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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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Carteolol HCl
  • Carteolol Hydrochloride
  • Carteololum [INN-Latin]
Brand names
  • Cartrol
  • Endak Hydrochloride
  • Ocupress
Brand name mixtures Not Available
Categories
  • Antihypertensive Agents
  • Adrenergic beta-Antagonists
  • Sympatholytics
  • Anti-Arrhythmia Agents
CAS number 51781-06-7
Weight Average: 292.3734
Monoisotopic: 292.178692644
Chemical Formula C16H24N2O3
InChI Key InChIKey=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)
Plain Text
IUPAC Name
5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinolin-2-one
SMILES
CC(C)(C)NCC(O)COC1=C2CCC(=O)NC2=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Quinolinones
  • Phenylpropylamines
  • (Iso)quinolines and Derivatives
  • Lactams
Substructures
  • Hydroxy Compounds
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Amino Ketones
  • Ethers
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Amino Alcohols
  • Heterocyclic compounds
  • Aromatic compounds
  • Quinolinones
  • Anisoles
  • Carboxamides and Derivatives
  • Phenylpropylamines
  • (Iso)quinolines and Derivatives
  • Lactams
  • Alcohols and Polyols
  • Phenyl Esters
  • Anilines
Pharmacology
Indication For the treatment of intraocular hypertension and chronic open-angle glaucoma
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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic.

Enzyme Metabolite Reaction Km Vmax
Cytochrome P450 2D6 8-Hydroxycarteolol 8-hydroxylation 183 467.52
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 Not Available
Pharmacoeconomics
Manufacturers
  • Alcon laboratories inc
  • Bausch and lomb inc
  • Novex pharma
  • Novartis pharmaceuticals corp
  • Abbott laboratories
Packagers
Dosage forms
Form Route Strength
Solution Ophthalmic
Prices
Unit description Cost Unit
Carteolol HCl 1% Solution 15ml Bottle 57.82 USD bottle
Carteolol HCl 1% Solution 10ml Bottle 38.55 USD bottle
Carteolol HCl 1% Solution 5ml Bottle 22.13 USD bottle
Carteolol hcl 1% eye drops 3.93 USD ml
Cartrol 2.5 mg tablet 1.37 USD tablet
Cartrol 5 mg tablet 1.37 USD tablet
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 1.1 PhysProp
Predicted Properties
Property Value Source
water solubility 4.21e-01 g/l ALOGPS
logP 1.05 ALOGPS
logP 1.42 ChemAxon Molconvert
logS -2.84 ALOGPS
pKa 14.19 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 70.59 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 83.14 ChemAxon Molconvert
polarizability 32.79 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  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
  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
  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
External Links
Resource Link
KEGG Compound C06874 Link_out
PubChem Compound 2583 Link_out
PubChem Substance 46507513 Link_out
ChemSpider 2485 Link_out
ChEBI 3437 Link_out
ChEMBL 3437 Link_out
Therapeutic Targets Database DAP000065 Link_out
PharmGKB PA448815 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic2/carteol.htm Link_out
Drugs.com http://www.drugs.com/cdi/carteolol-drops.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Carteolol Link_out
ATC Codes
  • C07AA15
  • S01ED05
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: antagonist

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 30-fold greater affinity than it does norepinephrine

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-1 adrenergic receptor

Pharmacological action: yes
Actions: partial agonist

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 equal affinity

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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
  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
  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
Enzymes

1. Cytochrome P450 2D6

Actions: substrate, inhibitor

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 antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2009 Nov 24. Pubmed
  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
Comments
Drug created on June 13, 2005 07:24 / Updated on October 28, 2011 16:19

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.