BUPRANOLOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H22ClNO2
Molecular Weight	271.783
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=HQIRNZOQPUAHHV-UHFFFAOYSA-N

InChI=1S/C14H22ClNO2/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

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
Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor.	1993 Dec	7903415
Functional properties of atypical beta-adrenoceptors on the guinea pig duodenum.	2001 Mar 23	11282125
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.	2002 Jan	11815381
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
Role of alpha-adrenergic receptors in the effect of the beta-adrenergic receptor ligands, CGP 12177, bupranolol, and SR 59230A, on the contraction of rat intrapulmonary artery.	2004 Apr	14718590
ALpha1-adrenoceptor antagonist properties of CGP 12177A and other beta-adrenoceptor ligands: evidence against beta(3)- or atypical beta-adrenoceptors in rat aorta.	2004 Jun	15205310
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.	2004 May	15060759
Comparison of the alpha-adrenoceptor-mediated effects of beta3-adrenoceptor ligands in rat pulmonary artery.	2005 Jun	16012871
Effect of penetration enhancers on the transdermal delivery of bupranolol through rat skin.	2005 May-Jun	16025846
Transdermal delivery of beta-blockers.	2006 May	16640500
Control of transdermal permeation of hydrocortisone acetate from hydrophilic and lipophilic formulations.	2008	18563577
Skin permeation mechanism and bioavailability enhancement of celecoxib from transdermally applied nanoemulsion.	2008 Jul 9	18613981
beta3-adrenergic receptor activation increases human atrial tissue contractility and stimulates the L-type Ca2+ current.	2008 Sep	18704193
CGP12177-induced haemodynamic and vascular effects in normotensive and hypertensive rats.	2008 Sep 4	18601917
Beta3-adrenoceptor agonists: possible role in the treatment of overactive bladder.	2010 Dec	21221199

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

Official Name

English

B-1312 FREE BASE

Code

English

KL-255 FREE BASE

Code

English

Bupranolol [WHO-DD]

Common Name

English

B 1312 FREE BASE

Code

English

OPHTORENIN

Brand Name

English

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

Systematic Name

English

BUPRANOLOL [MI]

Common Name

English

bupranolol [INN]

Common Name

English

BUPRANOL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29576