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
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
| 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
| Title | Date | PubMed |
|---|---|---|
| [Betamed in the treatment of psychogenic disorders with a somatic component]. | 1983 Sep 30 |
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| Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor. | 1993 Dec |
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| Carazolol: a potent, selective beta 3-adrenoceptor agonist. | 1995 Nov 30 |
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| Potent and selective human beta(3)-adrenergic receptor antagonists. | 1999 Aug |
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| LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors. | 1999 Feb 19 |
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| (+/-)-Pindolol acts as a partial agonist at atypical beta-adrenoceptors in the guinea pig duodenum. | 2001 Jan |
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| Functional properties of atypical beta-adrenoceptors on the guinea pig duodenum. | 2001 Mar 23 |
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| Upregulation of functional beta(3)-adrenergic receptor in the failing canine myocardium. | 2001 Sep 28 |
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| The beta2- and beta3-adrenoceptor-mediated relaxation induced by fenoterol in guinea pig taenia caecum. | 2002 Oct |
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| Characterization of adrenoceptor involvement in skeletal and cardiac myotoxicity Induced by sympathomimetic agents: toward a new bioassay for beta-blockers. | 2003 Apr |
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| Atypical cardiostimulant beta-adrenoceptor in the rat heart: stereoselective antagonism by bupranolol but lack of effect by some bupranolol analogues. | 2003 Aug |
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| Pharmacological evidence for beta3 adrenoceptors in the control of rat gastric acid secretion. | 2003 Feb |
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| [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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Effect of penetration enhancers on the transdermal delivery of bupranolol through rat skin. | 2005 May-Jun |
|
| Transdermal delivery of beta-blockers. | 2006 May |
|
| Effect of DL-nebivolol, its enantiomers and metabolites on the intracellular production of superoxide and nitric oxide in human endothelial cells. | 2007 Apr |
|
| 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 |
|
| 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 |
|
| 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 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
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| Record UNII |
858YGI5PIT
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Validated (UNII)
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C29576
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QC07AA19
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WHO-ATC |
C07AA19
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433
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550
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Bupranolol
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100000088467
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858YGI5PIT
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D002046
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SUB05984MIG
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DTXSID7022704
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CHEMBL305380
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2475
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C72615
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M2770
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ACTIVE MOIETY |
