Identification

Name
Carteolol
Accession Number
DB00521  (APRD00195)
Type
Small Molecule
Groups
Approved
Description

A beta-adrenergic antagonist used as an anti-arrhythmia agent, an anti-angina agent, an antihypertensive agent, and an antiglaucoma agent. [PubChem]

Structure
Thumb
Synonyms
  • Carteolol
  • Carteololum
Product Ingredients
IngredientUNIICASInChI Key
Carteolol Hydrochloride4797W6I0T451781-21-6FYBXRCFPOTXTJF-UHFFFAOYSA-N
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carteolol HydrochlorideSolution10 mg/1mLOphthalmicSandoz2000-01-05Not applicableUs
Carteolol HydrochlorideSolution / drops10 mg/1mLOphthalmicBauch & Lomb Incorporated2000-01-20Not applicableUs
Carteolol HydrochlorideSolution / drops10 mg/1mLOphthalmicMesource Pharmaceuticals2000-01-202016-12-30Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
OcupressCarteolol Hydrochloride (10 mg/1mL)SolutionOphthalmicNovartis Ophthalmics2006-09-19Not applicableUs
International/Other Brands
Cartrol / Endak (Rottapharm/Madaus) / Ocupress (Novartis)
Categories
UNII
8NF31401XG
CAS number
51781-06-7
Weight
Average: 292.3734
Monoisotopic: 292.178692644
Chemical Formula
C16H24N2O3
InChI Key
LWAFSWPYPHEXKX-UHFFFAOYSA-N
InChI
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)
IUPAC Name
5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinolin-2-one
SMILES
CC(C)(C)NCC(O)COC1=CC=CC2=C1CCC(=O)N2

Pharmacology

Indication

For the treatment of intraocular hypertension and chronic open-angle glaucoma

Associated Conditions
Pharmacodynamics

Carteolol is a beta1 and beta2 (non-selective) adrenergic receptor-blocking agent that does not have significant intrinsic sympathomimetic, direct myocardial depressant, or local anesthetic (membrane-stabilizing) activity. Carteolol, when applied topically to the eye, has the action of reducing elevated, as well as normal, intraocular pressure, whether or not accompanied by glaucoma. Elevated intraocular pressure is a major risk factor in the pathogenesis of glaucomatous visual field loss and optic nerve damage. Carteolol reduces intraocular pressure with little or no effect on pupil size or accommodation in contrast to the miosis which cholinergic agents are known to produce.

Mechanism of action

The primary mechanism of the ocular hypotensive action of carteolol in reducing intraocular pressure is most likely a decrease in aqueous humor production. This process is initiated by the non-selective beta1 and beta2 adrenergic receptor blockade.

TargetActionsOrganism
ABeta-2 adrenergic receptor
antagonist
Human
ABeta-1 adrenergic receptor
partial agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

The most common effects expected with overdosage of a beta-adrenergic blocking agent are bradycardia, bronchospasm, congestive heart failure and hypotension.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Carteolol Action PathwayDrug action
Carteolol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limonene(4R)-limonene may decrease the antihypertensive activities of Carteolol.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Carteolol.
4-Methoxyamphetamine4-Methoxyamphetamine may increase the atrioventricular blocking (AV block) activities of Carteolol.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Carteolol.
AbediterolCarteolol may decrease the bronchodilatory activities of Abediterol.
AbirateroneThe serum concentration of Carteolol can be increased when it is combined with Abiraterone.
AcebutololAcebutolol may increase the hypotensive activities of Carteolol.
AceclofenacAceclofenac may decrease the antihypertensive activities of Carteolol.
AcemetacinThe therapeutic efficacy of Carteolol can be decreased when used in combination with Acemetacin.
AcepromazineCarteolol may increase the orthostatic hypotensive activities of Acepromazine.
Food Interactions
Not Available

References

Synthesis Reference

Tamura,Y., Nakagawa,K., Yoshizaki,S.and Murakami,N.; U.S.Patent 3,910,924; October 7, 1975; assigned to Otsuka Pharmaceutical Co., Ltd.

General References
  1. El-Kamel A, Al-Dosari H, Al-Jenoobi F: Environmentally responsive ophthalmic gel formulation of carteolol hydrochloride. Drug Deliv. 2006 Jan-Feb;13(1):55-9. [PubMed:16401594]
  2. Kuwahara K, Oizumi N, Fujisawa S, Tanito M, Ohira A: Carteolol hydrochloride protects human corneal epithelial cells from UVB-induced damage in vitro. Cornea. 2005 Mar;24(2):213-20. [PubMed:15725891]
  3. Trinquand C, Romanet JP, Nordmann JP, Allaire C: [Efficacy and safety of long-acting carteolol 1% once daily. A double-masked, randomized study]. J Fr Ophtalmol. 2003 Feb;26(2):131-6. [PubMed:12660585]
External Links
Human Metabolome Database
HMDB0014662
KEGG Compound
C06874
PubChem Compound
2583
PubChem Substance
46507513
ChemSpider
2485
BindingDB
50040065
ChEBI
3437
ChEMBL
CHEMBL839
Therapeutic Targets Database
DAP000065
PharmGKB
PA164768736
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Carteolol
ATC Codes
S01ED05 — CarteololS01ED55 — Carteolol, combinationsC07AA15 — Carteolol

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Alcon laboratories inc
  • Bausch and lomb inc
  • Novex pharma
  • Novartis pharmaceuticals corp
  • Abbott laboratories
Packagers
  • Alcon Laboratories
  • Apotex Inc.
  • Bausch & Lomb Inc.
  • Ciba Vision Canada Inc.
  • Falcon Pharmaceuticals Ltd.
  • Novartis AG
  • Novex Pharma
  • Otsuka America
  • Pharmaceutical Utilization Management Program VA Inc.
Dosage forms
FormRouteStrength
Solution / dropsOphthalmic10 mg/1mL
SolutionOphthalmic10 mg/1mL
Prices
Unit descriptionCostUnit
Carteolol HCl 1% Solution 15ml Bottle57.82USD bottle
Carteolol HCl 1% Solution 10ml Bottle38.55USD bottle
Carteolol HCl 1% Solution 5ml Bottle22.13USD bottle
Carteolol hcl 1% eye drops3.93USD ml
Cartrol 2.5 mg tablet1.37USD tablet
Cartrol 5 mg tablet1.37USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP1.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.421 mg/mLALOGPS
logP1.05ALOGPS
logP1.42ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.41ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area70.59 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.14 m3·mol-1ChemAxon
Polarizability32.79 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9157
Blood Brain Barrier-0.5578
Caco-2 permeable-0.6897
P-glycoprotein substrateSubstrate0.9025
P-glycoprotein inhibitor INon-inhibitor0.6539
P-glycoprotein inhibitor IINon-inhibitor0.9197
Renal organic cation transporterNon-inhibitor0.8058
CYP450 2C9 substrateNon-substrate0.7911
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.59
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7633
Ames testNon AMES toxic0.8024
CarcinogenicityNon-carcinogens0.9099
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4801 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9902
hERG inhibition (predictor II)Non-inhibitor0.5237
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroquinolines. These are derivatives of quinoline in which in which at least one double bond in the quinoline moiety are reduced by adding two hydrogen atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Hydroquinolines
Direct Parent
Hydroquinolines
Alternative Parents
Alkyl aryl ethers / Benzenoids / Cyclic carboximidic acids / Secondary alcohols / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Dihydroquinoline / Alkyl aryl ether / Benzenoid / Cyclic carboximidic acid / 1,2-aminoalcohol / Secondary alcohol / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Secondary amine / Ether
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
secondary alcohol, quinolone (CHEBI:3437)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Wheeldon NM, McDevitt DG, Lipworth BJ: Evaluation of in vivo partial beta 1/beta 2-agonist activity: a dose-ranging study with carteolol. Br J Clin Pharmacol. 1992 Apr;33(4):411-6. [PubMed:1349493]
  2. Bruck H, Poller U, Lussenhop H, Ponicke K, Temme T, Heusch G, Philipp T, Brodde OE: Beta 2-adrenoceptor-mediated intrinsic sympathomimetic activity of carteolol: an in vivo study. Naunyn Schmiedebergs Arch Pharmacol. 2004 Nov;370(5):361-8. Epub 2004 Oct 23. [PubMed:15526107]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Partial agonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Bruck H, Poller U, Lussenhop H, Ponicke K, Temme T, Heusch G, Philipp T, Brodde OE: Beta 2-adrenoceptor-mediated intrinsic sympathomimetic activity of carteolol: an in vivo study. Naunyn Schmiedebergs Arch Pharmacol. 2004 Nov;370(5):361-8. Epub 2004 Oct 23. [PubMed:15526107]
  3. Chidlow G, Melena J, Osborne NN: Betaxolol, a beta(1)-adrenoceptor antagonist, reduces Na(+) influx into cortical synaptosomes by direct interaction with Na(+) channels: comparison with other beta-adrenoceptor antagonists. Br J Pharmacol. 2000 Jun;130(4):759-66. [PubMed:10864881]
  4. Floreani M, Froldi G, Quintieri L, Varani K, Borea PA, Dorigo MT, Dorigo P: In vitro evidence that carteolol is a nonconventional partial agonist of guinea pig cardiac beta1-adrenoceptors: a comparison with xamoterol. J Pharmacol Exp Ther. 2005 Dec;315(3):1386-95. Epub 2005 Sep 13. [PubMed:16160085]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Kudo S, Uchida M, Odomi M: Metabolism of carteolol by cDNA-expressed human cytochrome P450. Eur J Clin Pharmacol. 1997;52(6):479-85. [PubMed:9342584]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 07:40