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

Details

Stereochemistry RACEMIC
Molecular Formula C18H29NO3.ClH
Molecular Weight 343.8893
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAXOLOL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=CHDPSNLJFOQTRK-UHFFFAOYSA-N
InChI=1S/C18H29NO3.ClH/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;1H

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
[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
Antiglaucoma medication and clinical depression.
2001 Oct
Betaxolol improves the survival rate and changes natriuretic peptide expression in rats with heart failure.
2003 Jan
Beneficial effects of betaxolol, a selective antagonist of beta-1 adrenoceptors, on exercise-induced myocardial ischemia in patients with coronary vasospasm.
2003 Oct
The comparative cardiovascular, pulmonary, ocular blood flow, and ocular hypotensive effects of topical travoprost, bimatoprost, brimonidine, and betaxolol.
2004 Aug
Beta-adrenergic stimulation induces interleukin-18 expression via beta2-AR, PI3K, Akt, IKK, and NF-kappaB.
2004 Jun 25
Direct enantiomeric resolution of betaxolol with application to analysis of pharmaceutical products.
2007 Feb 6
Betaxolol, a selective beta(1)-adrenergic receptor antagonist, diminishes anxiety-like behavior during early withdrawal from chronic cocaine administration in rats.
2007 Jun 30
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
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 Fri Jun 25 21:02:08 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:08 UTC 2021
Record UNII
6X97D2XT0O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETAXOLOL HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
BETAXOLOL HYDROCHLORIDE [WHO-DD]
Common Name English
BETAXOLOL HYDROCHLORIDE [VANDF]
Common Name English
BETAXOLOL HYDROCHLORIDE COMPONENT OF BETOPTIC PILO
Common Name English
KERLEDEX COMPONENT BETAXOLOL HYDROCHLORIDE
Common Name English
BETAXOLOL HYDROCHLORIDE [MART.]
Common Name English
BETOPTIC PILO COMPONENT BETAXOLOL HYDROCHLORIDE
Common Name English
KERLONE
Brand Name English
BETAXOLOL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
BETAXOLOL HYDROCHLORIDE [MI]
Common Name English
BETAXOLOL HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
BETAXOLOL HYDROCHLORIDE COMPONENT OF KERLEDEX
Common Name English
ALO-140102
Code English
BETAXOLOL HYDROCHLORIDE [USP-RS]
Common Name English
(+/-)-1-(P-(2-(CYCLOPROPYLMETHOXY)ETHYL)PHENOXY)-3-(ISOPROPYLAMINO)-2-PROPANOL HYDROCHLORIDE
Systematic Name English
SL-75.212-10
Code English
BETAXOLOL HYDROCHLORIDE [JAN]
Common Name English
SL-7521210
Code English
BETAXOLOL HCL
Common Name English
ALO-1401-02
Code English
BETOPTIC
Brand Name English
NSC-760048
Code English
2-PROPANOL, 1-(4-(2-(CYCLOPROPYLMETHOXY)ETHYL)PHENOXY)-3-((1-METHYLETHYL)AMINO)-, HYDROCHLORIDE, (+/-)-
Systematic Name English
BETAXOLOL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
BETAXOLOL HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
NCI_THESAURUS C29705
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL423
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY
USP_CATALOG
1069903
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY USP-RS
EVMPD
SUB13062MIG
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY
FDA UNII
6X97D2XT0O
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY
DRUG BANK
DBSALT000328
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY
PUBCHEM
107952
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY
NCI_THESAURUS
C47413
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
264-384-3
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY
CAS
63659-19-8
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY
RXCUI
142144
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M2454
Created by admin on Fri Jun 25 21:02:08 UTC 2021 , Edited by admin on Fri Jun 25 21:02:08 UTC 2021
PRIMARY Merck Index
Related Record Type Details
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY