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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
[Betamed in the treatment of psychogenic disorders with a somatic component].	1983 Sep 30	6359726
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
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.	1999 Feb 19	10079020
Partial agonistic properties of (+/-)-pindolol at atypical beta-adrenoceptors in the guinea pig gastric fundus.	2001	11729357
Orthovanadate decreases leptin secretion from isolated mouse fat pads.	2001 Apr	11305589
Nebivolol induces calcium-independent signaling in endothelial cells by a possible beta-adrenergic pathway.	2001 Aug	11483868
Beta(3)-adrenoceptors control Cl(-) conductance in rabbit nasal epithelium.	2001 Jun 22	11430932
Agonistic activity of SR59230A at atypical beta-adrenoceptors in guinea pig gastric fundus and duodenum.	2001 Mar 23	11282126
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
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.	2002 Jan	11815381
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
Atypical cardiostimulant beta-adrenoceptor in the rat heart: stereoselective antagonism by bupranolol but lack of effect by some bupranolol analogues.	2003 Aug	12922943
Comparison between CL-316243- and CGP-12177A-induced relaxations in isolated canine ureter.	2003 Jul	12784085
[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
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].	2003 Oct-Dec	14971294
Atypical beta-adrenoceptors, different from beta 3-adrenoceptors and probably from the low-affinity state of beta 1-adrenoceptors, relax the rat isolated mesenteric artery.	2003 Sep	12967929
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
Effect of cyclodextrins on the complexation and transdermal delivery of bupranolol through rat skin.	2004 Mar 1	15129982
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
[Distribution and property of anti-beta3-adrenoceptor autoantibody in patients with heart failure].	2005 Dec	16563283
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
Potential involvement of a propranolol-insensitive atypical beta-adrenoceptor the vasodilator effect of cyanopindolol in the human pulmonary artery.	2006 Sep	17033087
Is the beta3-adrenoceptor (ADRB3) a potential target for uterorelaxant drugs?	2007 Jun 1	17570158
Pharmacological characterization of the beta-adrenoceptor that mediates the relaxant response to noradrenaline in guinea-pig tracheal smooth muscle.	2007 Mar	17237919
The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder.	2007 Nov 14	17632099
Control of transdermal permeation of hydrocortisone acetate from hydrophilic and lipophilic formulations.	2008	18563577
Role of chemical structure in stereoselective recognition of beta-blockers by cyclodextrins in capillary zone electrophoresis.	2008 Apr 24	18022245
Impairment of NO-dependent relaxation in intralobar pulmonary arteries: comparison of urban particulate matter and manufactured nanoparticles.	2008 Oct	18941568
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
Amphiphilic poly{[alpha-maleic anhydride-omega-methoxy-poly(ethylene glycol)]-co-(ethyl cyanoacrylate)} graft copolymer nanoparticles as carriers for transdermal drug delivery.	2009	19918369
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
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:20:11 UTC 2023` Edited by `admin` on `Fri Dec 15 17:20:11 UTC 2023`
Record UNII	DTC2G3GDPL
Record Status	`Validated (UNII)`
Record Version

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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