Identification
- Summary
Carteolol is a beta adrenergic antagonist used to treat arrhythmia, angina, hypertension, and glaucoma.
- Brand Names
- Ocupress
- Generic Name
- Carteolol
- DrugBank Accession Number
- DB00521
- Background
A beta-adrenergic antagonist used as an anti-arrhythmia agent, an anti-angina agent, an antihypertensive agent, and an antiglaucoma agent.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Carteolol (DB00521)
- Weight
- Average: 292.3734
Monoisotopic: 292.178692644 - Chemical Formula
- C16H24N2O3
- Synonyms
- Carteolol
- Cartéolol
- Carteololum
Pharmacology
- Indication
For the treatment of intraocular hypertension and chronic open-angle glaucoma
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Increased intraocular pressure •••••••••••• ••••••••• Treatment of Increased intraocular pressure •••••••••••• ••••••••• Used in combination to treat Increased intraocular pressure •••••••••••• ••••••••• Used in combination to treat Increased intraocular pressure •••••••••••• ••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ABeta-2 adrenergic receptor antagonistHumans ABeta-1 adrenergic receptor antagonistpartial agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The most common effects expected with overdosage of a beta-adrenergic blocking agent are bradycardia, bronchospasm, congestive heart failure and hypotension.
- Pathways
Pathway Category Carteolol Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol Acebutolol may increase the arrhythmogenic activities of Carteolol. Acetyldigitoxin Acetyldigitoxin may increase the arrhythmogenic activities of Carteolol. Adenosine Adenosine may increase the arrhythmogenic activities of Carteolol. Ajmaline Ajmaline may increase the arrhythmogenic activities of Carteolol. Aliskiren Carteolol may increase the hypotensive activities of Aliskiren. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Carteolol hydrochloride 4797W6I0T4 51781-21-6 FYBXRCFPOTXTJF-UHFFFAOYSA-N - International/Other Brands
- Endak (Rottapharm/Madaus)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ocupress Solution 10 mg/1mL Ophthalmic Novartis Ophthalmics 2006-09-19 Not applicable US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Carteolol Hydrochloride Solution / drops 10 mg/1mL Ophthalmic Mesource Pharmaceuticals 2000-01-20 2016-12-30 US Carteolol Hydrochloride Solution / drops 10 mg/1mL Ophthalmic Bausch & Lomb Incorporated 2000-01-20 2018-06-30 US Carteolol Hydrochloride Solution 10 mg/1mL Ophthalmic Sandoz Inc 2000-01-05 Not applicable US
Categories
- ATC Codes
- S01ED55 — Carteolol, combinations
- S01ED — Beta blocking agents
- S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- S01ED — Beta blocking agents
- S01E — ANTIGLAUCOMA PREPARATIONS AND MIOTICS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- Drug Categories
- Adrenergic Agents
- Adrenergic Antagonists
- Adrenergic beta-Antagonists
- Agents causing hyperkalemia
- Alcohols
- Amines
- Amino Alcohols
- Antiarrhythmic agents
- Antiglaucoma Preparations and Miotics
- Antihypertensive Agents
- Autonomic Agents
- Beta Blocking Agents, Non-Selective
- Bradycardia-Causing Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Hypotensive Agents
- Negative Inotrope
- Neurotransmitter Agents
- Ophthalmologicals
- Peripheral Nervous System Agents
- Phenoxypropanolamines
- Potential QTc-Prolonging Agents
- Propanolamines
- Propanols
- QTc Prolonging Agents
- Quinolines
- Quinolones
- Sensory Organs
- Sympatholytics
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Cyclic carboximidic acid / Dihydroquinoline / Ether
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- secondary alcohol, quinolone (CHEBI:3437)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 8NF31401XG
- CAS number
- 51781-06-7
- 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
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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014662
- KEGG Drug
- D07624
- KEGG Compound
- C06874
- PubChem Compound
- 2583
- PubChem Substance
- 46507513
- ChemSpider
- 2485
- BindingDB
- 50040065
- 2116
- ChEBI
- 3437
- ChEMBL
- CHEMBL839
- Therapeutic Targets Database
- DAP000065
- PharmGKB
- PA164768736
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Carteolol
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Glaucoma 1 3 Completed Treatment Glaucoma / Ocular Hypertension 1 1 Completed Not Available Glaucoma / Ocular Hypertension 1
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
Form Route Strength Liquid Ophthalmic 20 mg/1ml Solution / drops Ophthalmic Solution; suspension Ophthalmic 1 % Solution / drops Ophthalmic 10 mg/1mL Solution / drops Ophthalmic 1 % Solution / drops Ophthalmic 2 % Solution Ophthalmic 10 mg/1mL - Prices
Unit description Cost Unit Carteolol HCl 1% Solution 15ml Bottle 57.82USD bottle Carteolol HCl 1% Solution 10ml Bottle 38.55USD bottle Carteolol HCl 1% Solution 5ml Bottle 22.13USD bottle Carteolol hcl 1% eye drops 3.93USD ml Cartrol 2.5 mg tablet 1.37USD tablet Cartrol 5 mg tablet 1.37USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 1.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.421 mg/mL ALOGPS logP 1.05 ALOGPS logP 1.42 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 13.41 Chemaxon pKa (Strongest Basic) 9.76 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 70.59 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 83.14 m3·mol-1 Chemaxon Polarizability 32.79 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9157 Blood Brain Barrier - 0.5578 Caco-2 permeable - 0.6897 P-glycoprotein substrate Substrate 0.9025 P-glycoprotein inhibitor I Non-inhibitor 0.6539 P-glycoprotein inhibitor II Non-inhibitor 0.9197 Renal organic cation transporter Non-inhibitor 0.8058 CYP450 2C9 substrate Non-substrate 0.7911 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.59 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7633 Ames test Non AMES toxic 0.8024 Carcinogenicity Non-carcinogens 0.9099 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4801 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9902 hERG inhibition (predictor II) Non-inhibitor 0.5237
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-06z0-9740000000-0b5ab7905026b4d1b8e0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000f-1090000000-f92d0312f69cf4fae9b9 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0890000000-f46057117b0d78f50dc5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-4190000000-8cfa61533b30590612ce Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-3900000000-9b0c81d3976fe361fe0d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-3910000000-f498c17f291baa28356b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9400000000-e5afa448153b6742811a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 185.0606745 predictedDarkChem Lite v0.1.0 [M-H]- 164.0475 predictedDeepCCS 1.0 (2019) [M+H]+ 186.0080745 predictedDarkChem Lite v0.1.0 [M+H]+ 166.40549 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.0863745 predictedDarkChem Lite v0.1.0 [M+Na]+ 172.49864 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistPartial 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:44