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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 of BUPRANOLOL

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 ( + / - )

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.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.4 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPRANOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BUPRANOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [Km 0.27 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
[Betamed in the treatment of psychogenic disorders with a somatic component].
1983 Sep 30
Assessment of beta-blocking activity of low-dose bupranolol.
1989
Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor.
1993 Dec
Carazolol: a potent, selective beta 3-adrenoceptor agonist.
1995 Nov 30
Characterization of adrenoceptor involvement in skeletal and cardiac myotoxicity Induced by sympathomimetic agents: toward a new bioassay for beta-blockers.
2003 Apr
Atypical cardiostimulant beta-adrenoceptor in the rat heart: stereoselective antagonism by bupranolol but lack of effect by some bupranolol analogues.
2003 Aug
beta3-Adrenergic stimulation produces a decrease of cardiac contractility ex vivo in mice overexpressing the human beta3-adrenergic receptor.
2003 Aug 1
Pharmacological evidence for beta3 adrenoceptors in the control of rat gastric acid secretion.
2003 Feb
Comparison between CL-316243- and CGP-12177A-induced relaxations in isolated canine ureter.
2003 Jul
[Impairment of atypical beta-adrenergic-mediated relaxation in spontaneously hypertensive rats before and during the development of arterial hypertension].
2003 Jul-Aug
The beta3-adrenoceptor-mediated relaxation induced by dopamine in guinea pig taenia caecum.
2003 Jun
Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor.
2003 Jun
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].
2003 Oct-Dec
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
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
Endothelial beta3-adrenoceptors mediate vasorelaxation of human coronary microarteries through nitric oxide and endothelium-dependent hyperpolarization.
2004 Aug 24
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
Overexpression of beta 1-adrenoceptors in adult rat ventricular myocytes enhances CGP 12177A cardiostimulation: implications for 'putative' beta 4-adrenoceptor pharmacology.
2004 Mar
Effect of cyclodextrins on the complexation and transdermal delivery of bupranolol through rat skin.
2004 Mar 1
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.
2004 May
Screening for library-assisted identification and fully validated quantification of 22 beta-blockers in blood plasma by liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization.
2004 Nov 26
Aspartate138 is required for the high-affinity ligand binding site but not for the low-affinity binding site of the beta1-adrenoceptor.
2004 Sep
Inconsistent role of nitric oxide on lipolysis in isolated rat adipocytes.
2005
[Distribution and property of anti-beta3-adrenoceptor autoantibody in patients with heart failure].
2005 Dec
Effect of penetration enhancers on the release and skin permeation of bupranolol from reservoir-type transdermal delivery systems.
2005 Jan 20
Comparison of the alpha-adrenoceptor-mediated effects of beta3-adrenoceptor ligands in rat pulmonary artery.
2005 Jun
Adrenaline produces the relaxation of guinea-pig airway smooth muscle primarily through the mediation of beta(2)-adrenoceptors.
2005 Jun
Adrenoceptor heterogeneity in the ruminal epithelium of sheep.
2005 May
Effect of penetration enhancers on the transdermal delivery of bupranolol through rat skin.
2005 May-Jun
Positive inotropic and lusitropic effects mediated via the low-affinity state of beta1-adrenoceptors in pithed rats.
2005 Nov
Functional coupling of beta3-adrenoceptors and large conductance calcium-activated potassium channels in human uterine myocytes.
2005 Oct
Transdermal delivery of beta-blockers.
2006 May
Potential involvement of a propranolol-insensitive atypical beta-adrenoceptor the vasodilator effect of cyanopindolol in the human pulmonary artery.
2006 Sep
Nebivolol in the treatment of chronic heart failure.
2007
Effect of DL-nebivolol, its enantiomers and metabolites on the intracellular production of superoxide and nitric oxide in human endothelial cells.
2007 Apr
Is the beta3-adrenoceptor (ADRB3) a potential target for uterorelaxant drugs?
2007 Jun 1
Pharmacological characterization of the beta-adrenoceptor that mediates the relaxant response to noradrenaline in guinea-pig tracheal smooth muscle.
2007 Mar
The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder.
2007 Nov 14
GW427353 (solabegron), a novel, selective beta3-adrenergic receptor agonist, evokes bladder relaxation and increases micturition reflex threshold in the dog.
2007 Oct
Control of transdermal permeation of hydrocortisone acetate from hydrophilic and lipophilic formulations.
2008
Role of chemical structure in stereoselective recognition of beta-blockers by cyclodextrins in capillary zone electrophoresis.
2008 Apr 24
Influence of potent and selective beta-adrenoceptor agonist, CL 316243, on the contractile response of non-pregnant human myometrium.
2008 Dec
Cardiovascular effects of transdermally delivered bupranolol in rabbits: effect of chemical penetration enhancers.
2008 Jan 30
Skin permeation mechanism and bioavailability enhancement of celecoxib from transdermally applied nanoemulsion.
2008 Jul 9
beta3-adrenergic receptor activation increases human atrial tissue contractility and stimulates the L-type Ca2+ current.
2008 Sep
CGP12177-induced haemodynamic and vascular effects in normotensive and hypertensive rats.
2008 Sep 4
Comparison of the analysis of beta-blockers by different techniques.
2009 Dec 1
Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors.
2009 Mar
Beta3-adrenoceptor agonists: possible role in the treatment of overactive bladder.
2010 Dec
Pulsatile changes in free fatty acids augment hepatic glucose production and preserves peripheral glucose homeostasis.
2010 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Ophthalmic: Management of glaucoma: 0.05% to 0.5% http://cursoenarm.net/UPTODATE/contents/mobipreview.htm?19/1/19484
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 Mon Mar 31 18:36:16 GMT 2025
Edited
by admin
on Mon Mar 31 18:36:16 GMT 2025
Record UNII
858YGI5PIT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUPRANOLOL
INN   MI   WHO-DD  
INN  
Official Name English
OPHTORENIN
Preferred 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
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
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
WHO-VATC QC07AA19
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
WHO-ATC C07AA19
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
Code System Code Type Description
DRUG CENTRAL
433
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
IUPHAR
550
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
WIKIPEDIA
Bupranolol
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
CAS
14556-46-8
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
SMS_ID
100000088467
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
FDA UNII
858YGI5PIT
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
MESH
D002046
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
CAS
70578-42-6
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
SUPERSEDED
INN
3166
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
EVMPD
SUB05984MIG
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
DRUG BANK
DB08808
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
RXCUI
1817
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID7022704
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
ChEMBL
CHEMBL305380
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
PUBCHEM
2475
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
NCI_THESAURUS
C72615
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY
MERCK INDEX
m2770
Created by admin on Mon Mar 31 18:36:16 GMT 2025 , Edited by admin on Mon Mar 31 18:36:16 GMT 2025
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY