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Details

Stereochemistry RACEMIC
Molecular Formula C18H29NO3
Molecular Weight 307.4284
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAXOLOL

SMILES

CC(C)NCC(COc1ccc(cc1)CCOCC2CC2)O

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

Molecular Formula C18H29NO3
Molecular Weight 307.4284
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
[Antihypertensive effects of betaxolol, a cardioselective beta-adrenoceptor antagonist, in stroke-prone spontaneously hypertensive rats (SHRSP)].
1990 Aug
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.
1999 Feb 19
Betaxolol improves the survival rate and changes natriuretic peptide expression in rats with heart failure.
2003 Jan
A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling.
2007 Oct 16
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:02:33 UTC 2021
Edited
by admin
on Sat Jun 26 07:02:33 UTC 2021
Record UNII
O0ZR1R6RZ2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETAXOLOL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BETAXOLOL [WHO-DD]
Common 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 [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QS01ED52
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
LIVERTOX 101
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
WHO-VATC QS01ED02
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
WHO-ATC C07AB05
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
NDF-RT N0000000161
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
WHO-VATC QC07AB05
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
NDF-RT N0000175556
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
WHO-ATC S01ED02
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
WHO-ATC S01ED52
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
Code System Code Type Description
EVMPD
SUB05804MIG
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
INN
4530
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
MESH
D015784
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
IUPHAR
549
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
WIKIPEDIA
BETAXOLOL
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
LACTMED
Betaxolol
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
PUBCHEM
2369
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
ChEMBL
CHEMBL423
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
NCI_THESAURUS
C61652
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
FDA UNII
O0ZR1R6RZ2
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
MERCK INDEX
M2454
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY Merck Index
RXCUI
1520
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY RxNorm
CAS
63659-18-7
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
DRUG CENTRAL
356
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
EPA CompTox
63659-18-7
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
DRUG BANK
DB00195
Created by admin on Sat Jun 26 07:02:34 UTC 2021 , Edited by admin on Sat Jun 26 07:02:34 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
ENANTIOMER -> RACEMATE
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC