BETAXOLOL

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

Structure Search

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

HIDE SMILES / InChI

Description
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
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10372227	Antagonist 2778		32.0 nM [Ki]
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10372227	Antagonist 2778		236.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Ocular hypertension 50 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2202584	Primary	Approved 8429	BETOPTIC Approved Use Betaxolol 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 Date 1985
Open-angle glaucoma 51 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2202584	Primary	Approved 8429	BETOPTIC Approved Use Betaxolol 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 Date 1985
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2866947	Primary	Approved 8429	KERLONE Approved Use Kerlone is indicated in the management of hypertension. It may be used alone or concomitantly with other antihypertensive agents, particularly thiazide-type diuretics. Launch Date 1989

C_max

Value	Dose	Co-administered	Analyte	Population
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	Analyte	Population
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

T_1/2

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

Doses

Dose	Population	Adverse events
0.5 % 2 times / day steady, ophthalmic Recommended Dose: 0.5 %, 2 times / day Route: ophthalmic Route: steady Dose: 0.5 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19270s031lbl.pdf	unhealthy, adult Health Status: unhealthy Condition: glaucoma Age Group: adult Sex: unknown Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19270s031lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/19270s031lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Ca2+ channels 57 L-type Ca2+ channels 28

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Ca2+ channels 60	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17180523/; https://pubmed.ncbi.nlm.nih.gov/10870519/	yes
L-type Ca2+ channels 30	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10493108/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3082	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3082
ChemicalBook	CB1134548	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1134548
MolPort	MolPort-003-845-027	https://www.molport.com/shop/molecule-link/MolPort-003-845-027
Selleck Chemicals	betaxolol-betoptic	http://www.selleckchem.com/products/betaxolol-betoptic.html

PubMed

Title	Date	PubMed
Comparison of the antihypertensive effects of betaxolol to atenolol.	1988 Apr 1	2895577
[Antihypertensive effects of betaxolol, a cardioselective beta-adrenoceptor antagonist, in stroke-prone spontaneously hypertensive rats (SHRSP)].	1990 Aug	1977670
Safety and compatibility of betaxolol hydrochloride combined with diltiazem or nifedipine therapy in stable angina pectoris.	1994 Feb 1	8296748
Betaxolol eye drops. A clinical trial of safety and efficacy.	1995 Feb	7619450
Ocular-specific chemical delivery systems of betaxolol for safe local treatment of glaucoma.	1997 Aug	9342554
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.	1999 Feb 19	10079020
Assessment of systemic adverse reactions induced by ophthalmic beta-adrenergic receptor antagonists.	2001 Jun	11436944
Beneficial effects of betaxolol, a selective antagonist of beta-1 adrenoceptors, on exercise-induced myocardial ischemia in patients with coronary vasospasm.	2003 Oct	14559135
The comparative cardiovascular, pulmonary, ocular blood flow, and ocular hypotensive effects of topical travoprost, bimatoprost, brimonidine, and betaxolol.	2004 Aug	15321024
Betaxolol, a selective beta(1)-adrenergic receptor antagonist, diminishes anxiety-like behavior during early withdrawal from chronic cocaine administration in rats.	2007 Jun 30	17513029
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.	2007 Oct 16	17925438

Patents

Sample Use Guides

In Vivo Use Guide

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

Betaxolol (162 microM, 16.2 microM, and 1.62 microM) induced a significant increase in [Ca2+]i in cultured corneal endothelial cells

Name

Type

Language

BETAXOLOL

Official Name

English

2-PROPANOL, 1-(4-(2-(CYCLOPROPYLMETHOXY)ETHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-

Systematic Name

English

betaxolol [INN]

Common Name

English

SL-7521210 FREE BASE

Code

English

BETAXOLOL [MI]

Common Name

English

ALO-140102 FREE BASE

Code

English

Betaxolol [WHO-DD]

Common Name

English

BETAXOLOL [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QS01ED52