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
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
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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| Assessment of beta-blocking activity of low-dose bupranolol. | 1989 |
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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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| 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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| beta3-Adrenergic stimulation produces a decrease of cardiac contractility ex vivo in mice overexpressing the human beta3-adrenergic receptor. | 2003 Aug 1 |
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| Comparison between CL-316243- and CGP-12177A-induced relaxations in isolated canine ureter. | 2003 Jul |
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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 |
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| The beta3-adrenoceptor-mediated relaxation induced by dopamine in guinea pig taenia caecum. | 2003 Jun |
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| Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor. | 2003 Jun |
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| [Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications]. | 2003 Oct-Dec |
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| 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 |
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| 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 |
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| Transdermal delivery of beta-blockers. | 2006 May |
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| Potential involvement of a propranolol-insensitive atypical beta-adrenoceptor the vasodilator effect of cyanopindolol in the human pulmonary artery. | 2006 Sep |
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| Nebivolol in the treatment of chronic heart failure. | 2007 |
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| Effect of DL-nebivolol, its enantiomers and metabolites on the intracellular production of superoxide and nitric oxide in human endothelial cells. | 2007 Apr |
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| Is the beta3-adrenoceptor (ADRB3) a potential target for uterorelaxant drugs? | 2007 Jun 1 |
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| Pharmacological characterization of the beta-adrenoceptor that mediates the relaxant response to noradrenaline in guinea-pig tracheal smooth muscle. | 2007 Mar |
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| The effects and selectivity of beta-adrenoceptor agonists in rat myometrium and urinary bladder. | 2007 Nov 14 |
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| GW427353 (solabegron), a novel, selective beta3-adrenergic receptor agonist, evokes bladder relaxation and increases micturition reflex threshold in the dog. | 2007 Oct |
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| 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 |
|
| Impairment of NO-dependent relaxation in intralobar pulmonary arteries: comparison of urban particulate matter and manufactured nanoparticles. | 2008 Oct |
|
| 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 |
|
| Amphiphilic poly{[alpha-maleic anhydride-omega-methoxy-poly(ethylene glycol)]-co-(ethyl cyanoacrylate)} graft copolymer nanoparticles as carriers for transdermal drug delivery. | 2009 |
|
| 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 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
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DTC2G3GDPL
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100000084855
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DBSALT000905
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236806
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239-208-3
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15148-80-8
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m2770
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27072
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SUB00903MIG
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ACTIVE MOIETY
SUBSTANCE RECORD
