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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

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

(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
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
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:49:58 UTC 2023
Edited
by admin
on Wed Jul 05 22:49:58 UTC 2023
Record UNII
PG6KY07UD7
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
Code System Code Type Description
CHEBI
8736
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
PUBCHEM
21138
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
ChEMBL
CHEMBL275742
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
CAS
5051-22-9
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
DRUG BANK
DB03322
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
SMS_ID
100000083431
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
EVMPD
SUB07044MIG
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
EPA CompTox
DTXSID3045304
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
ECHA (EC/EINECS)
225-749-2
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
INN
2638
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
NCI_THESAURUS
C77944
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
FDA UNII
PG6KY07UD7
Created by admin on Wed Jul 05 22:49:58 UTC 2023 , Edited by admin on Wed Jul 05 22:49:58 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY