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Identification
NameCarteolol
Accession NumberDB00521  (APRD00195)
TypeSmall Molecule
GroupsApproved
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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Carteolol Hydrochloridesolution/ drops10 mg/mLophthalmicBausch & Lomb Incorporated2000-01-20Not applicableUs
Carteolol Hydrochloridesolution10 mg/mLophthalmicSandoz Inc.2000-01-05Not applicableUs
Carteolol Hydrochloridesolution/ drops10 mg/mLophthalmicMedsource Pharmaceuticals2000-01-20Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CartrolNot Available
EndakRottapharm/Madaus
OcupressNovartis
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Carteolol Hydrochloride
51781-21-6
Thumb
  • InChI Key: FYBXRCFPOTXTJF-UHFFFAOYNA-N
  • Monoisotopic Mass: 328.155370383
  • Average Mass: 328.834
DBSALT000319
Categories
UNII8NF31401XG
CAS number51781-06-7
WeightAverage: 292.3734
Monoisotopic: 292.178692644
Chemical FormulaC16H24N2O3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroquinolones. These are compounds containing a hydrogenated quinoline bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassQuinolones and derivatives
Direct ParentHydroquinolones
Alternative Parents
Substituents
  • Tetrahydroquinolone
  • Tetrahydroquinoline
  • Alkyl aryl ether
  • Benzenoid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Lactam
  • Carboxamide group
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of intraocular hypertension and chronic open-angle glaucoma
PharmacodynamicsCarteolol 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 actionThe 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

SubstrateEnzymesProduct
Carteolol
8-HydroxycarteololDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityThe 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
PathwayCategorySMPDB ID
Carteolol Action PathwayDrug actionSMP00658
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Alcon laboratories inc
  • Bausch and lomb inc
  • Novex pharma
  • Novartis pharmaceuticals corp
  • Abbott laboratories
Packagers
Dosage forms
FormRouteStrength
Solutionophthalmic10 mg/mL
Solution/ dropsophthalmic10 mg/mL
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.
PatentsNot Available
Properties
StateSolid
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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
ATC CodesS01ED05S01ED55C07AA15
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcepromazineAcepromazine may increase the hypotensive activities of Carteolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Carteolol is combined with Acetylcholine.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Carteolol.
AlfuzosinCarteolol may increase the orthostatic hypotensive activities of Alfuzosin.
AmiodaroneAmiodarone may increase the bradycardic activities of Carteolol.
BretyliumBretylium may increase the bradycardic activities of Carteolol.
BupivacaineThe serum concentration of Bupivacaine can be increased when it is combined with Carteolol.
ButabarbitalThe serum concentration of Carteolol can be decreased when it is combined with Butabarbital.
ButethalThe serum concentration of Carteolol can be decreased when it is combined with Butethal.
CabergolineCarteolol may increase the vasoconstricting activities of Cabergoline.
CarbacholThe risk or severity of adverse effects can be increased when Carteolol is combined with Carbachol.
CeritinibCarteolol may increase the bradycardic activities of Ceritinib.
ChlorpropamideCarteolol may increase the hypoglycemic activities of Chlorpropamide.
DigoxinCarteolol may increase the bradycardic activities of Digoxin.
DipivefrinDipivefrin may increase the atrioventricular blocking (AV block) activities of Carteolol.
DipyridamoleDipyridamole may increase the bradycardic activities of Carteolol.
DisopyramideDisopyramide may increase the bradycardic activities of Carteolol.
DronedaroneDronedarone may increase the bradycardic activities of Carteolol.
DuloxetineCarteolol may increase the orthostatic hypotensive activities of Duloxetine.
EsmololEsmolol may increase the bradycardic activities of Carteolol.
FingolimodCarteolol may increase the bradycardic activities of Fingolimod.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Carteolol.
HeptabarbitalThe serum concentration of Carteolol can be decreased when it is combined with Heptabarbital.
HexobarbitalThe serum concentration of Carteolol can be decreased when it is combined with Hexobarbital.
InfliximabInfliximab may decrease the antihypertensive activities of Carteolol.
IvabradineCarteolol may increase the bradycardic activities of Ivabradine.
LacosamideCarteolol may increase the atrioventricular blocking (AV block) activities of Lacosamide.
LevodopaCarteolol may increase the orthostatic hypotensive activities of Levodopa.
LidocaineThe serum concentration of Lidocaine can be increased when it is combined with Carteolol.
MepivacaineThe serum concentration of Mepivacaine can be increased when it is combined with Carteolol.
MethacholineThe risk or severity of adverse effects can be increased when Carteolol is combined with Methacholine.
MethohexitalThe serum concentration of Carteolol can be decreased when it is combined with Methohexital.
MidodrineCarteolol may increase the bradycardic activities of Midodrine.
NicorandilNicorandil may increase the hypotensive activities of Carteolol.
NifedipineNifedipine may increase the hypotensive activities of Carteolol.
OctreotideOctreotide may increase the bradycardic activities of Carteolol.
OrciprenalineCarteolol may decrease the activities of Orciprenaline.
PentobarbitalThe serum concentration of Carteolol can be decreased when it is combined with Pentobarbital.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Carteolol.
PrazosinCarteolol may increase the orthostatic hypotensive activities of Prazosin.
PrimidoneThe serum concentration of Carteolol can be decreased when it is combined with Primidone.
RegorafenibRegorafenib may increase the bradycardic activities of Carteolol.
ReserpineReserpine may increase the hypotensive activities of Carteolol.
RisperidoneCarteolol may increase the hypotensive activities of Risperidone.
RivastigmineRivastigmine may increase the bradycardic activities of Carteolol.
RuxolitinibRuxolitinib may increase the bradycardic activities of Carteolol.
SecobarbitalThe serum concentration of Carteolol can be decreased when it is combined with Secobarbital.
SufentanilSufentanil may increase the bradycardic activities of Carteolol.
TacrineTacrine may increase the bradycardic activities of Carteolol.
TheophyllineCarteolol may decrease the activities of Theophylline.
TofacitinibTofacitinib may increase the bradycardic activities of Carteolol.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Carteolol.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Carteolol.
Food InteractionsNot Available

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 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
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
substrateinhibitor
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23