CARTEOLOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H24N2O3
Molecular Weight	292.3734
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)NCC(O)COC1=CC=CC2=C1CCC(=O)N2

InChI

InChIKey=LWAFSWPYPHEXKX-UHFFFAOYSA-N

InChI=1S/C16H24N2O3/c1-16(2,3)17-9-11(19)10-21-14-6-4-5-13-12(14)7-8-15(20)18-13/h4-6,11,17,19H,7-10H2,1-3H3,(H,18,20)

HIDE SMILES / InChI

Molecular Formula	C16H24N2O3
Molecular Weight	292.3734
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.drugs.com/pro/carteolol.html
Curator's Comment: description was created based on several sources, including: http://www.anvisa.gov.br/datavisa/fila_bula/frmVisualizarBula.asp?pNuTransacao=922652015&pIdAnexo=2432882 | http://www.rxlist.com/carteolol-hydrochloride-drug.htm | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5f82e53e-d6db-432f-af68-9de88d1b1720

Carteolol is a nonselective beta-adrenoceptor blocking agent for ophthalmic use. It has been shown to be effective in lowering intraocular pressure and may be used in patients with chronic open-angle glaucoma and intraocular hypertension. It may be used alone or in combination with other intraocular pressure lowering medications. The following adverse reactions have been reported: transient eye irritation, burning, tearing, conjunctival hyperemia and edema. Carteolol may cause bradycardia and decreased blood pressure, headache, arrhythmia, syncope, heart block, cerebral vascular accident, cerebral ischemia, congestive heart failure, palpitation, nausea, depression. Carteolol should be used with caution in patients who are receiving a beta-adrenergic blocking agent orally, because of the potential for additive effects on systemic beta-blockade.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adenylate Cyclase (guinea pig) 2 Target ID: Adenylate Cyclase (guinea pig) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16160085	Activator 1430	635.0 nM [EC50]
Beta-1 adrenergic receptor 158 Target ID: CHEMBL5471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16160085	Partial Agonist 290	9.37 null [pKi]
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15526107	Antagonist 2778
Cytochrome P450 2D1 2 Target ID: CHEMBL2475 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9413916	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic open-angle glaucoma 6 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5f82e53e-d6db-432f-af68-9de88d1b1720	Primary		Approved 8429	OCUPRESS Approved Use Carteolol hydrochloride ophthalmic solution USP, 1%, has been shown to be effective in lowering intraocular pressure and may be used in patients with chronic open-angle glaucoma and intraocular hypertension. It may be used alone or in combination with other intraocular pressure lowering medications. Launch Date 1990
Intraocular hypertension 2 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=571fe550-399d-4296-835c-37aa1ab9b409	Primary		Approved 8429	OCUPRESS Approved Use Carteolol hydrochloride ophthalmic solution USP, 1%, has been shown to be effective in lowering intraocular pressure and may be used in patients with chronic open-angle glaucoma and intraocular hypertension. It may be used alone or in combination with other intraocular pressure lowering medications. Launch Date 1990

C_max

Value	Dose	Analyte	Population
3.64 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16003515	2 % 2 times / day multiple, ocular dose: 2 % route of administration: Ocular experiment type: MULTIPLE co-administered:	CARTEOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.998 ng/mL REVIEW https://www.pmda.go.jp/files/000223317.pdf	1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered:	CARTEOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.627 ng/mL EXPERIMENT https://www.pmda.go.jp/files/000223317.pdf	1 drop 1 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:	CARTEOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
10.27 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16003515	2 % 2 times / day multiple, ocular dose: 2 % route of administration: Ocular experiment type: MULTIPLE co-administered:	CARTEOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12.7 ng × h/mL REVIEW https://www.pmda.go.jp/files/000223317.pdf	1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered:	CARTEOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
18 ng × h/mL EXPERIMENT https://www.pmda.go.jp/files/000223317.pdf	1 drop 1 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:	CARTEOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.5 h REVIEW https://www.pmda.go.jp/files/000223317.pdf	1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered:		CARTEOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
14.1 h EXPERIMENT https://www.pmda.go.jp/files/000223317.pdf	1 drop 1 times / day multiple, ocular dose: 1 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		CARTEOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
40% REVIEW https://www.ncbi.nlm.nih.gov/books/NBK501515/			CARTEOLOL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
60 mg 1 times / day single, oral Highest studied dose Dose: 60 mg, 1 times / day Route: oral Route: single Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1349493/	healthy, 23 n = 8 Health Status: healthy Age Group: 23 Sex: M+F Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/1349493/	Sources: https://pubmed.ncbi.nlm.nih.gov/1349493/
60 mg 1 times / day multiple, oral Highest studied dose Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6697637/	unhealthy, 55.6 n = 20 Health Status: unhealthy Condition: hypertension Age Group: 55.6 Sex: M Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/6697637/	Sources: https://pubmed.ncbi.nlm.nih.gov/6697637/
2 % 2 times / day multiple, ophthalmic Highest studied dose Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1554974/	unhealthy, adult n = 43 Health Status: unhealthy Condition: ocular hypertension & open angle glaucoma Age Group: adult Sex: M+F Population Size: 43 Sources: https://pubmed.ncbi.nlm.nih.gov/1554974/	Sources: https://pubmed.ncbi.nlm.nih.gov/1554974/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587	substrate 1037 inhibitor 1767	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478 CYP2E1 882	CYP2D1 7 CYP1A1 349 CYP1A2 1054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C19 991 CYP2E1 667 UGT 192

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	yes [Km 183 uM]
CYP2D1 7	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9413916/ Page: -	yes
UGT 192	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/4092726/ Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3437	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3437
ChemicalBook	CB0268673	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0268673
MolPort	MolPort-006-167-570	https://www.molport.com/shop/molecule-link/MolPort-006-167-570

PubMed

Title	Date	PubMed
[Combination of slow-release diltiazem and a beta-blocker in arterial hypertension. 2 cases of cardiogenic shock with severe bradycardia].	1990 Sep-Oct	1979694
Beta 2-adrenoceptor-mediated intrinsic sympathomimetic activity of carteolol: an in vivo study.	2004 Nov	15526107
Screening for library-assisted identification and fully validated quantification of 22 beta-blockers in blood plasma by liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization.	2004 Nov 26	15595665
Effects of glaucoma drugs on ocular hemodynamics in normal tension glaucoma: a randomized trial comparing bimatoprost and latanoprost with dorzolamide [ISRCTN18873428].	2005 Apr 5	15811188
In vitro evidence that carteolol is a nonconventional partial agonist of guinea pig cardiac beta1-adrenoceptors: a comparison with xamoterol.	2005 Dec	16160085
Comparison of carteolol plasmatic levels after repeated instillations of long-acting and regular formulations of carteolol 2% in glaucoma patients.	2005 Dec	16003515
Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro.	2005 Mar	15725891
Study of effects of antiglaucoma eye drops on N-methyl-D-aspartate-induced retinal damage.	2005 Nov-Dec	16365790
Ventricular tachycardia in a neonate with prenatally diagnosed cardiac tumors: a case with tuberous sclerosis.	2005 Sep-Oct	16132312
[A case of severe glaucoma with pseudopemphigoid successfully treated by filtration surgery using amniotic membrane].	2006 Apr	16642950
Additive effect of dorzolamide or carteolol to latanoprost in primary open-angle glaucoma: a prospective randomized crossover trial.	2006 Aug	16865013
Effects of antiglaucoma drugs on calcium mobility in cultured corneal endothelial cells.	2006 Feb	16568722
Comparison of the additive effects of nipradilol and carteolol to latanoprost in open-angle glaucoma.	2006 Jan-Feb	16453185
Environmentally responsive ophthalmic gel formulation of carteolol hydrochloride.	2006 Jan-Feb	16401594
The management of glaucoma and intraocular hypertension: current approaches and recent advances.	2006 Jun	18360593
Effects of antiglaucoma drugs on cellular proliferation in cultured human corneal keratocytes.	2006 Mar	16602276
Beta-blocker eye drops.	2006 May 30-Jun 5	16764382
Improvement of the ocular bioavailability of carteolol by ion pair.	2006 Oct	17076627
[The deleterious effect of certain surface active agents on the ocular surface].	2007	17718239
Ocular carteolol: a review of its use in the management of glaucoma and ocular hypertension.	2007	17571916
Separation of beta-receptor blockers and analogs by capillary liquid chromatography (CLC) and pressurized capillary electrochromatography (pCEC) using a vancomycin chiral stationary phase column.	2007 Aug	17867552
Measurement of inflammatory cytokines by multicytokine assay in tears of patients with glaucoma topically treated with chronic drugs.	2007 Jan	16943231
Levobetaxolol hydrochloride: a review of its pharmacology and use in the treatment of chronic open-angle glaucoma and ocular hypertension.	2007 Jun	19668496
[Ocular hypotensive effect of 1% carteolol long-acting eye drops--a double-masked, randomized phase III study in ocular hypertension or primary open-angle glaucoma patients comparing long-acting carteolol eye drops vs. current product].	2007 Jun	17601060
Effects of beta-adrenergic receptor antagonists on oxidative stress in purified rat retinal ganglion cells.	2007 Jun 11	17615544
Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells.	2007 Mar	17389174
Hypoxia-induced retinal ganglion cell death and the neuroprotective effects of beta-adrenergic antagonists.	2007 May 7	17368577
Daily cost of glaucoma medications in China.	2007 Oct-Nov	18091176
Effects of switching from topical beta-blockers to latanoprost on intraocular pressure in patients with normal-tension glaucoma.	2008 Apr	18341431
Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells.	2008 Aug	18954319
Carteolol, a non-conventional partial agonist of beta(1)-adrenoceptors, relaxes phenylephrine-constricted rat aorta through antagonism at alpha(1)-adrenoceptors.	2008 Aug 20	18571646
[Screening, quantification and confirmation of beta-blockers in urine using gas chromatography-mass spectrometry].	2008 Jul	18959242
Recent advances in pharmacotherapy of glaucoma.	2008 Oct	20040958
Field-amplified on-line sample stacking for simultaneous enantioseparation and determination of some beta-blockers using capillary electrophoresis.	2008 Sep	18803220
Effects of prostaglandin analog therapy on the ocular surface of glaucoma patients.	2009	19668581
Comparison of the ocular tolerability of a latanoprost cationic emulsion versus conventional formulations of prostaglandins: an in vivo toxicity assay.	2009 Aug 25	19710954
Comparison of the analysis of beta-blockers by different techniques.	2009 Dec 1	19879818
Pharmacological evaluation of ocular beta-adrenoceptors in rabbit by tissue segment binding method.	2009 Jan 30	19087880
[Retrospective analysis of clinical characteristics of toxic anterior segment syndrome].	2009 Mar	19575916
In situ forming polymeric drug delivery systems.	2009 May	20490289
[Cytotoxicity of antiglaucoma ophthalmic solutions for human corneal endothelial cells].	2009 May	19489448
Changes in optic nerve head blood flow induced by the combined therapy of latanoprost and beta blockers.	2009 Nov	19053956
Patient persistence with first-line antiglaucomatous monotherapy.	2010 Apr 26	20463793
Incidence, severity and factors related to drug-induced keratoepitheliopathy with glaucoma medications.	2010 Apr 26	20463785
[The influence of carteolol and pentoxyphylin on the visual field in glaucoma patients--case reports of selected patients].	2010 Feb	20521510
Designing dendrimers for ocular drug delivery.	2010 Jan	19889480
Effect of carteolol hydrochloride on 24-hour variation of intraocular pressure in normal-tension glaucoma.	2010 Mar	20401563
Simultaneous quantification of carteolol and dorzolamide in rabbit aqueous humor and ciliary body by liquid chromatography/atmospheric pressure chemical ionization mass spectrometry.	2010 Mar 15	20153987
Predictors of additional intraocular pressure reduction in patients changed to latanoprost/timolol fixed combination.	2010 Mar 26	20346127
Mechanism of carteolol-induced cytosolic Ca2+ mobilization in cultured vascular smooth muscle cells.	2010 Sep-Oct	20416399

Patents

Sample Use Guides

In Vivo Use Guide

The usual dose is one drop of 1% solution in the affected eye(s) twice a day.

Route of Administration: Topical

In Vitro Use Guide

Carteolol hydrochloride at 1 mmol/L attenuated the UVB-induced cell damage when added before, during, or after UVB irradiation (P<0.01). Carteolol hydrochloride at 1 mmol/L (P<0.05) significantly inhibited H2O2-induced cell damage and was able to scavenge O2 (EC50 value: 48 mmol/L).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:20:38 GMT 2023` Edited by `admin` on `Fri Dec 15 16:20:38 GMT 2023`
Record UNII	8NF31401XG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CARTEOLOL

Official Name

English

2(1H)-QUINOLINONE, 5-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)-3,4-DIHYDRO-

Systematic Name

English

Carteolol [WHO-DD]

Common Name

English

5-(3-(TERT-BUTYLAMINO)-2-HYDROXYPROPOXY)-3,4-DIHYDROCARBOSTYRIL

Common Name

English

CARTEOLOL [JAN]

Common Name

English

carteolol [INN]

Common Name

English

CARTEOLOL [VANDF]

Common Name

English

CARTEOLOL [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C07AA15