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

Details

Stereochemistry RACEMIC
Molecular Formula C16H24N2O3
Molecular Weight 292.374
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARTEOLOL

SMILES

CC(C)(C)NCC(COc1cccc2c1CCC(=N2)O)O

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 292.374
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: 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

Curator's Comment:: Carteolol is distributed from the circulation to the brain with low penetrability. Known to be CNS penetrant in rat. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Adenylate Cyclase (guinea pig)
635.0 nM [EC50]
9.37 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

6.4342078E11
Primary
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

6.4342078E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.64 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
10.27 ng × h/mL
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12.5 h
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
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
40%
CARTEOLOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
healthy, 23
n = 8
Health Status: healthy
Age Group: 23
Sex: M+F
Population Size: 8
Sources:
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:
unhealthy, 55.6
n = 20
Health Status: unhealthy
Condition: hypertension
Age Group: 55.6
Sex: M
Population Size: 20
Sources:
2 % 2 times / day multiple, ophthalmic
Highest studied dose
Dose: 2 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 2 %, 2 times / day
Sources:
unhealthy, adult
n = 43
Health Status: unhealthy
Condition: ocular hypertension & open angle glaucoma
Age Group: adult
Sex: M+F
Population Size: 43
Sources:
OverviewDrug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
[Combination of slow-release diltiazem and a beta-blocker in arterial hypertension. 2 cases of cardiogenic shock with severe bradycardia].
1990 Sep-Oct
[Neuroprotection and vasoprotection in glaucoma].
2004
Characterization of intrinsic sympathomimetic activity of carteolol in rat cardiovascular preparations.
2004 May
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
Enantiomer separations on a vancomycin stationary phase and retention mechanism of pressurized capillary electrochromatography.
2004 Sep
Effects of glaucoma drugs on ocular hemodynamics in normal tension glaucoma: a randomized trial comparing bimatoprost and latanoprost with dorzolamide [ISRCTN18873428].
2005 Apr 5
Comparison of carteolol plasmatic levels after repeated instillations of long-acting and regular formulations of carteolol 2% in glaucoma patients.
2005 Dec
Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro.
2005 Mar
Study of effects of antiglaucoma eye drops on N-methyl-D-aspartate-induced retinal damage.
2005 Nov-Dec
Effects of antiglaucoma drugs on calcium mobility in cultured corneal endothelial cells.
2006 Feb
Comparison of the additive effects of nipradilol and carteolol to latanoprost in open-angle glaucoma.
2006 Jan-Feb
Environmentally responsive ophthalmic gel formulation of carteolol hydrochloride.
2006 Jan-Feb
The management of glaucoma and intraocular hypertension: current approaches and recent advances.
2006 Jun
Effects of antiglaucoma drugs on cellular proliferation in cultured human corneal keratocytes.
2006 Mar
Beta-blocker eye drops.
2006 May 30-Jun 5
[The deleterious effect of certain surface active agents on the ocular surface].
2007
Ocular carteolol: a review of its use in the management of glaucoma and ocular hypertension.
2007
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
Levobetaxolol hydrochloride: a review of its pharmacology and use in the treatment of chronic open-angle glaucoma and ocular hypertension.
2007 Jun
[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
Effects of beta-adrenergic receptor antagonists on oxidative stress in purified rat retinal ganglion cells.
2007 Jun 11
Cellular cytotoxicity of antiglaucoma drugs in cultured corneal endothelial cells.
2007 Mar
Daily cost of glaucoma medications in China.
2007 Oct-Nov
Effects of switching from topical beta-blockers to latanoprost on intraocular pressure in patients with normal-tension glaucoma.
2008 Apr
Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells.
2008 Aug
Carteolol, a non-conventional partial agonist of beta(1)-adrenoceptors, relaxes phenylephrine-constricted rat aorta through antagonism at alpha(1)-adrenoceptors.
2008 Aug 20
The trabecular bypass stent in a pseudophakic glaucoma patient: A 1-year follow-up.
2008 Dec
Dysfunctional regulation of ocular blood flow: A risk factor for glaucoma?
2008 Dec
[Screening, quantification and confirmation of beta-blockers in urine using gas chromatography-mass spectrometry].
2008 Jul
Neurodegenerative diseases of the retina and potential for protection and recovery.
2008 Jun
Recent advances in pharmacotherapy of glaucoma.
2008 Oct
Field-amplified on-line sample stacking for simultaneous enantioseparation and determination of some beta-blockers using capillary electrophoresis.
2008 Sep
Effects of prostaglandin analog therapy on the ocular surface of glaucoma patients.
2009
Ryanodine receptor-mediated arrhythmias and sudden cardiac death.
2009 Aug
Comparison of the ocular tolerability of a latanoprost cationic emulsion versus conventional formulations of prostaglandins: an in vivo toxicity assay.
2009 Aug 25
Comparison of the analysis of beta-blockers by different techniques.
2009 Dec 1
Pharmacological evaluation of ocular beta-adrenoceptors in rabbit by tissue segment binding method.
2009 Jan 30
[Retrospective analysis of clinical characteristics of toxic anterior segment syndrome].
2009 Mar
In situ forming polymeric drug delivery systems.
2009 May
[Cytotoxicity of antiglaucoma ophthalmic solutions for human corneal endothelial cells].
2009 May
Changes in optic nerve head blood flow induced by the combined therapy of latanoprost and beta blockers.
2009 Nov
Patient persistence with first-line antiglaucomatous monotherapy.
2010 Apr 26
Incidence, severity and factors related to drug-induced keratoepitheliopathy with glaucoma medications.
2010 Apr 26
[The influence of carteolol and pentoxyphylin on the visual field in glaucoma patients--case reports of selected patients].
2010 Feb
Designing dendrimers for ocular drug delivery.
2010 Jan
Effect of carteolol hydrochloride on 24-hour variation of intraocular pressure in normal-tension glaucoma.
2010 Mar
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
Predictors of additional intraocular pressure reduction in patients changed to latanoprost/timolol fixed combination.
2010 Mar 26
Safety and efficacy of changing to the travoprost/timolol maleate fixed combination (DuoTrav) from prior mono- or adjunctive therapy.
2010 May 14
Mechanism of carteolol-induced cytosolic Ca2+ mobilization in cultured vascular smooth muscle cells.
2010 Sep-Oct
Patents

Sample Use Guides

The usual dose is one drop of 1% solution in the affected eye(s) twice a day.
Route of Administration: Topical
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 Sat Jun 26 08:32:45 UTC 2021
Edited
by admin
on Sat Jun 26 08:32:45 UTC 2021
Record UNII
8NF31401XG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARTEOLOL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
2(1H)-QUINOLINONE, 5-(3-((1,1-DIMETHYLETHYL)AMINO)-2-HYDROXYPROPOXY)-3,4-DIHYDRO-
Systematic 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
CARTEOLOL [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC C07AA15
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
WHO-VATC QS01ED55
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
WHO-VATC QC07AA15
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
NDF-RT N0000000161
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
WHO-ATC S01ED05
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
WHO-ATC S01ED55
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
WHO-VATC QS01ED05
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
NDF-RT N0000175556
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
Code System Code Type Description
LACTMED
Carteolol
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
FDA UNII
8NF31401XG
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
EPA CompTox
51781-06-7
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
IUPHAR
7142
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
NCI_THESAURUS
C65291
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
CAS
51781-06-7
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL839
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
PUBCHEM
2583
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
INN
3990
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
DRUG BANK
DB00521
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
MERCK INDEX
M3136
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY Merck Index
EVMPD
SUB06150MIG
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
RXCUI
2116
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
CARTEOLOL
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
DRUG CENTRAL
520
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
MESH
D002354
Created by admin on Sat Jun 26 08:32:45 UTC 2021 , Edited by admin on Sat Jun 26 08:32:45 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC