Tariquidar

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Tariquidar
Accession Number
DB06240
Type
Small Molecule
Groups
Investigational
Description
Not Available
Structure
Thumb
Synonyms
Not Available
External IDs
XR-9576 / XR9576
Categories
UNII
J58862DTVD
CAS number
206873-63-4
Weight
Average: 646.744
Monoisotopic: 646.27913496
Chemical Formula
C38H38N4O6
InChI Key
LGGHDPFKSSRQNS-UHFFFAOYSA-N
InChI
InChI=1S/C38H38N4O6/c1-45-33-18-25-14-16-42(23-28(25)19-34(33)46-2)15-13-24-9-11-29(12-10-24)40-38(44)30-20-35(47-3)36(48-4)21-32(30)41-37(43)27-17-26-7-5-6-8-31(26)39-22-27/h5-12,17-22H,13-16,23H2,1-4H3,(H,40,44)(H,41,43)
IUPAC Name
N-[2-({4-[2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]phenyl}carbamoyl)-4,5-dimethoxyphenyl]quinoline-3-carboxamide
SMILES
COC1=CC2=C(CN(CCC3=CC=C(NC(=O)C4=CC(OC)=C(OC)C=C4NC(=O)C4=CN=C5C=CC=CC5=C4)C=C3)CC2)C=C1OC

Pharmacology

Indication

Investigated for use/treatment in ovarian cancer, lung cancer, and breast cancer.

Pharmacodynamics
Not Available
Mechanism of action

Tariquidar is an anthranilic acid derivative third generation P-glycoprotein (P-gp) inhibitors. P-gp is a transport protein found in normal cells that has many trasport and modulatory functions, from affecting the distribution and bioavailability of drugs to mediating the migration of dendritic cells. P-gp is responsible for multidrug resistance through transport of anti-cancer drugs out of their target cells. It is proposed that tariquidar's and its derivatives may bind to the H-binding site of P-gp through multiple mechanisms of binding.

TargetActionsOrganism
UMultidrug resistance protein 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Tariquidar.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Tariquidar.
Ascorbic acidThe serum concentration of Ascorbic acid can be increased when it is combined with Tariquidar.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Tariquidar.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Tariquidar.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Tariquidar.
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Tariquidar.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Tariquidar.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Tariquidar.
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Tariquidar.
Food Interactions
Not Available

References

General References
  1. Muller H, Pajeva IK, Globisch C, Wiese M: Functional assay and structure-activity relationships of new third-generation P-glycoprotein inhibitors. Bioorg Med Chem. 2008 Mar 1;16(5):2448-62. Epub 2007 Nov 28. [PubMed:18083034]
  2. Martin C, Berridge G, Mistry P, Higgins C, Charlton P, Callaghan R: The molecular interaction of the high affinity reversal agent XR9576 with P-glycoprotein. Br J Pharmacol. 1999 Sep;128(2):403-11. [PubMed:10510451]
External Links
ChemSpider
130650
BindingDB
50075373
ChEMBL
CHEMBL348475
Wikipedia
Tariquidar

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAdenaocortical Carcinoma / Coldrhood Cancer / Refractory Cancer / Sarcomas / Wilms' tumor1
1CompletedTreatmentCancer of the Ovary / Cancer, Breast / Cancers / Lung Cancers1
2CompletedDiagnosticCancers1
2CompletedTreatmentAdrenal Cortex Neoplasms1
2CompletedTreatmentCervix Neoplasms / Neoplasms, Lung / Neoplasms, Ovarian / Renal Neoplasms1
2CompletedTreatmentNeoplasms, Breast1
3TerminatedNot AvailableStage IIIb Non-small Cell Lung Cancer / Stage IV Non-Small Cell Lung Cancer2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00202 mg/mLALOGPS
logP5.26ALOGPS
logP5.68ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)11.45ChemAxon
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area111.25 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity188.12 m3·mol-1ChemAxon
Polarizability70.07 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Benzanilides
Alternative Parents
Quinoline-3-carboxamides / Dimethoxybenzenes / Tetrahydroisoquinolines / Benzamides / Methoxyanilines / Phenethylamines / Pyridinecarboxylic acids and derivatives / Anisoles / Benzoyl derivatives / Phenoxy compounds
show 11 more
Substituents
Benzanilide / Quinoline-3-carboxamide / Quinoline / Tetrahydroisoquinoline / Dimethoxybenzene / O-dimethoxybenzene / Pyridine carboxylic acid or derivatives / Benzamide / Benzoic acid or derivatives / Methoxyaniline
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da

Drug created on March 19, 2008 10:19 / Updated on August 02, 2018 05:35