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Details

Stereochemistry RACEMIC
Molecular Formula C20H33N3O3
Molecular Weight 363.4951
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TALINOLOL

SMILES

CC(C)(C)NCC(COc1ccc(cc1)NC(=NC2CCCCC2)O)O

InChI

InChIKey=MXFWWQICDIZSOA-UHFFFAOYSA-N
InChI=1S/C20H33N3O3/c1-20(2,3)21-13-17(24)14-26-18-11-9-16(10-12-18)23-19(25)22-15-7-5-4-6-8-15/h9-12,15,17,21,24H,4-8,13-14H2,1-3H3,(H2,22,23,25)

HIDE SMILES / InChI

Molecular Formula C20H33N3O3
Molecular Weight 363.4951
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 https://www.drugs.com/international/talinolol.html | https://www.ncbi.nlm.nih.gov/pubmed/8829891 | https://www.ncbi.nlm.nih.gov/pubmed/695

Talinolol (brand name Cordanurn) is the cardioselective beta-receptor antagonist which has been used for a long time in the treatment of various cardiovascular diseases and in tachyarrhythmia. The mean dosage is 10-20 mg intravenously administered over a period of 3-5 minutes, while the chronic oral dosage for this patient group amounts to 300mg/day. Cordanum eliminates the stimulating effect of catecholamines on the heart for physical and psychoemotional stress. The hypotensive effect is stabilized by the end of 2 weeks of course treatment. Reduces the frequency and severity of angina attacks; Contributes to the limitation of the heart attack zone and reduces the risk of arrhythmia in the presence of myocardial infarction, resulting in a decrease in mortality and the frequency of relapses. In average therapeutic doses, it has a less pronounced effect on the smooth muscles of the bronchi, myometrium, and peripheral arteries compared to non-selective beta-blockers. Talinolol is used in supraventricular (atrial fibrillation and flutter with high ventricular rate, paroxysmal supraventricular 1 tachycardia, sinus tachycardia) as well as ventricular extrasystoles and ventricular tachyarrhythmias. Patients with an increased tonus of the sympathetic nervous system related to sinus tachycardia, exercise-induced arrhythmias, hypertension, hyperthyroidism and coronary heart disease show a particularly positive reaction.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Cordanum

Approved Use

Unknown
Primary
Cordanum

Approved Use

Unknown
Primary
Cordanum

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Carbamazepine regulates intestinal P-glycoprotein and multidrug resistance protein MRP2 and influences disposition of talinolol in humans.
2004 Sep
Comparison of P-glycoprotein-mediated drug-digoxin interactions in Caco-2 with human and rodent intestine: relevance to in vivo prediction.
2005 Dec
P-glycoprotein and surfactants: effect on intestinal talinolol absorption.
2005 Jan
Modulation of drug transport by selected flavonoids: Involvement of P-gp and OCT?
2005 Jun
MDR1 genotype do not influence the absorption of a single oral dose of 100 mg talinolol in healthy Chinese males.
2005 Sep
Role of chemical structure in stereoselective recognition of beta-blockers and H1-antihistamines by human serum transferrin in capillary zone electrophoresis.
2006 Apr
Simvastatin does not influence the intestinal P-glycoprotein and MPR2, and the disposition of talinolol after chronic medication in healthy subjects genotyped for the ABCB1, ABCC2 and SLCO1B1 polymorphisms.
2006 Apr
A simple pharmacokinetics subroutine for modeling double peak phenomenon.
2006 Apr
Roles of rifampicin in drug-drug interactions: underlying molecular mechanisms involving the nuclear pregnane X receptor.
2006 Feb 15
[Interrelationship between changes of rate and variability of cardiac rhythm under influence of beta-adrenoblockers].
2007
Polymethoxylated flavones and other phenolic derivates from citrus in their inhibitory effects on P-glycoprotein-mediated transport of talinolol in Caco-2 cells.
2007 Apr 4
Unexpected effect of concomitantly administered curcumin on the pharmacokinetics of talinolol in healthy Chinese volunteers.
2007 Jul
Determination of talinolol in human plasma by high performance liquid chromatography-electrospray ionization mass spectrometry: application to pharmacokinetic study.
2007 Jun 15
Induction of intestinal P-glycoprotein by St John's wort reduces the oral bioavailability of talinolol.
2007 May
Grapefruit juice-drug interactions: Grapefruit juice and its components inhibit P-glycoprotein (ABCB1) mediated transport of talinolol in Caco-2 cells.
2007 Oct
Clinical drugs that interact with St. John's wort and implication in drug development.
2008
Influence of genetic polymorphisms on intestinal expression and rifampicin-type induction of ABCC2 and on bioavailability of talinolol.
2008 Apr
Role of the multidrug transporter proteins ABCB1 and ABCC2 in the diaplacental transport of talinolol in the term human placenta.
2008 Apr
Comparison of drug transporter gene expression and functionality in Caco-2 cells from 10 different laboratories.
2008 Dec 18
Effect of grapefruit juice, naringin, naringenin, and bergamottin on the intestinal carrier-mediated transport of talinolol in rats.
2008 Jun 25
Characterization of the epithelial permeation enhancing effect of basic butylated methacrylate copolymer--in vitro studies.
2008 May
Are decision trees a feasible knowledge representation to guide extraction of critical information from randomized controlled trial reports?
2008 Oct 28
Drug absorption modeling as a tool to define the strategy in clinical formulation development.
2008 Sep
Interactions between herbal medicines and prescribed drugs: an updated systematic review.
2009
IsoScore: automated localization of biotransformations by mass spectrometry using product ion scoring of virtual regioisomers.
2009 Jan
Assessing drug distribution in tissues expressing P-glycoprotein through physiologically based pharmacokinetic modeling: model structure and parameters determination.
2009 Jan 15
An improved primary human nasal cell culture for the simultaneous determination of transepithelial transport and ciliary beat frequency.
2009 Jul
Simulations of the nonlinear dose dependence for substrates of influx and efflux transporters in the human intestine.
2009 Jun
Intestinal perfusion with mesenteric blood sampling in wild-type and knockout mice: evaluation of a novel tool in biopharmaceutical drug profiling.
2009 Jun
Effect of Schisandra chinensis extract and Ginkgo biloba extract on the pharmacokinetics of talinolol in healthy volunteers.
2009 Mar
Concentration-dependent effect of naringin on intestinal absorption of beta(1)-adrenoceptor antagonist talinolol mediated by p-glycoprotein and organic anion transporting polypeptide (Oatp).
2009 Mar
Effects of Ginkgo biloba extract ingestion on the pharmacokinetics of talinolol in healthy Chinese volunteers.
2009 May
Cholesterol-mediated activation of P-glycoprotein: distinct effects on basal and drug-induced ATPase activities.
2009 May
Effect of bifendate on the pharmacokinetics of talinolol in healthy subjects.
2009 Nov
Antibody-dependent transplacental transfer of malaria blood-stage antigen using a human ex vivo placental perfusion model.
2009 Nov 24
The role of transporters in the pharmacokinetics of orally administered drugs.
2009 Sep
Effect of continuous silymarin administration on oral talinolol pharmacokinetics in healthy volunteers.
2009 Sep
Effect of pomegranate juice pre-treatment on the transport of carbamazepine across rat intestine.
2010
Evaluation of in vivo P-glycoprotein phenotyping probes: a need for validation.
2010 Apr
Validated HPLC method for quantitative determination of talinolol in rat plasma and application to a preclinical pharmacokinetic study.
2010 Jan
Species difference in the effect of grapefruit juice on intestinal absorption of talinolol between human and rat.
2010 Jan
Validation of a differential in situ perfusion method with mesenteric blood sampling in rats for intestinal drug interaction profiling.
2010 Jul
Overcoming multidrug resistance in human cancer cells by natural compounds.
2010 Jun
Pre-clinical evidence of enhanced oral bioavailability of the P-glycoprotein substrate talinolol in combination with morin.
2010 Mar
Quantitation of talinolol in rat plasma by LC-MS-MS.
2010 May-Jun
In vitro and in vivo evaluation of the effects of duloxetine on P-gp function.
2010 Nov
Fruit juice inhibition of uptake transport: a new type of food-drug interaction.
2010 Nov
Role of p-glycoprotein in region-specific gastrointestinal absorption of talinolol in rats.
2010 Sep
Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy.
2011 Jun
Patents

Patents

Sample Use Guides

In Vivo Use Guide
50 mg (1 table) 1-2 times a day or 100 mg (2 tablets) once a day.
Route of Administration: Other
In Vitro Use Guide
Caco-2 cells were used for activity evaluation. Transport experiments were performed at 37°C in Hanks’ Balanced Salt Solution (HBSS) containing 10 mM MES buffered to pH 6.5. Five milliliters of the prewarmed 0.25-5.0 mM rac-talinolol solution in buffered HBSS were added to either the apical (a) or the basolateral (b) side of the cell monolayer and drug-free buffered HBSS was added to the opposite side. Each chamber was bubbled with carbogen (95% O2, 5% CO2) for homogeneous mixing of each cell’s contents. The permeation experiment lasted for 2 hours. Samples (600 mkl) were taken every 20 minutes (for apical-to-basal transports from the basal side and vice versa) and were replaced with equal volumes of fresh buffered HBSS immediately. The samples were stored at — 20°C until analysis. Experiments with the P-gp inhibitor verapamil were performed at 500 jjlM verapamil concentrations on the apical and basolateral side; verapamil concentrations of 100 mkM have already been reported to reduce the efflux of drugs
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:44:46 UTC 2021
Edited
by admin
on Sat Jun 26 07:44:46 UTC 2021
Record UNII
3S82268BKG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TALINOLOL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
TALINOLOL [INN]
Common Name English
TALINOLOL [MART.]
Common Name English
TALINOLOL [MI]
Common Name English
TALINOLOL [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC C07AB13
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
WHO-VATC QC07AB13
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
Code System Code Type Description
RXCUI
37546
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL152067
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
DRUG BANK
DB11770
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
EVMPD
SUB10804MIG
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
INN
3313
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
DRUG CENTRAL
2557
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
MERCK INDEX
M10440
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY Merck Index
FDA UNII
3S82268BKG
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
EPA CompTox
57460-41-0
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
CAS
57460-41-0
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
PUBCHEM
68770
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
MESH
C011550
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
WIKIPEDIA
TALINOLOL
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
NCI_THESAURUS
C73020
Created by admin on Sat Jun 26 07:44:46 UTC 2021 , Edited by admin on Sat Jun 26 07:44:46 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY