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

Molecular Formula	C14H22ClNO2
Molecular Weight	271.783
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 -3.1536001E10
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
Partial agonistic properties of (+/-)-pindolol at atypical beta-adrenoceptors in the guinea pig gastric fundus.	2001	11729357
Nebivolol induces calcium-independent signaling in endothelial cells by a possible beta-adrenergic pathway.	2001 Aug	11483868
Cardiovascular effects of beta 3-adrenoceptor stimulation in perinephritic hypertension.	2001 Aug	11473569
(+/-)-Pindolol acts as a partial agonist at atypical beta-adrenoceptors in the guinea pig duodenum.	2001 Jan	11243572
Functional properties of atypical beta-adrenoceptors on the guinea pig duodenum.	2001 Mar 23	11282125
Upregulation of functional beta(3)-adrenergic receptor in the failing canine myocardium.	2001 Sep 28	11577025
Synthesis and evaluation of radiolabeled antagonists for imaging of beta-adrenoceptors in the brain with PET.	2002 Feb	11738481
Orthovanadate decreases the leptin content in isolated mouse fat pads via proteasome activation.	2002 Oct 15	12361713
Evidence against beta 3-adrenoceptors or low affinity state of beta 1-adrenoceptors mediating relaxation in rat isolated aorta.	2003 Jan	12522078
[Impairment of atypical beta-adrenergic-mediated relaxation in spontaneously hypertensive rats before and during the development of arterial hypertension].	2003 Jul-Aug	12945229
The beta3-adrenoceptor-mediated relaxation induced by dopamine in guinea pig taenia caecum.	2003 Jun	14572171
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
Endothelial beta3-adrenoceptors mediate vasorelaxation of human coronary microarteries through nitric oxide and endothelium-dependent hyperpolarization.	2004 Aug 24	15302798
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.	2004 May	15060759
Effect of penetration enhancers on the release and skin permeation of bupranolol from reservoir-type transdermal delivery systems.	2005 Jan 20	15620873
Comparison of the alpha-adrenoceptor-mediated effects of beta3-adrenoceptor ligands in rat pulmonary artery.	2005 Jun	16012871
Adrenoceptor heterogeneity in the ruminal epithelium of sheep.	2005 May	15900505
Positive inotropic and lusitropic effects mediated via the low-affinity state of beta1-adrenoceptors in pithed rats.	2005 Nov	16151438
Nebivolol in the treatment of chronic heart failure.	2007	18078016
Effect of DL-nebivolol, its enantiomers and metabolites on the intracellular production of superoxide and nitric oxide in human endothelial cells.	2007 Apr	17280840
The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder.	2007 Nov 14	17632099
Influence of potent and selective beta-adrenoceptor agonist, CL 316243, on the contractile response of non-pregnant human myometrium.	2008 Dec	19261970
Skin permeation mechanism and bioavailability enhancement of celecoxib from transdermally applied nanoemulsion.	2008 Jul 9	18613981
CGP12177-induced haemodynamic and vascular effects in normotensive and hypertensive rats.	2008 Sep 4	18601917
Comparison of the analysis of beta-blockers by different techniques.	2009 Dec 1	19879818
Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors.	2009 Mar	19439807
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:47:17 UTC 2023` Edited by `admin` on `Fri Dec 15 16:47:17 UTC 2023`
Record UNII	858YGI5PIT
Record Status	`Validated (UNII)`
Record Version

Download

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