CARTEOLOL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H24N2O3.ClH
Molecular Weight	328.834
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)(C)NCC(O)COC1=C2CCC(=O)NC2=CC=C1

InChI

InChIKey=FYBXRCFPOTXTJF-UHFFFAOYSA-N

InChI=1S/C16H24N2O3.ClH/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);1H

HIDE SMILES / InChI

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 1447	635.0 nM [EC50]
Beta-1 adrenergic receptor 163 Target ID: CHEMBL5471 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16160085	Partial Agonist 297	9.37 null [pKi]
Beta-2 adrenergic receptor 209 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15526107	Antagonist 2849
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 8583	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 8583	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 Health Status: healthy Age Group: 23 Sex: M+F 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 Health Status: unhealthy Age Group: 55.6 Sex: M 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 Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1554974/	Sources: https://pubmed.ncbi.nlm.nih.gov/1554974/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057 CYP2E1 1060	CYP2D1 7 CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP2E1 729 UGT 219

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9342584/ Page: -	yes [Km 183 uM]
CYP2D1 7	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9413916/ Page: -	yes
UGT 219	substrate 4014 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
Safety and efficacy of changing to the travoprost/timolol maleate fixed combination (DuoTrav) from prior mono- or adjunctive therapy.	2010-05-14	20505839
Patient persistence with first-line antiglaucomatous monotherapy.	2010-04-26	20463793
Incidence, severity and factors related to drug-induced keratoepitheliopathy with glaucoma medications.	2010-04-26	20463785
Predictors of additional intraocular pressure reduction in patients changed to latanoprost/timolol fixed combination.	2010-03-26	20346127
Simultaneous quantification of carteolol and dorzolamide in rabbit aqueous humor and ciliary body by liquid chromatography/atmospheric pressure chemical ionization mass spectrometry.	2010-03-15	20153987
Effect of carteolol hydrochloride on 24-hour variation of intraocular pressure in normal-tension glaucoma.	2010-03	20401563
[The influence of carteolol and pentoxyphylin on the visual field in glaucoma patients--case reports of selected patients].	2010-02	20521510
Designing dendrimers for ocular drug delivery.	2010-01	19889480
Comparison of the analysis of beta-blockers by different techniques.	2009-12-01	19879818
Changes in optic nerve head blood flow induced by the combined therapy of latanoprost and beta blockers.	2009-11	19053956
Mechanism of carteolol-induced cytosolic Ca2+ mobilization in cultured vascular smooth muscle cells.	2009-09-24	20416399
Comparison of the ocular tolerability of a latanoprost cationic emulsion versus conventional formulations of prostaglandins: an in vivo toxicity assay.	2009-08-25	19710954
Ryanodine receptor-mediated arrhythmias and sudden cardiac death.	2009-08	19345240
In situ forming polymeric drug delivery systems.	2009-05	20490289
[Cytotoxicity of antiglaucoma ophthalmic solutions for human corneal endothelial cells].	2009-05	19489448
[Retrospective analysis of clinical characteristics of toxic anterior segment syndrome].	2009-03	19575916
Pharmacological evaluation of ocular beta-adrenoceptors in rabbit by tissue segment binding method.	2009-01-30	19087880
Effects of prostaglandin analog therapy on the ocular surface of glaucoma patients.	2009	19668581
The trabecular bypass stent in a pseudophakic glaucoma patient: A 1-year follow-up.	2008-12	19668446
Dysfunctional regulation of ocular blood flow: A risk factor for glaucoma?	2008-12	19668439
Recent advances in pharmacotherapy of glaucoma.	2008-10	20040958
Field-amplified on-line sample stacking for simultaneous enantioseparation and determination of some beta-blockers using capillary electrophoresis.	2008-09	18803220
Carteolol, a non-conventional partial agonist of beta(1)-adrenoceptors, relaxes phenylephrine-constricted rat aorta through antagonism at alpha(1)-adrenoceptors.	2008-08-20	18571646
Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells.	2008-08	18954319
[Screening, quantification and confirmation of beta-blockers in urine using gas chromatography-mass spectrometry].	2008-07	18959242
Neurodegenerative diseases of the retina and potential for protection and recovery.	2008-06	19305795
Effects of switching from topical beta-blockers to latanoprost on intraocular pressure in patients with normal-tension glaucoma.	2008-04	18341431
Daily cost of glaucoma medications in China.	2007-12-20	18091176
Separation of beta-receptor blockers and analogs by capillary liquid chromatography (CLC) and pressurized capillary electrochromatography (pCEC) using a vancomycin chiral stationary phase column.	2007-08	17867552
Effects of beta-adrenergic receptor antagonists on oxidative stress in purified rat retinal ganglion cells.	2007-06-11	17615544
Levobetaxolol hydrochloride: a review of its pharmacology and use in the treatment of chronic open-angle glaucoma and ocular hypertension.	2007-06	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].	2007-06	17601060
Hypoxia-induced retinal ganglion cell death and the neuroprotective effects of beta-adrenergic antagonists.	2007-05-07	17368577
Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells.	2007-03	17389174
Measurement of inflammatory cytokines by multicytokine assay in tears of patients with glaucoma topically treated with chronic drugs.	2007-01	16943231
[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
Improvement of the ocular bioavailability of carteolol by ion pair.	2006-10	17076627
Additive effect of dorzolamide or carteolol to latanoprost in primary open-angle glaucoma: a prospective randomized crossover trial.	2006-08	16865013
Beta-blocker eye drops.	2006-06-13	16764382
The management of glaucoma and intraocular hypertension: current approaches and recent advances.	2006-06	18360593
[A case of severe glaucoma with pseudopemphigoid successfully treated by filtration surgery using amniotic membrane].	2006-04	16642950
Effects of antiglaucoma drugs on cellular proliferation in cultured human corneal keratocytes.	2006-03	16602276
Effects of antiglaucoma drugs on calcium mobility in cultured corneal endothelial cells.	2006-02	16568722
Environmentally responsive ophthalmic gel formulation of carteolol hydrochloride.	2006-01-13	16401594
In vitro evidence that carteolol is a nonconventional partial agonist of guinea pig cardiac beta1-adrenoceptors: a comparison with xamoterol.	2005-12	16160085
Ventricular tachycardia in a neonate with prenatally diagnosed cardiac tumors: a case with tuberous sclerosis.	2005-09-01	16132312
Comparison of the additive effects of nipradilol and carteolol to latanoprost in open-angle glaucoma.	2005-02-18	16453185
Study of effects of antiglaucoma eye drops on N-methyl-D-aspartate-induced retinal damage.	2004-09-04	16365790
[Combination of slow-release diltiazem and a beta-blocker in arterial hypertension. 2 cases of cardiogenic shock with severe bradycardia].	1990-09-01	1979694

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).

Name

Type

Language

CARTROL

Preferred Name

English

CARTEOLOL HYDROCHLORIDE

Official Name

English

CARTEOLOL HYDROCHLORIDE [USP-RS]

Common Name

English

ABBOTT-43326

Code

English

CARTEOLOL HYDROCHLORIDE [USAN]

Common Name

English

CARTEOLOL HCL

Common Name

English

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

Common Name

English

NSC-300906

Code

English

Carteolol hydrochloride [WHO-DD]

Common Name

English

OCUPRESS

Brand Name

English

CARTEOLOL HYDROCHLORIDE [VANDF]

Common Name

English

OPC-1085

Code

English

CARTEOLOL HYDROCHLORIDE [MART.]

Common Name

English

CARTEOLOL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

CARTEOLOL HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

CARTEOLOL HYDROCHLORIDE [JAN]

Common Name

English

CARTEOLOL HYDROCHLORIDE [USP IMPURITY]

Common Name

English

5-[3-(tert-Butylamino)-2-hydroxypropoxy]-3,4-dihydrocarbostyril monohydrochloride

Common Name

English

CARTEOLOL HYDROCHLORIDE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29576