Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H29NO3 |
Molecular Weight | 307.4278 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)NCC(O)COC1=CC=C(CCOCC2CC2)C=C1
InChI
InChIKey=NWIUTZDMDHAVTP-UHFFFAOYSA-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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/43176Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10372227 | https://www.ncbi.nlm.nih.gov/pubmed/2866947 | https://www.ncbi.nlm.nih.gov/pubmed/2202584
Sources: https://www.ncbi.nlm.nih.gov/pubmed/43176
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10372227 | https://www.ncbi.nlm.nih.gov/pubmed/2866947 | https://www.ncbi.nlm.nih.gov/pubmed/2202584
Betaxolol or SL 75212, (± )-1-(isopropylamino)-3-(p-(cyclopropylmethoxyethyl-phenoxy)2-propranol, is a potent cardioselective beta1-adrenoceptor antagonist
devoid of intrinsic sympathomimetic activity with very weak local anaesthetic properties. Oral betaxolol has been used for the treatment of essential hypertension. Betaxolol is used topically in glaucoma and ocular hypertension.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10372227 |
32.0 nM [Ki] | ||
Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10372227 |
236.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | BETOPTIC Approved UseBetaxolol Ophthalmic Solution has been shown to be effective in lowering intraocular pressure and is indicated in the treatment of ocular hypertension and chronic open-angle glaucoma. It may be used alone or in combination with other anti-glaucoma drugs. In clinical studies, betaxolol ophthalmic solution was safely used to lower intraocular pressure in 47 patients with both glaucoma and reactive airway disease who were followed for a mean period of 15 months. However, caution should be used in treating patients with severe reactive airway disease or a history of asthma. Launch Date4.94207992E11 |
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Primary | BETOPTIC Approved UseBetaxolol Ophthalmic Solution has been shown to be effective in lowering intraocular pressure and is indicated in the treatment of ocular hypertension and chronic open-angle glaucoma. It may be used alone or in combination with other anti-glaucoma drugs. In clinical studies, betaxolol ophthalmic solution was safely used to lower intraocular pressure in 47 patients with both glaucoma and reactive airway disease who were followed for a mean period of 15 months. However, caution should be used in treating patients with severe reactive airway disease or a history of asthma. Launch Date4.94207992E11 |
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Primary | KERLONE Approved UseKerlone is indicated in the management of hypertension. It may be used alone or concomitantly with other antihypertensive agents, particularly thiazide-type diuretics. Launch Date6.2536319E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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89.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1865331 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
BETAXOLOL blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
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2096 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1865331 |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
BETAXOLOL blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
610 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1865331 |
10 mg single, intravenous dose: 10 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
BETAXOLOL blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
971.11 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6104973 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
BETAXOLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6104973 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
BETAXOLOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
PubMed
Title | Date | PubMed |
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Effects of betaxolol, a new beta 1 selective blocker, on canine ventricular arrhythmias. | 1987 Feb |
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Comparison of the antihypertensive effects of betaxolol to atenolol. | 1988 Apr 1 |
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[Antihypertensive effects of betaxolol, a cardioselective beta-adrenoceptor antagonist, in stroke-prone spontaneously hypertensive rats (SHRSP)]. | 1990 Aug |
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Safety and compatibility of betaxolol hydrochloride combined with diltiazem or nifedipine therapy in stable angina pectoris. | 1994 Feb 1 |
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Betaxolol eye drops. A clinical trial of safety and efficacy. | 1995 Feb |
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Ocular-specific chemical delivery systems of betaxolol for safe local treatment of glaucoma. | 1997 Aug |
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Beta-blocker selectivity at cloned human beta 1- and beta 2-adrenergic receptors. | 1999 Apr |
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LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors. | 1999 Feb 19 |
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Assessment of systemic adverse reactions induced by ophthalmic beta-adrenergic receptor antagonists. | 2001 Jun |
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Antiglaucoma medication and clinical depression. | 2001 Oct |
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Betaxolol improves the survival rate and changes natriuretic peptide expression in rats with heart failure. | 2003 Jan |
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Beneficial effects of betaxolol, a selective antagonist of beta-1 adrenoceptors, on exercise-induced myocardial ischemia in patients with coronary vasospasm. | 2003 Oct |
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The comparative cardiovascular, pulmonary, ocular blood flow, and ocular hypotensive effects of topical travoprost, bimatoprost, brimonidine, and betaxolol. | 2004 Aug |
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Beta-adrenergic stimulation induces interleukin-18 expression via beta2-AR, PI3K, Akt, IKK, and NF-kappaB. | 2004 Jun 25 |
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Direct enantiomeric resolution of betaxolol with application to analysis of pharmaceutical products. | 2007 Feb 6 |
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Betaxolol, a selective beta(1)-adrenergic receptor antagonist, diminishes anxiety-like behavior during early withdrawal from chronic cocaine administration in rats. | 2007 Jun 30 |
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A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. | 2007 Oct 16 |
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Evidence for beta1-adrenergic receptor involvement in amygdalar corticotropin-releasing factor gene expression: implications for cocaine withdrawal. | 2009 Apr |
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The structure of betaxolol studied by infrared spectroscopy and natural bond orbital theory. | 2010 Aug |
Patents
Sample Use Guides
The initial dose of Kerlone (betaxolol hydrochloride tablets) in hypertension is ordinarily 10 mg once daily either alone or added to diuretic therapy. The full antihypertensive effect is usually seen within 7 to 14 days. If the desired response is not achieved the dose can be doubled after 7 to 14 days. Increasing the dose beyond 20 mg has not been shown to produce a statistically significant additional antihypertensive effect; but the 40-mg dose has been studied and is well tolerated. An increased effect (reduction) on heart rate should be anticipated with increasing dosage. If monotherapy with Kerlone does not produce the desired response, the addition of a diuretic agent or other antihypertensive should be considered.
The usual dose is one drop of BETOPTIC® (betaxolol hydrochloride) Eye Drops 0.5% or BETOPTIC S Eye Drops 0.25% in the affected eye(s) twice daily. In some patients, the intraocular pressure lowering response to BETOPTIC Eye Drops 0.5% or BETOPTIC S Eye Drops 0.25% may require a few weeks to stabilise. Clinical follow up should include a determination of the intraocular pressure during the first month of treatment with BETOPTIC Eye Drops 0.5% or BETOPTIC S Eye Drops 0.25%. Thereafter, intraocular pressure should be determined on an individual basis at the judgement of the physician.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16568722
Betaxolol (162 microM, 16.2 microM, and 1.62 microM) induced a significant increase in [Ca2+]i in cultured corneal endothelial cells
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NBK548618
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C07AB05
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S01ED02
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C29576
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S01ED52
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BETAXOLOL
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Betaxolol
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)