Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C18H29NO3 |
Molecular Weight | 307.4278 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NC[C@@H](O)COC1=CC=C(CCOCC2CC2)C=C1
InChI
InChIKey=NWIUTZDMDHAVTP-QGZVFWFLSA-N
InChI=1S/C18H29NO3/c1-14(2)19-11-17(20)13-22-18-7-5-15(6-8-18)9-10-21-12-16-3-4-16/h5-8,14,16-17,19-20H,3-4,9-13H2,1-2H3/t17-/m1/s1
Molecular Formula | C18H29NO3 |
Molecular Weight | 307.4278 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Betaxolol is a competitive, beta(1)-selective (cardioselective) adrenergic antagonist. Betaxolol is used to treat hypertension, arrhythmias, coronary heart disease, glaucoma, and is also used to reduce non-fatal cardiac events in patients with heart failure. (R)-Betaxolol (Dextrobetaxolol) is the R-isomer of Betaxolol (B328000), a cardioselective β1-adrenergic blocker. It is also an antihypertensive and antiglaucoma agent. Dextrobetaxolol had a much weaker affinity at both b1 and b2 receptors than levobetaxolol. Levobetaxolol (Kb=6 nM at b1 and Kb=39 nM at b2 receptors) more potently inhibited functional activities in cells expressing human recombinant b1 and b2 receptors than
dextrobetaxolol (Kb=350 and 278 nM, respectively). Likewise, levobetaxolol was a more potent antagonist in isolated tissues than dextrobetaxolol. In functional assays in cultured human NPE cells levobetaxolol (Ki =16.4 nM) was a potent antagonist of isoproterenol-induced cAMP production with dextrobetaxolol (Ki =2.9 uM) being considerably weaker than the latter antagonist. In ocular hypertensive cynomolgus monkeys, levobetaxolol was more effective at reducing IOP than dextrobetaxolol. The results of the study of the pharmacokinetic behavior of the R and S enantiomers of betaxolol following iv and oral administration of the racemate to healthy male subjects failed to reveal any important difference between the pharmacokinetics of the R and S enantiomer of betaxolol. Thus, the pharmacokinetic behavior of racemic betaxolol accurately reflects the behavior of betaxolol enantiomers in this subject group.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11572462 |
280.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BETAXOLOL HYDROCHLORIDE Approved UseBetaxolol hydrochloride is indicated in the management of hypertension. It may be used alone or
concomitantly with other antihypertensive agents, particularly thiazide-type diuretics. Launch Date6.2544963E11 |
PubMed
Title | Date | PubMed |
---|---|---|
Levobetaxolol (Betaxon): in vitro pharmacology, intraocular pressure lowering activity and autoradiographic localization of beta-adrenoceptors in human eyes. | 2001 |
|
[Hormone replacement therapy in women with arterial hypertension in peri- and postmenopause: hemodynamic effects]. | 2001 |
|
Levobetaxolol (Betaxon) and other beta-adrenergic antagonists: preclinical pharmacology, IOP-lowering activity and sites of action in human eyes. | 2001 Aug |
|
Comparison of the effects of isoproterenol administered into the hippocampus, frontal cortex, or amygdala on behavior of rats maintained by differential reinforcement of low response rate. | 2001 Dec |
|
Ocular and retrobulbar blood flow in ocular hypertensives treated with topical timolol, betaxolol and carteolol. | 2001 Dec |
|
Contact dermatitis to topical drugs for glaucoma. | 2001 Dec |
|
The effects of beta-blockers on ocular blood flow in patients with primary open angle glaucoma: a color Doppler imaging study. | 2001 Jan-Mar |
|
Comparative effects of antiglaucoma drugs on voltage-dependent calcium channels. | 2001 Jul |
|
Comparison of the clinical success and quality-of-life impact of brimonidine 0.2% and betaxolol 0.25 % suspension in patients with elevated intraocular pressure. | 2001 Jul |
|
[Additive effects of topical carbonic anhydrase inhibitors]. | 2001 Jul |
|
Plasma concentration of topically applied betaxolol in elderly glaucoma patients. | 2001 Jun |
|
Beta-adrenergic cardiac hypertrophy is mediated primarily by the beta(1)-subtype in the rat heart. | 2001 Mar |
|
Cardiovascular considerations in using topical, oral, and intravenous drugs for the treatment of glaucoma and ocular hypertension: focus on beta-adrenergic blockade. | 2001 Nov-Dec |
|
Short-term effect of beta-adrenoreceptor blocking agents on ocular blood flow. | 2001 Oct |
|
[Prospects for neuroprotective glaucoma therapy]. | 2001 Oct |
|
Chiral separation of beta-blockers after derivatization with (-)-alphamethoxy-alpha-(trifluoromethyl)phenylacetyl chloride by gas chromatography. | 2001 Oct |
|
Late normalization of melanocytomalytic intraocular pressure elevation following excision of iris melanocytoma. | 2001 Sep |
|
[Autonomic nervous system function and effects of beta-adrenoblockers on heart rhythm variability in patients with myocardial infarction]. | 2002 |
|
Safety of unoprostone isopropyl as mono- or adjunctive therapy in patients with primary open-angle glaucoma or ocular hypertension. | 2002 |
|
Comparison of the neuroprotective effects of adrenoceptor drugs in retinal cell culture and intact retina. | 2002 Aug |
|
Effects of antidepressants in rats trained to discriminate centrally administered isoproterenol. | 2002 Aug |
|
Effect of betaxolol on impaired choroidal blood flow after intravitreal injection of endothelin-1 in albino rabbits. | 2002 Jun |
|
Nonselective Beta-adrenergic blockade augments fasting hyperkalemia in hemodialysis patients. | 2002 Jun |
|
[Human trabecular cells and apoptosis: in vitro evaluation of the effect of betaxolol with or without preservative]. | 2002 Oct |
|
Effect of betaxolol on aspartate aminotransferase activity in hypoxic rat retina in vitro. | 2002 Oct |
|
Progression of retinal nerve fibre layer damage in betaxolol- and timolol-treated glaucoma patients. | 2002 Oct |
|
Expectations from clinical trials: results of the Early Manifest Glaucoma Trial. | 2002 Oct |
|
Effect of treatment by medicine or surgery on intraocular pressure and pulsatile ocular blood flow in normal-pressure glaucoma. | 2002 Sep |
|
Nitric oxide synthase expression in the transient ischemic rat retina: neuroprotection of betaxolol. | 2002 Sep 27 |
|
Effects of beta-adrenergic blockers on glutamate-induced calcium signals in adult mouse retinal ganglion cells. | 2003 Jan 3 |
|
Effects of commercial antiglaucoma drugs to glutamate-induced [Ca2+)]i increase in cultured neuroblastoma cells. | 2003 Jun |
|
Activation of beta1-adrenoceptors excites striatal cholinergic interneurons through a cAMP-dependent, protein kinase-independent pathway. | 2003 Jun 15 |
|
Results of the betaxolol versus placebo treatment trial in ocular hypertension. | 2003 Mar |
|
Change in endothelial nitric oxide synthase in the rat retina following transient ischemia. | 2003 Mar 3 |
|
Effects of betaxolol and flunarizine on visual fields and intraocular pressure in patients with migraine. | 2003 May |
|
Beneficial effects of betaxolol, a selective antagonist of beta-1 adrenoceptors, on exercise-induced myocardial ischemia in patients with coronary vasospasm. | 2003 Oct |
|
Discriminative stimulus properties of antidepressant agents: a review. | 2003 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ppa/betaxolol-systemic.html
Curator's Comment: Topical use: in ocular hypertensive cynomolgus monkeys, levobetaxolol was more effective at reducing IOP than (R)-Betaxolol (Dextrobetaxolol). In a crossover study, a single dose of 150 mg/eye of levobetaxolol reduced IOP by a maximum of 25.9% whereas the same dose of dextrobetaxolol reduced IOP by only 15.5%.
Hypertension: Oral: Initial: 10 mg once daily; may increase dose to 20 mg daily after 7 to 14 days if desired response is not achieved. Increasing the dose beyond 20 mg daily has not been shown to produce further antihypertensive effect.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11572462
Levobetaxolol (Kb=6 nM at b1 and Kb=39 nM at b2 receptors) more potently inhibited functional activities in cells expressing human recombinant b1 and b2 receptors than dextrobetaxolol (Kb=350 and 278 nM, respectively). In functional assays in cultured human NPE cells levobetaxolol (Ki =16.4 nM) was a potent antagonist of isoproterenol-induced cAMP production with dextrobetaxolol (Ki =2.9 uM) being considerably weaker than the latter antagonist.
Substance Class |
Chemical
Created
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Edited
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Record UNII |
759O83814X
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Record Status |
Validated (UNII)
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Record Version |
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Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER |