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Details

Stereochemistry RACEMIC
Molecular Formula C20H33N3O3
Molecular Weight 363.4943
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TALINOLOL

SMILES

CC(C)(C)NCC(O)COC1=CC=C(NC(=O)NC2CCCCC2)C=C1

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 363.4943
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
The Cardiovascular Society in the GDR (German Democratic Republic).
2002
Apricot extract inhibits the P-gp-mediated efflux of talinolol.
2002 Dec
Increasing sample throughput in pharmacological studies by using dual-column liquid chromatography with tandem mass spectrometry.
2002 Mar 1
The effects of the human MDR1 genotype on the expression of duodenal P-glycoprotein and disposition of the probe drug talinolol.
2002 Nov
Inhibitory effect of fruit extracts on P-glycoprotein-related efflux carriers: an in-vitro screening.
2002 Sep
Efflux ratio cannot assess P-glycoprotein-mediated attenuation of absorptive transport: asymmetric effect of P-glycoprotein on absorptive and secretory transport across Caco-2 cell monolayers.
2003 Aug
pH-dependent bidirectional transport of weakly basic drugs across Caco-2 monolayers: implications for drug-drug interactions.
2003 Aug
Quantitation of talinolol and other beta-blockers by capillary electrophoresis for in vitro drug absorption studies.
2003 Aug
Comparison of talinolol and atenolol effects on blood pressure in relation to lipid and glucose metabolic parameters. Results from the TALIP study.
2003 Jan
Pulmonary absorption rate and bioavailability of drugs in vivo in rats: structure-absorption relationships and physicochemical profiling of inhaled drugs.
2003 Jun
Variability of intestinal expression of P-glycoprotein in healthy volunteers as described by absorption of talinolol from four bioequivalent tablets.
2003 Mar
Different dissolution media lead to different crystal structures of talinolol with impact on its dissolution and solubility.
2003 Sep
The MDR1 (ABCB1) gene polymorphism and its clinical implications.
2004
Effect of simulated intestinal fluid on drug permeability estimation across Caco-2 monolayers.
2004 Apr 15
Association between the number of coadministered P-glycoprotein inhibitors and serum digoxin levels in patients on therapeutic drug monitoring.
2004 Apr 2
HPLC with programmed wavelength fluorescence detection for the simultaneous determination of marker compounds of integrity and P-gp functionality in the Caco-2 intestinal absorption model.
2004 Mar 10
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
Comparative effects on intestinal absorption in situ by P-glycoprotein-modifying HIV protease inhibitors.
2004 Oct
Carbamazepine regulates intestinal P-glycoprotein and multidrug resistance protein MRP2 and influences disposition of talinolol in humans.
2004 Sep
[Suicidal fatal beta-blocker intoxication].
2004 Sep
P-glycoprotein and surfactants: effect on intestinal talinolol absorption.
2005 Jan
Selective downregulation of the MDR1 gene product in Caco-2 cells by stable transfection to prove its relevance in secretory drug transport.
2005 Jan-Feb
Determination of talinolol in human plasma using automated on-line solid phase extraction combined with atmospheric pressure chemical ionization tandem mass spectrometry.
2005 Jun 5
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.
2005 Oct 4
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
In silico modeling of non-linear drug absorption for the P-gp substrate talinolol and of consequences for the resulting pharmacodynamic effect.
2006 Aug
Roles of rifampicin in drug-drug interactions: underlying molecular mechanisms involving the nuclear pregnane X receptor.
2006 Feb 15
Bidirectional membrane transport: simulations of transport inhibition in uptake studies explain data obtained with flavonoids.
2006 Nov
[Interrelationship between changes of rate and variability of cardiac rhythm under influence of beta-adrenoblockers].
2007
Method development aspects for the quantitation of pharmaceutical compounds in human plasma with a matrix-assisted laser desorption/ionization source in the multiple reaction monitoring mode.
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
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
Comparison of drug transporter gene expression and functionality in Caco-2 cells from 10 different laboratories.
2008 Dec 18
Are decision trees a feasible knowledge representation to guide extraction of critical information from randomized controlled trial reports?
2008 Oct 28
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
Intestinal perfusion with mesenteric blood sampling in wild-type and knockout mice: evaluation of a novel tool in biopharmaceutical drug profiling.
2009 Jun
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 pomegranate juice pre-treatment on the transport of carbamazepine across rat intestine.
2010
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
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 Fri Dec 15 16:13:20 GMT 2023
Edited
by admin
on Fri Dec 15 16:13:20 GMT 2023
Record UNII
3S82268BKG
Record Status Validated (UNII)
Record Version
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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 Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
WHO-VATC QC07AB13
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
Code System Code Type Description
RXCUI
37546
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL152067
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
DRUG BANK
DB11770
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
EVMPD
SUB10804MIG
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
INN
3313
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
DRUG CENTRAL
2557
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
MERCK INDEX
m10440
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY Merck Index
FDA UNII
3S82268BKG
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID6046426
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
CAS
57460-41-0
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
PUBCHEM
68770
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
SMS_ID
100000083017
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
MESH
C011550
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
WIKIPEDIA
TALINOLOL
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
NCI_THESAURUS
C73020
Created by admin on Fri Dec 15 16:13:20 GMT 2023 , Edited by admin on Fri Dec 15 16:13:20 GMT 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY