U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of BETAXOLOL

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
32.0 nM [Ki]
236.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

4.94207992E11
Primary
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

4.94207992E11
Primary
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

6.2536319E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
89.8 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
2096 μg × h/L
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
12.3 h
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

Doses

DosePopulationAdverse 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:
unhealthy, adult
Health Status: unhealthy
Condition: glaucoma
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Effects of betaxolol, a new beta 1 selective blocker, on canine ventricular arrhythmias.
1987 Feb
Comparison of the antihypertensive effects of betaxolol to atenolol.
1988 Apr 1
[Antihypertensive effects of betaxolol, a cardioselective beta-adrenoceptor antagonist, in stroke-prone spontaneously hypertensive rats (SHRSP)].
1990 Aug
Safety and compatibility of betaxolol hydrochloride combined with diltiazem or nifedipine therapy in stable angina pectoris.
1994 Feb 1
Betaxolol eye drops. A clinical trial of safety and efficacy.
1995 Feb
Ocular-specific chemical delivery systems of betaxolol for safe local treatment of glaucoma.
1997 Aug
Beta-blocker selectivity at cloned human beta 1- and beta 2-adrenergic receptors.
1999 Apr
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.
1999 Feb 19
Assessment of systemic adverse reactions induced by ophthalmic beta-adrenergic receptor antagonists.
2001 Jun
Direct enantiomeric resolution of betaxolol with application to analysis of pharmaceutical products.
2007 Feb 6
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.
2007 Oct 16
Evidence for beta1-adrenergic receptor involvement in amygdalar corticotropin-releasing factor gene expression: implications for cocaine withdrawal.
2009 Apr
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
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
INN   MI   VANDF   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:38:15 UTC 2023 , Edited by admin on Fri Dec 15 15:38:15 UTC 2023
LIVERTOX NBK548618
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WHO-VATC QS01ED02
Created by admin on Fri Dec 15 15:38:15 UTC 2023 , Edited by admin on Fri Dec 15 15:38:15 UTC 2023
WHO-ATC C07AB05
Created by admin on Fri Dec 15 15:38:15 UTC 2023 , Edited by admin on Fri Dec 15 15:38:15 UTC 2023
NDF-RT N0000000161
Created by admin on Fri Dec 15 15:38:15 UTC 2023 , Edited by admin on Fri Dec 15 15:38:15 UTC 2023
WHO-VATC QC07AB05
Created by admin on Fri Dec 15 15:38:15 UTC 2023 , Edited by admin on Fri Dec 15 15:38:15 UTC 2023
NDF-RT N0000175556
Created by admin on Fri Dec 15 15:38:15 UTC 2023 , Edited by admin on Fri Dec 15 15:38:15 UTC 2023
WHO-ATC S01ED02
Created by admin on Fri Dec 15 15:38:15 UTC 2023 , Edited by admin on Fri Dec 15 15:38:15 UTC 2023
NCI_THESAURUS C29576
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WHO-ATC S01ED52
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Code System Code Type Description
EVMPD
SUB05804MIG
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PRIMARY
INN
4530
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PRIMARY
MESH
D015784
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PRIMARY
IUPHAR
549
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PRIMARY
WIKIPEDIA
BETAXOLOL
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PRIMARY
LACTMED
Betaxolol
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PRIMARY
PUBCHEM
2369
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PRIMARY
ChEMBL
CHEMBL423
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PRIMARY
NCI_THESAURUS
C61652
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PRIMARY
FDA UNII
O0ZR1R6RZ2
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PRIMARY
MERCK INDEX
m2454
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PRIMARY Merck Index
RXCUI
1520
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PRIMARY RxNorm
CHEBI
3082
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PRIMARY
SMS_ID
100000092503
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PRIMARY
DAILYMED
O0ZR1R6RZ2
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PRIMARY
CAS
63659-18-7
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PRIMARY
DRUG CENTRAL
356
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PRIMARY
EPA CompTox
DTXSID2022674
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PRIMARY
DRUG BANK
DB00195
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PRIMARY