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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H29NO3
Molecular Weight 307.4284
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAXOLOL, (R)-

SMILES

CC(C)NC[C@]([H])(COc1ccc(cc1)CCOCC2CC2)O

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

HIDE SMILES / InChI

Molecular Formula C18H29NO3
Molecular Weight 307.4284
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

Targets

Primary TargetPharmacologyConditionPotency
280.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BETAXOLOL HYDROCHLORIDE

Approved Use

Betaxolol hydrochloride is indicated in the management of hypertension. It may be used alone or concomitantly with other antihypertensive agents, particularly thiazide-type diuretics.

Launch Date

6.2544963E11
PubMed

PubMed

TitleDatePubMed
Does glaucoma medication influence the diameter of the retinal arteriole in the human eye? (A pilot study using the retinal vessel analyser).
2001
[Non surgical alternatives in the treatment of the primitive open angle glaucoma].
2001
Antiglaucomatous drugs effects on optic nerve head flow: design, baseline and preliminary report.
2001
[Hormone replacement therapy in women with arterial hypertension in peri- and postmenopause: hemodynamic effects].
2001
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
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
Assessment of systemic adverse reactions induced by ophthalmic beta-adrenergic receptor antagonists.
2001 Jun
Plasma concentration of topically applied betaxolol in elderly glaucoma patients.
2001 Jun
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
Effect of topical betaxolol on acute rise of aqueous flare induced by prostaglandin E(2) in pigmented rabbits.
2001 Nov-Dec
Vasorelaxant effects of racemic betaxolol and its R- and S- isomers on bovine retinal vessels.
2001 Oct
[Prospects for neuroprotective glaucoma therapy].
2001 Oct
Antiglaucoma medication and clinical depression.
2001 Oct
[Neuroprotective effect of Betoptic S-considerations after 18 months of treatment].
2002
[Evaluation of vascular risk factors in primary open-angle glaucoma using doppler sonography].
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
Delaying glaucoma.
2002 Dec
To treat or not to treat? That is the question.
2002 Dec
A double-masked randomized comparison of the efficacy and safety of unoprostone with timolol and betaxolol in patients with primary open-angle glaucoma including pseudoexfoliation glaucoma or ocular hypertension. 6 month data.
2002 Jan
Autoantibody against neuron-specific enolase found in glaucoma patients causes retinal dysfunction in vivo.
2002 Jan-Feb
Effect of topical betaxolol on the acute rise of aqueous flare induced by highly selective agonists for prostaglandin E2 receptor subtypes in pigmented rabbits.
2002 Jan-Feb
Ocular drug delivery using 20-kHz ultrasound.
2002 Jun
Positive use test in contact dermatitis from betaxolol hydrochloride.
2002 May
Topical flunarizine reduces IOP and protects the retina against ischemia-excitotoxicity.
2002 May
Determination of betaxolol in human aqueous humour by high-performance liquid chromatography with fluorescence detection.
2002 May 25
Ocular surface changes induced by topical antiglaucoma monotherapy.
2002 May-Jun
Effect of betaxolol on aspartate aminotransferase activity in hypoxic rat retina in vitro.
2002 Oct
Effect of beta-adrenoceptor antagonists on autonomic control of ciliary smooth muscle.
2002 Sep
Generation and analysis of constitutively active and physically destabilized mutants of the human beta(1)-adrenoceptor.
2002 Sep
[Betaxolol for prevention of steroid induced intraocular pressure elevations in patients after radial keratotomy].
2003
The beta-adrenoceptor antagonists metipranolol and timolol are retinal neuroprotectants: comparison with betaxolol.
2003 Apr
Betaxolol-induced deterioration of asthma and a pharmacodynamic analysis based on beta-receptor occupancy.
2003 Aug
Randomized clinical trial of topical betaxolol for persistent macular edema after vitrectomy and epiretinal membrane removal.
2003 Aug
Betaxolol improves the survival rate and changes natriuretic peptide expression in rats with heart failure.
2003 Jan
Effects of the beta1-selective adrenergic antagonist betaxolol on electroretinography in the perfused cat eye.
2003 Jan
Atrial fibrillation in chronic dialysis patients in the United States: risk factors for hospitalization and mortality.
2003 Jan 24
Patient persistency with pharmacotherapy in the management of glaucoma.
2003 Jul
Medical therapy cost considerations for glaucoma.
2003 Jul
Role of epinephrine stimulation of CNS alpha1-adrenoceptors in motor activity in mice.
2003 Jul
Changing antiglaucoma therapy from timolol to betaxolol: effect on ocular blood flow.
2003 Jul-Aug
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
Iganidipine, a new water-soluble Ca2+ antagonist: ocular and periocular penetration after instillation.
2003 Mar
Beneficial effects of betaxolol, a selective antagonist of beta-1 adrenoceptors, on exercise-induced myocardial ischemia in patients with coronary vasospasm.
2003 Oct
Betaxolol attenuates retinal ischemia/reperfusion damage in the rat.
2003 Oct 27
Inner retinal neurons display differential responses to N-methyl-D-aspartate receptor activation.
2003 Oct 6
Discriminative stimulus properties of antidepressant agents: a review.
2003 Sep
Patents

Sample Use Guides

In Vivo Use Guide
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
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
by admin
on Sat Jun 26 07:02:59 UTC 2021
Edited
by admin
on Sat Jun 26 07:02:59 UTC 2021
Record UNII
759O83814X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETAXOLOL, (R)-
Common Name English
2-PROPANOL, 1-(4-(2-(CYCLOPROPYLMETHOXY)ETHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-, (2R)-
Systematic Name English
BETAXOLOL, (+)-
Common Name English
Code System Code Type Description
FDA UNII
759O83814X
Created by admin on Sat Jun 26 07:02:59 UTC 2021 , Edited by admin on Sat Jun 26 07:02:59 UTC 2021
PRIMARY
CAS
91878-53-4
Created by admin on Sat Jun 26 07:02:59 UTC 2021 , Edited by admin on Sat Jun 26 07:02:59 UTC 2021
PRIMARY
PUBCHEM
6093355
Created by admin on Sat Jun 26 07:02:59 UTC 2021 , Edited by admin on Sat Jun 26 07:02:59 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER