Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H27N5O3 |
| Molecular Weight | 373.4494 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC(=O)N1CCCN(CC1)C2=NC(N)=C3C=C(OC)C(OC)=CC3=N2
InChI
InChIKey=RHLJLALHBZGAFM-UHFFFAOYSA-N
InChI=1S/C19H27N5O3/c1-4-6-17(25)23-7-5-8-24(10-9-23)19-21-14-12-16(27-3)15(26-2)11-13(14)18(20)22-19/h11-12H,4-10H2,1-3H3,(H2,20,21,22)
| Molecular Formula | C19H27N5O3 |
| Molecular Weight | 373.4494 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
DOI: 10.1111/j.1527-3466.1988.tb00517.x | https://medikamio.com/de-de/medikamente/andante-3mg/pil | doi: 10.1016/B978-008055232-3.61351-0 | http://adisinsight.springer.com/drugs/800004823
Curator's Comment: description was created based on several sources, including:
DOI: 10.1111/j.1527-3466.1988.tb00517.x | https://medikamio.com/de-de/medikamente/andante-3mg/pil | doi: 10.1016/B978-008055232-3.61351-0 | http://adisinsight.springer.com/drugs/800004823
Bunazosin (E-643) is a quinazoline derivative with a1-adrenoceptor blocking activity. It has been clinically used both as a systemic antihypertensive as well as an ocular hypotensive drug. The major adverse effect associated with the use of bunazosin is orthostatic hypotension or its consequences (e.g. dizziness). Others adverse effects include headache, sweating, nausea, dry mouth, abdominal pain, diarrhea, and constipation. The effects of Bunazosin may be enhanced by diuretics and other antihypertensive agents and decreased by Rifampicin.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of regression of left ventricular hypertrophy following atenolol or bunazosin therapy on ischemic cardiac function and myocardial metabolism in spontaneously hypertensive rats. | 1991 Dec |
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| Orthostatic hypotension: how to avoid it during antihypertensive therapy. | 1996 Nov |
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| Noradrenaline stimulates 5-hydroxytryptamine release from mouse ileal tissues via alpha(2)-adrenoceptors. | 2001 Dec 7 |
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| Neuroprotective effect and intraocular penetration of nipradilol, a beta-blocker with nitric oxide donative action. | 2001 Mar |
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| Effect of phenylephrine injected into the nucleus tractus solitarius of Sprague-Dawley rats and spontaneously hypertensive rats. | 2002 Aug 15 |
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| Different effects of carvedilol, metoprolol, and propranolol on left ventricular remodeling after coronary stenosis or after permanent coronary occlusion in rats. | 2002 Feb 26 |
|
| Purinergic modulation of vascular sympathetic neurotransmission. | 2002 Jan |
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| The renin-angiotensin and adrenergic nervous system in cardiac hypertrophy in fructose-fed rats. | 2002 Jan |
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| Neuroprotective effects of nipradilol on purified cultured retinal ganglion cells. | 2002 Jun |
|
| The alpha(1D)-adrenergic receptor directly regulates arterial blood pressure via vasoconstriction. | 2002 Mar |
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| Amelioration by topical bunazosin hydrochloride of the impairment in ocular blood flow caused by nitric oxide synthase inhibition in rabbits. | 2003 Feb |
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| [Effects of ocular hypotensive agents on the circadian rhythm in intraocular pressure in rabbits as measured by telemetry]. | 2003 Sep |
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| Additive effect of bunazosin on intraocular pressure when topically added to treatment with latanoprost in patients with glaucoma. | 2003 Sep-Oct |
|
| Bunazosin hydrochloride reduces glutamate-induced neurotoxicity in rat primary retinal cultures. | 2004 Apr 2 |
|
| Effects of bunazosin hydrochloride on ciliary muscle constriction and matrix metalloproteinase activities. | 2004 Aug |
|
| Efficacy of bunazosin hydrochloride 0.01% as adjunctive therapy of latanoprost or timolol. | 2004 Feb |
|
| Binding affinity of bunazosin, dorzolamide, and timolol to synthetic melanin. | 2004 Jan-Feb |
|
| Ocular pharmacokinetic/ pharmacodynamic modeling for bunazosin after instillation into rabbits. | 2004 May |
|
| Effects of topically instilled bunazosin, an alpha1-adrenoceptor antagonist, on constrictions induced by phenylephrine and ET-1 in rabbit retinal arteries. | 2004 Nov |
|
| Effects of topically instilled bunazosin hydrochloride and other ocular hypotensive drugs on endothelin-1-induced constriction in rabbit retinal arteries. | 2004 Sep-Oct |
|
| Alpha1-receptor or adenosine A1-receptor dependent pathway alone is not sufficient but summation of these pathways is required to achieve an ischaemic preconditioning effect in rabbits. | 2005 Apr |
|
| Amelioration of endothelin-1-induced optic nerve head ischemia by topical bunazosin. | 2005 Feb |
|
| Evaluation of the additive effect of bunazosin on latanoprost in primary open-angle glaucoma. | 2005 Jan-Feb |
|
| alpha1-Adrenergic receptor antagonists induce production of IL-18 and expression of ICAM-1 and CD40 in human monocytes. | 2005 Jan-Feb |
|
| Alterations of alpha-adrenergic modulations of coronary microvascular tone in dogs with heart failure. | 2005 Jun |
|
| The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice. | 2005 Nov |
|
| Comparative study on the combined effects of bunazosin and nipradilol or timolol on intraocular pressure in normotensive rabbits. | 2005 Nov-Dec |
|
| Effects of different alpha-1 adrenoceptor blockers on proximal urethral function using in vivo isovolumetric pressure changes. | 2005 Oct |
|
| Bunazosin, a selective alpha1-adrenoceptor antagonist, as an anti-glaucoma drug: effects on ocular circulation and retinal neuronal damage. | 2005 Spring |
|
| Correlation between the additive effect of bunazosin and the response to latanoprost on intraocular pressure in patients with glaucoma treated with bunazosin as adjunctive therapy to latanoprost. | 2006 Jan-Feb |
|
| Local regulation of skin blood flow during cooling involving presynaptic P2 purinoceptors in rats. | 2006 Jul |
|
| An alpha1-receptor blocker reduces plasma leptin levels in hypertensive patients with obesity and hyperleptinemia. | 2006 Oct |
|
| Addition of or switch to topical bunazosin hydrochloride in elderly patients with normal-tension glaucoma: A one-year follow-up study. | 2006 Sep-Oct |
|
| Effects of adrenergic and cholinergic antagonists on diameter of nasolacrimal drainage system. | 2007 Dec |
|
| [Case of pigmentary glaucoma treated with medical therapy, laser treatment, and trabeculotomy]. | 2007 Feb |
|
| Incidence of intraoperative floppy iris syndrome in patients on either systemic or topical alpha(1)-adrenoceptor antagonist. | 2007 Jan |
|
| The IOP-lowering effects and mechanism of action of tafluprost in prostanoid receptor-deficient mice. | 2007 May |
|
| Role of alpha2C-adrenoceptors in the reduction of skin blood flow induced by local cooling in mice. | 2007 Sep |
|
| Beneficial effect of combination therapy with antihypertensive drugs in patients with hypertension. | 2007 Spring |
|
| Ocular pharmacokinetic/pharmacodynamic modeling for multiple anti-glaucoma drugs. | 2008 Aug |
|
| Possible mechanism of intraoperative floppy iris syndrome: a clinicopathological study. | 2008 Aug |
|
| Protective effects of carvedilol in murine model with the coxsackievirus B3-induced viral myocarditis. | 2008 Jan |
|
| Comparison of the cardiac electrophysiological effects between doxazosin and bunazosin. | 2008 Jul |
|
| Comparison of the cardiac effects between quinazoline-based alpha1-adrenoceptor antagonists on occlusion-reperfusion injury. | 2008 Mar |
|
| Review of nifedipine GITS in the treatment of high risk patients with coronary artery disease and hypertension. | 2009 |
|
| [The use of andante in the therapy of insomnia]. | 2009 |
|
| New perspectives of infections in cardiovascular disease. | 2009 May |
|
| Ocular hypotensive effects of anti-glaucoma agents in mice. | 2009 Oct |
|
| Distinctive effects of carvedilol in the non-infarct zone: remodelling of the ligated rat heart linked to oxidative stress. | 2009 Sep-Oct |
|
| Restraint stress induces connexin-43 translocation via α-adrenoceptors in rat heart. | 2010 Nov |
Patents
| Substance Class |
Chemical
Created
by
admin
on
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Sat Dec 16 17:06:16 GMT 2023
by
admin
on
Sat Dec 16 17:06:16 GMT 2023
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| Record UNII |
9UUW4V7G2H
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C29713
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5466
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2472
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DB12230
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DTXSID7022700
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80755-51-7
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C018176
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BUNAZOSIN
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SUB05977MIG
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C72922
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100000088446
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CHEMBL188185
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m2761
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
