DEXPROPRANOLOL HYDROCHLORIDE

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 DEXPROPRANOLOL HYDROCHLORIDE

Structure Search

SMILES

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

InChI

InChIKey=ZMRUPTIKESYGQW-PFEQFJNWSA-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-;/m1./s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19108278

(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

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor beta 87 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19108278	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias.	1968 Sep	19108278
Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity.	1999 Dec	10565843
Ectopic and abnormal hormone receptors in adrenal Cushing's syndrome.	2001 Feb	11159817
Potentiation by aminoethylisothiourea of the extra-cellular Ca(2+) component of norepinephrine-induced contraction in rat femoral arteries.	2001 Jan 1	11137715
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	11114249
Enantioselective metabolism of propanolol in isolated hepatocytes prepared from untreated, PB- or 3-MC-pretreated rats.	2001 Mar 1	11279838
KCNQ1 and KCNH2 mutations associated with long QT syndrome in a Chinese population.	2002 Dec	12442276
Solubility, metastable zone width, and racemic characterization of propranolol hydrochloride.	2002 May 5	11968072
The effect of various surfactants on the release rate of propranolol hydrochloride from hydroxypropylmethylcellulose (HPMC)-Eudragit matrices.	2002 Nov	12445567
Renal mechanisms involved in stress-induced antinatriuresis and antidiuresis in rats.	2003 Jul	14972749
Solubilization of cationic drugs in lung surfactant.	2003 Nov	14661933
[Psychosomatic ratios and their correction in the autonomic dysfunction of the sinus node].	2004	15584595
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	16110851
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Activation of BK channels in GH3 cells by a c-PLA2-dependent G-protein signaling pathway.	2005 Jun	15647401
Barakol suppresses norepinephrine-induced inhibition of spontaneous longitudinal smooth muscle contractions in isolated rat small intestine.	2005 Oct 3	16043318
Insights into cyclodextrin interactions during sample stacking using capillary isotachophoresis with on-line microcoil NMR detection.	2005 Sep	16049945

Patents

Sample Use Guides

In Vivo Use Guide

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 HYDROCHLORIDE

Official Name

English

NSC-757295

Code

English

(2R)-1-((1-METHYLETHYL)AMINO)-3-(NAPHTHALEN-1-YLOXY)PROPAN-2-OL HYDROCHLORIDE

Systematic Name

English

DEXPROPRANOLOL HCL

Common Name

English

AY-20694

Code

English

(+)-1-(ISOPROPYLAMINO)-3-(1-NAPHTHYLOXY)-2-PROPANOL HYDROCHLORIDE

Systematic Name

English

PROPRANOLOL HYDROCHLORIDE, (R)-

Common Name

English

DEXPROPRANOLOL HYDROCHLORIDE [USAN]

Common Name

English

I.C.I. 47,319

Code

English

ICI-47319

Code

English

2-PROPANOL, 1-((1-METHYLETHYL)-AMINO)-3-(1-NAPHTHALENYLOXY)-, HYDROCHORIDE, (R)-

Common Name

English

AY-20,694

Code

English

Code System Code Type Description

FDA UNII

AB9DB0NX46