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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

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
Nebivolol induces calcium-independent signaling in endothelial cells by a possible beta-adrenergic pathway.
2001 Aug
Cardiovascular effects of beta 3-adrenoceptor stimulation in perinephritic hypertension.
2001 Aug
Upregulation of functional beta(3)-adrenergic receptor in the failing canine myocardium.
2001 Sep 28
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
The beta2- and beta3-adrenoceptor-mediated relaxation induced by fenoterol in guinea pig taenia caecum.
2002 Oct
Orthovanadate decreases the leptin content in isolated mouse fat pads via proteasome activation.
2002 Oct 15
Beta2- and beta3-adrenoreceptor agonists: human myometrial selectivity and effects on umbilical artery tone.
2002 Sep
beta3-Adrenergic stimulation produces a decrease of cardiac contractility ex vivo in mice overexpressing the human beta3-adrenergic receptor.
2003 Aug 1
Burst-like control of lipolysis by the sympathetic nervous system in vivo.
2003 Jan
[Impairment of atypical beta-adrenergic-mediated relaxation in spontaneously hypertensive rats before and during the development of arterial hypertension].
2003 Jul-Aug
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
Overexpression of beta 1-adrenoceptors in adult rat ventricular myocytes enhances CGP 12177A cardiostimulation: implications for 'putative' beta 4-adrenoceptor pharmacology.
2004 Mar
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.
2004 May
Inconsistent role of nitric oxide on lipolysis in isolated rat adipocytes.
2005
Adrenoceptor heterogeneity in the ruminal epithelium of sheep.
2005 May
Positive inotropic and lusitropic effects mediated via the low-affinity state of beta1-adrenoceptors in pithed rats.
2005 Nov
Nebivolol in the treatment of chronic heart failure.
2007
Pharmacological characterization of the beta-adrenoceptor that mediates the relaxant response to noradrenaline in guinea-pig tracheal smooth muscle.
2007 Mar
Role of chemical structure in stereoselective recognition of beta-blockers by cyclodextrins in capillary zone electrophoresis.
2008 Apr 24
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
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 Fri Dec 15 16:47:17 GMT 2023
Edited
by admin
on Fri Dec 15 16:47:17 GMT 2023
Record UNII
858YGI5PIT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUPRANOLOL
INN   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
WHO-VATC QC07AA19
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
WHO-ATC C07AA19
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
Code System Code Type Description
DRUG CENTRAL
433
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
IUPHAR
550
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
WIKIPEDIA
Bupranolol
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
CAS
14556-46-8
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
SMS_ID
100000088467
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
FDA UNII
858YGI5PIT
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
MESH
D002046
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
CAS
70578-42-6
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
SUPERSEDED
INN
3166
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
EVMPD
SUB05984MIG
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
DRUG BANK
DB08808
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
RXCUI
1817
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID7022704
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL305380
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
PUBCHEM
2475
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
NCI_THESAURUS
C72615
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY
MERCK INDEX
m2770
Created by admin on Fri Dec 15 16:47:17 GMT 2023 , Edited by admin on Fri Dec 15 16:47:17 GMT 2023
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY