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
Assessment of beta-blocking activity of low-dose bupranolol.	1989	2565296
Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor.	1993 Dec	7903415
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
(+/-)-Pindolol acts as a partial agonist at atypical beta-adrenoceptors in the guinea pig duodenum.	2001 Jan	11243572
Agonistic activity of SR59230A at atypical beta-adrenoceptors in guinea pig gastric fundus and duodenum.	2001 Mar 23	11282126
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
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.	2002 Jan	11815381
Beta2- and beta3-adrenoreceptor agonists: human myometrial selectivity and effects on umbilical artery tone.	2002 Sep	12237641
Characterization of adrenoceptor involvement in skeletal and cardiac myotoxicity Induced by sympathomimetic agents: toward a new bioassay for beta-blockers.	2003 Apr	12658052
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
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
Aspartate138 is required for the high-affinity ligand binding site but not for the low-affinity binding site of the beta1-adrenoceptor.	2004 Sep	15322738
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
Is the beta3-adrenoceptor (ADRB3) a potential target for uterorelaxant drugs?	2007 Jun 1	17570158
The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder.	2007 Nov 14	17632099
Role of chemical structure in stereoselective recognition of beta-blockers by cyclodextrins in capillary zone electrophoresis.	2008 Apr 24	18022245
Pulsatile changes in free fatty acids augment hepatic glucose production and preserves peripheral glucose homeostasis.	2010 Jul	20424137

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