
5051-22-9
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DRUG BANK
DB03322
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SMS_ID
100000083431
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EVMPD
SUB07044MIG
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EPA CompTox
DTXSID3045304
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ECHA (EC/EINECS)
225-749-2
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INN
2638
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NCI_THESAURUS
C77944
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FDA UNII
PG6KY07UD7
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