BUPRANOLOL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H22ClNO2.ClH
Molecular Weight	308.244
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC1=CC(OCC(O)CNC(C)(C)C)=C(Cl)C=C1

InChI

InChIKey=WJUUZHQWGKSLIJ-UHFFFAOYSA-N

InChI=1S/C14H22ClNO2.ClH/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4;/h5-7,11,16-17H,8-9H2,1-4H3;1H

HIDE SMILES / InChI

Description
Sources: http://cursoenarm.net/UPTODATE/contents/mobipreview.htm?19/1/19484 | https://www.drugbank.ca/drugs/DB08808 | https://www.drugs.com/international/bupranolol.html | https://www.ncbi.nlm.nih.gov/pubmed/26456674

Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Bupranolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension. Ophthalmic Bupranolol is used for the management of glaucoma and oral Bupranolol is used for the management of cardiovascular disorders. S-Bupranolol has also being shown to have superior preclinical safety profile and great antinociceptive efficacy and should be considered as a unique b-AR compound to advance future clinical pain studies.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.drugbank.ca/drugs/DB08808 \| https://www.ncbi.nlm.nih.gov/pubmed/10079020 \| https://www.ncbi.nlm.nih.gov/pubmed/10411574	Antagonist 2778	5.2 nM [Ki]
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://www.drugbank.ca/drugs/DB08808 \| https://www.ncbi.nlm.nih.gov/pubmed/10079020 \| https://www.ncbi.nlm.nih.gov/pubmed/10411574	Antagonist 2778	50.0 nM [Ki]
Beta-3 adrenergic receptor 49 Target ID: CHEMBL246 Sources: https://www.drugbank.ca/drugs/DB08808 \| https://www.ncbi.nlm.nih.gov/pubmed/10411574 \| https://www.ncbi.nlm.nih.gov/pubmed/7903415	Antagonist 2778	170.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/381835 https://www.ncbi.nlm.nih.gov/pubmed/106216 https://www.ncbi.nlm.nih.gov/pubmed/2565296	Primary		Approved 8429	Betadrenol Approved Use Hypertension Launch Date 1968
Glaucoma 57 Sources: http://cursoenarm.net/UPTODATE/contents/mobipreview.htm?19/1/19484 https://www.ncbi.nlm.nih.gov/pubmed/439706	Primary		Approved 8429	Ophtorenin Approved Use Glaucoma treatment

PubMed

Title	Date	PubMed
Carazolol: a potent, selective beta 3-adrenoceptor agonist.	1995 Nov 30	8719421
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.	1999 Feb 19	10079020
Structure-activity relationship studies of (+/-)-terbutaline and (+/-)-fenoterol on beta3-adrenoceptors in the guinea pig gastric fundus.	2001 Aug	11885748
beta3-Adrenergic regulation of an ion channel in the heart-inhibition of the slow delayed rectifier potassium current I(Ks) in guinea pig ventricular myocytes.	2002 Dec	12445880
Orthovanadate decreases the leptin content in isolated mouse fat pads via proteasome activation.	2002 Oct 15	12361713
Characterization of adrenoceptor involvement in skeletal and cardiac myotoxicity Induced by sympathomimetic agents: toward a new bioassay for beta-blockers.	2003 Apr	12658052
beta3-Adrenergic stimulation produces a decrease of cardiac contractility ex vivo in mice overexpressing the human beta3-adrenergic receptor.	2003 Aug 1	12909312
Pharmacological evidence for beta3 adrenoceptors in the control of rat gastric acid secretion.	2003 Feb	12643612
Comparison between CL-316243- and CGP-12177A-induced relaxations in isolated canine ureter.	2003 Jul	12784085
Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor.	2003 Jun	12761341
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].	2003 Oct-Dec	14971294
Endothelial beta3-adrenoceptors mediate vasorelaxation of human coronary microarteries through nitric oxide and endothelium-dependent hyperpolarization.	2004 Aug 24	15302798
Potential involvement of a propranolol-insensitive atypical beta-adrenoceptor the vasodilator effect of cyanopindolol in the human pulmonary artery.	2006 Sep	17033087
Nebivolol in the treatment of chronic heart failure.	2007	18078016
Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors.	2009 Mar	19439807

Patents

Sample Use Guides

In Vivo Use Guide

Bupranolol is usually given in doses of 100 mg twice daily in the treatment of hypertension

Route of Administration: Oral

In Vitro Use Guide

In the human detrusor bupranolol (a nonselective β-AR antagonist) at a low concentration (10(-8) M) did not inhibit isoproterenol-induced relaxation, but at higher concentrations (10(-7)-10(-5) M), the drug caused a rightward shift of the concentration-relaxation curve for isoproterenol in a dose-dependent manner

Name

Type

Language

BUPRANOLOL HYDROCHLORIDE

Common Name

English

Bupranolol hydrochloride [WHO-DD]

Common Name

English

1-(TERT-BUTYLAMINO)-3-((6-CHLORO-M-TOLYL)-OXY)-2-PROPANOL HYDROCHLORIDE

Systematic Name

English

LOOSER

Brand Name

English

PANIMIT

Brand Name

English

B 1312

Code

English

BETADRENOL

Brand Name

English

BUPRANOLOL HYDROCHLORIDE [MART.]

Common Name

English

KL-255

Code

English

BETADRAN

Brand Name

English

KL-255 (AS HYDROCHLORIDE)

Code

English

BUPRANOLOL HYDROCHLORIDE [JAN]

Common Name

English

BUPRANOLOL HYDROCHLORIDE [MI]

Common Name

English

B-1312

Code

English

BUPRANOLOL HCL

Common Name

English

Code System Code Type Description

FDA UNII

DTC2G3GDPL