LEVOBETAXOLOL HYDROCHLORIDE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H29NO3.ClH
Molecular Weight	343.889
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LEVOBETAXOLOL HYDROCHLORIDE

Structure Search

SMILES

Cl.CC(C)NC[C@H](O)COC1=CC=C(CCOCC2CC2)C=C1

InChI

InChIKey=CHDPSNLJFOQTRK-LMOVPXPDSA-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/t17-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H29NO3
Molecular Weight	307.4278
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19668496
Curator's Comment: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021114s003lbl.pdf

BETAXON™ is a trade name for levobetaxolol hydrochloride ophthalmic suspension 0.5%, which is indicated for lowering intraocular pressure in patients with chronic open-angle glaucoma or ocular hypertension. The brand name Betaxon is discontinued in USA, but generic versions may be available. Levobetaxolol is a cardioselective (beta-1¬ adrenergic) receptor-blocking agent that does not have significant membrane-stabilizing (local anesthetic) activity and is devoid of intrinsic sympathomimetic action. Animal studies suggest levobetaxolol (S-isomer) is the more active enantiomer of betaxolol (racemate).

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/19668496	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Open-angle glaucoma 51 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021114s003lbl.pdf	Primary		Approved 8429	BETAXON Approved Use BETAXON™ (levobetaxolol hydrochloride ophthalmic suspension) 0.5% is indicated for lowering intraocular pressure in patients with chronic open-angle glaucoma or ocular hypertension. Launch Date 9.5126402E11
Ocular hypertension 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021114s003lbl.pdf	Primary		Approved 8429	BETAXON Approved Use BETAXON™ (levobetaxolol hydrochloride ophthalmic suspension) 0.5% is indicated for lowering intraocular pressure in patients with chronic open-angle glaucoma or ocular hypertension. Launch Date 9.5126402E11

C_max

Value	Dose	Co-administered	Analyte	Population
4.7 ng/g OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/021114_S000_BETAXON%200.5%25_PHARMR_P1.PDF	1 drop 2 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LEVOBETAXOLOL plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.5 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021114s003lbl.pdf	1 drop 2 times / day steady-state, ocular dose: 1 drop route of administration: Ocular experiment type: STEADY-STATE co-administered:		LEVOBETAXOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
10.4 ng × h/g OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/021114_S000_BETAXON%200.5%25_PHARMR_P1.PDF	1 drop 2 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LEVOBETAXOLOL plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.6 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/021114_S000_BETAXON%200.5%25_PHARMR_P1.PDF	1 drop 2 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LEVOBETAXOLOL plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
20 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021114s003lbl.pdf	1 drop 2 times / day steady-state, ocular dose: 1 drop route of administration: Ocular experiment type: STEADY-STATE co-administered:		LEVOBETAXOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
48% OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/021114_S000_BETAXON%200.5%25_PHARMR_P1.PDF	1 drop 2 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LEVOBETAXOLOL plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

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://pubmed.ncbi.nlm.nih.gov/18289898/	unhealthy, 1 - 6 years n = 48 Health Status: unhealthy Condition: pediatric glaucomas Age Group: 1 - 6 years Sex: M+F Population Size: 48 Sources: https://pubmed.ncbi.nlm.nih.gov/18289898/	Other AEs: Eye disorders NEC, Bradycardia... Other AEs: Eye disorders NEC (6 patients) Bradycardia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18289898/

AEs

AE	Significance	Dose	Population
Bradycardia	1 patient	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://pubmed.ncbi.nlm.nih.gov/18289898/	unhealthy, 1 - 6 years n = 48 Health Status: unhealthy Condition: pediatric glaucomas Age Group: 1 - 6 years Sex: M+F Population Size: 48 Sources: https://pubmed.ncbi.nlm.nih.gov/18289898/
Eye disorders NEC	6 patients	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://pubmed.ncbi.nlm.nih.gov/18289898/	unhealthy, 1 - 6 years n = 48 Health Status: unhealthy Condition: pediatric glaucomas Age Group: 1 - 6 years Sex: M+F Population Size: 48 Sources: https://pubmed.ncbi.nlm.nih.gov/18289898/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10514276/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P000CEM
1PlusChem LLC	1P00E9BN
1PlusChem LLC	1P00H9FD
A2B Chem	AG64467
A2B Chem	AI04569
ABI Chem	AC1L1TO2
ABI Chem	AC1Q58SH
AK Scientific	2266AH
AK Scientific	K696
AK Scientific	V1820
AK Scientific	W0012
AK Scientific, Inc. (AKSCI)	K696	http://www.aksci.com/item_detail.php?cat=K696
AbovChem LLC	HY-B0381
AbovChem LLC	HY-B0381A
AbovChem LLC	HY-B0381B
Achemo Scientific Limited	AC-74128	http://www.achemo.com/search/?Keyword= 93221-48-8
Adooq BioScience	A11721	https://www.adooq.com/betaxolol.html
Alinda	IVK/0069350
Ambeed	A140706
Angene	AGN-PC-07A1RI
Angene	AGN-PC-0JL43F
ApexBio Technology	B1352
ApexBio Technology	B1353
AstaTech	C71529
AstaTech	C75987
AstaTech	T71164
BLD Pharm	BD116615
BLD Pharm	BD116616
BLD Pharm	BD136218
BOC Sciences	116209-55-3
BOC Sciences	63659-18-7
BOC Sciences	63659-19-8
BOC Sciences	93221-48-8
BioSynth	Q-200714
BioSynth	Q-200715
BlocksMatrix Scientific	147887
Bosche Scientific	B6271
Cayman Chemical	18625
Chem Scene	CS-2452
Chem Scene	CS-2453
Chem Scene	CS-5154
ChemShuttle	113818
ChemShuttle	151583
ChemShuttle	151868
Chemieliva Pharmaceutical Co., Ltd	PBCM0996918
Clearsynth	CS-O-05769	http://www.clearsynth.com/en/CSO05769.html
Compound Cloud	107952
Compound Cloud	2369
Compound Cloud	60656
Compound Cloud	60657
Hairui	HR136954
Hairui	HR137052
Hangzhou APIChem Technology	AC-1115
Hangzhou APIChem Technology	AC-1412
Hangzhou APIChem Technology	AC-30590
Hangzhou Yuhao Chemical Technology	RT3647
Hangzhou Yuhao Chemical Technology	YH11405
Hangzhou Yuhao Chemical Technology	YH26322
HongKong Chemhere	SCD02343
IBScreen	BB_SC-12516
IBScreen	Bio-0117
KeyOrganics	AS-14125
KeyOrganics	AS-18082
KeyOrganics	AS-74909
Lab Network	LN01282429
Lab Network	LN01283286
Lab Network	LN01343836
Lab Network	LN03252478
Lab Seeker	SC-23071
Lab Seeker	SC-23389
Lan Pharmatech	LAN-B80147
MedChem Express	HY-B0381
MedChem Express	HY-B0381A
MedChem Express	HY-B0381B
MolPort	MolPort-003-666-823
MolPort	MolPort-003-845-027
MolPort	MolPort-005-977-072
MolPort	MolPort-019-999-775
MolPort	MolPort-027-720-680
Molnova	M15414
Molnova	M17850
Molnova	M18938
MuseChem	M138696
MuseChem	R006050
MuseChem	R058657
NovoSeek	60657
PBMR Labs	RBK_109886
PI Chemicals	PI-48019
Pharmeks	PHAR219265
Princeton BioMolecular Research	OSSM_121219
Ryan Scientific	Hydrocortisone_Valerate
Selleck Chemicals	S1827
Selleck Chemicals	S2091
Selleck Chemicals	S4085
ShangHai Biochempartner	BCP02967
ShangHai Biochempartner	BCP12964
Sigma Aldrich	1069903
Sigma Aldrich	1069903\|USP
Sigma Aldrich	B1103000\|SIAL
Sigma Aldrich	B5683
Sigma Aldrich	Y0001360\|SIAL
Smolecule	S532927	http://www.smolecule.com/products/s532927
StruChem	SC-23071
THE BioTek	bt-273325	https://www.thebiotek.com/product/inhibitors/bt-273325
TargetMol	T0226
TargetMol	T6408
TargetMol	T6565
Tetrahedron	TS65181
Tocris	906
Toronto Research Chemicals	B327980
Toronto Research Chemicals	B328000
Vitas-M Laboratory	STK636241
Wonderchem	WD06I2I
Wonderchem	WD06I2J
ZINC	ZINC000001530567	http://zinc15.docking.org/substances/ZINC000001530567
eMolecules	27677666
eMolecules	299964284
eMolecules	44696177
eMolecules	535239
eMolecules	901469
mcule	MCULE-1936600161
mcule	MCULE-2260668292
mcule	MCULE-3171998071
mcule	MCULE-4387517163
mcule	MCULE-4826935492

PubMed

Title	Date	PubMed
Levobetaxolol (Betaxon) and other beta-adrenergic antagonists: preclinical pharmacology, IOP-lowering activity and sites of action in human eyes.	2001 Aug	11572462
Levobetaxolol-induced Up-regulation of retinal bFGF and CNTF mRNAs and preservation of retinal function against a photic-induced retinopathy.	2002 Apr	12076088
Metipranolol attenuates lipid peroxidation in rat brain: a comparative study with other antiglaucoma drugs.	2003 Oct	12898280

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose is one drop of BETAXON™ (levobetaxolol hydrochloride ophthalmic suspension) 0.5% in the affected eye(s) twice daily. In some patients, the intraocular pressure lowering responses to BETAXONTM Ophthalmic Suspension may require a few weeks to stabilize.

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:36:35 UTC 2023` Edited by `admin` on `Fri Dec 15 15:36:35 UTC 2023`
Record UNII	8MR4W4O06J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEVOBETAXOLOL HYDROCHLORIDE

Official Name

English

(-)-(S)-1-(P-(2-(CYCLOPROPYLMETHOXY)ETHYL)PHENOXY)-3-(ISOPROPYLAMINO)-2-PROPANOL HYDROCHLORIDE

Common Name

English

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

Systematic Name

English

BETAXON

Brand Name

English

LEVOBETAXOLOL HYDROCHLORIDE [USAN]

Common Name

English

LEVOBETAXOLOL HYDROCHLORIDE [MART.]

Common Name

English

AL-1577A

Code

English

Levobetaxolol hydrochloride [WHO-DD]

Common Name

English

AL1577A

Code

English

LEVOBETAXOLOL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

LEVOBETAXOLOL HCL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29576