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

Identification

Generic Name
Tariquidar
DrugBank Accession Number
DB06240
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 646.744
Monoisotopic: 646.27913496
Chemical Formula
C38H38N4O6
Synonyms
  • Tariquidar
External IDs
  • XR-9576
  • XR9576

Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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
UP-glycoprotein 1Not AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Tariquidar.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Tariquidar.
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Tariquidar.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Tariquidar.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Tariquidar.
AvatrombopagThe serum concentration of Avatrombopag can be increased when it is combined with Tariquidar.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Tariquidar.
Belantamab mafodotinThe serum concentration of Belantamab mafodotin can be increased when it is combined with Tariquidar.
BelinostatThe serum concentration of Belinostat can be increased when it is combined with Tariquidar.
BendamustineThe serum concentration of Bendamustine can be increased when it is combined with Tariquidar.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alkyl aryl ether / Amine / Amino acid or derivatives / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzamide / Benzanilide / Benzoic acid or derivatives
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
J58862DTVD
CAS number
206873-63-4
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

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. [Article]
  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. [Article]
ChemSpider
130650
BindingDB
50075373
ChEMBL
CHEMBL348475
ZINC
ZINC000004214704
PDBe Ligand
R1H
Wikipedia
Tariquidar
PDB Entries
7a6e / 7neq

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedNot AvailableAdvanced Non Small Cell Lung Cancer (NSCLC) / Stage IIIB Non Small Cell Lung Cancer2
2CompletedDiagnosticCancer1
2CompletedTreatmentAdrenal Cortex Neoplasms1
2CompletedTreatmentNeoplasm Cervix / Neoplasms, Lung / Neoplasms, Ovarian / Renal Neoplasms1
2CompletedTreatmentNeoplasms, Breast1
1CompletedTreatmentAdenaocortical Carcinoma / Coldrhood Cancer / Refractory Cancer / Sarcomas / Wilms' tumor1
1CompletedTreatmentBreast Cancer / Cancer / Lung Cancers / Ovarian Cancer1
1TerminatedOtherNeuropathic Pain1
1, 2RecruitingTreatmentNeuropathic Pain1

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

Targets

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Kind
Protein
Organism
Humans
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

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
References
  1. NCATS: Tariquidar [Link]

Drug created at March 19, 2008 16:19 / Updated at February 21, 2021 18:52