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206873-63-4,MFCD09837824
Catalog No.:AA002IND

206873-63-4 | Tariquidar

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1mg
95%
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$35.00   $24.00
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5mg
95%
in stock  
$78.00   $54.00
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10mg
95%
in stock  
$112.00   $78.00
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25mg
95%
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$180.00   $126.00
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100mg
95%
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$569.00   $398.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002IND
Chemical Name:
Tariquidar
CAS Number:
206873-63-4
Molecular Formula:
C38H38N4O6
Molecular Weight:
646.7315
MDL Number:
MFCD09837824
SMILES:
COc1cc(C(=O)Nc2ccc(cc2)CCN2CCc3c(C2)cc(c(c3)OC)OC)c(cc1OC)NC(=O)c1cnc2c(c1)cccc2
Properties
Properties
 
BP:
716°C at 760 mmHg  
Form:
Solid  
MP:
>190ºC (dec.)  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
1040  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
48  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
11  
XLogP3:
6.1  

Downstream Synthesis Route

[1]CurrentPatentAssignee:AZATRIUSPHARMACEUTICALSPRIVATE-WO2003/95447,2003,A1Locationinpatent:Page/Pagecolumn15-16

[1]Li,Xu-Qin;Wang,Lin;Lei,Yan;Hu,Tao;Zhang,Fei-Long;Cho,Chi-Hin;To,KennethK.W.[EuropeanJournalofMedicinalChemistry,2015,vol.101,p.560-572]

[2]CurrentPatentAssignee:IZUMITECHNOLOGYLLC-US2019/343827,2019,A1Locationinpatent:Paragraph0316-1317

[1]Li,Xu-Qin;Wang,Lin;Lei,Yan;Hu,Tao;Zhang,Fei-Long;Cho,Chi-Hin;To,KennethK.W.[EuropeanJournalofMedicinalChemistry,2015,vol.101,p.560-572]

[1]Li,Xu-Qin;Wang,Lin;Lei,Yan;Hu,Tao;Zhang,Fei-Long;Cho,Chi-Hin;To,KennethK.W.[EuropeanJournalofMedicinalChemistry,2015,vol.101,p.560-572]

Literature

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Journal: Toxicological sciences : an official journal of the Society of Toxicology 20180701

Title: Increasing nerve agent treatment efficacy by P-glycoprotein inhibition.

Journal: Chemico-biological interactions 20161125

Title: Inhibition of P-glycoprotein Gene Expression and Function Enhances Triptolide-induced Hepatotoxicity in Mice.

Journal: Scientific reports 20150101

Title: Behavioral effects and central nervous system levels of the broadly available κ-agonist hallucinogen salvinorin A are affected by P-glycoprotein modulation in vivo.

Journal: The Journal of pharmacology and experimental therapeutics 20120601

Title: Structure-activity relationships, ligand efficiency, and lipophilic efficiency profiles of benzophenone-type inhibitors of the multidrug transporter P-glycoprotein.

Journal: Journal of medicinal chemistry 20120412

Title: [Evaluation of P-glycoprotein mediated in vitro loperamide biliary excretion with sandwich-cultured rat hepatocytes model].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20120401

Title: Alteration in P-glycoprotein functionality affects intrabrain distribution of quinidine more than brain entry-a study in rats subjected to status epilepticus by kainate.

Journal: The AAPS journal 20120301

Title: Pgp-mediated interaction between (R)-[11C]verapamil and tariquidar at the human blood-brain barrier: a comparison with rat data.

Journal: Clinical pharmacology and therapeutics 20120201

Title: A comparative small-animal PET evaluation of [11C]tariquidar, [11C]elacridar and (R)-[11C]verapamil for detection of P-glycoprotein-expressing murine breast cancer.

Journal: European journal of nuclear medicine and molecular imaging 20120101

Title: Genetic knockdown and pharmacological inhibition of parasite multidrug resistance transporters disrupts egg production in Schistosoma mansoni.

Journal: PLoS neglected tropical diseases 20111201

Title: Increasing oxime efficacy by blood-brain barrier modulation.

Journal: Toxicology letters 20110925

Title: Synthesis and structure-activity evaluation of isatin-β-thiosemicarbazones with improved selective activity toward multidrug-resistant cells expressing P-glycoprotein.

Journal: Journal of medicinal chemistry 20110825

Title: Collateral sensitivity of multidrug-resistant cells to the orphan drug tiopronin.

Journal: Journal of medicinal chemistry 20110728

Title: Solid phase synthesis of tariquidar-related modulators of ABC transporters preferring breast cancer resistance protein (ABCG2).

Journal: Bioorganic & medicinal chemistry letters 20110615

Title: A novel positron emission tomography imaging protocol identifies seizure-induced regional overactivity of P-glycoprotein at the blood-brain barrier.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20110615

Title: The third-generation P-glycoprotein inhibitor tariquidar may overcome bacterial multidrug resistance by increasing intracellular drug concentration.

Journal: The Journal of antimicrobial chemotherapy 20110401

Title: Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).

Journal: Bioorganic & medicinal chemistry 20110315

Title: A pharmacodynamic study of docetaxel in combination with the P-glycoprotein antagonist tariquidar (XR9576) in patients with lung, ovarian, and cervical cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20110201

Title: Synthesis and in vivo evaluation of ¹⁸F-fluoroethyl GF120918 and XR9576 as positron emission tomography probes for assessing the function of drug efflux transporters.

Journal: Bioorganic & medicinal chemistry 20110115

Title: Specific inhibitors of the breast cancer resistance protein (BCRP).

Journal: ChemMedChem 20100903

Title: Synthesis and evaluation of [11C]XR9576 to assess the function of drug efflux transporters using PET.

Journal: Annals of nuclear medicine 20100601

Title: Dose-response assessment of tariquidar and elacridar and regional quantification of P-glycoprotein inhibition at the rat blood-brain barrier using (R)-[(11)C]verapamil PET.

Journal: European journal of nuclear medicine and molecular imaging 20100501

Title: P-glycoprotein function at the blood-brain barrier in humans can be quantified with the substrate radiotracer 11C-N-desmethyl-loperamide.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20100401

Title: Assessment of regional differences in tariquidar-induced P-glycoprotein modulation at the human blood-brain barrier.

Journal: Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20100301

Title: Uptake and binding of the serotonin 5-HT1A antagonist [18F]-MPPF in brain of rats: effects of the novel P-glycoprotein inhibitor tariquidar.

Journal: NeuroImage 20100115

Title: Novel lead for potent inhibitors of breast cancer resistance protein (BCRP).

Journal: Bioorganic & medicinal chemistry letters 20100101

Title: A pilot study to assess the efficacy of tariquidar to inhibit P-glycoprotein at the human blood-brain barrier with (R)-11C-verapamil and PET.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20091201

Title: Nanoparticle-mediated simultaneous and targeted delivery of paclitaxel and tariquidar overcomes tumor drug resistance.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20090521

Title: A phase I study of the P-glycoprotein antagonist tariquidar in combination with vinorelbine.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090515

Title: Synthesis and biological evaluation of a small molecule library of 3rd generation multidrug resistance modulators.

Journal: Bioorganic & medicinal chemistry 20090315

Title: Potent and selective inhibitors of breast cancer resistance protein (ABCG2) derived from the p-glycoprotein (ABCB1) modulator tariquidar.

Journal: Journal of medicinal chemistry 20090226

Title: Functional and energetic characterization of P-gp-mediated doxorubicin transport in rainbow trout (Oncorhynchus mykiss) hepatocytes.

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20090101

Title: Influence of the dual ABCB1 and ABCG2 inhibitor tariquidar on the disposition of oral imatinib in mice.

Journal: Journal of experimental & clinical cancer research : CR 20090101

Title: Tariquidar, a selective P-glycoprotein inhibitor, does not potentiate loperamide's opioid brain effects in humans despite full inhibition of lymphocyte P-glycoprotein.

Journal: Anesthesiology 20081201

Title: Resistance to antiepileptic drugs and expression of P-glycoprotein in two rat models of status epilepticus.

Journal: Epilepsy research 20081101

Title: Tariquidar-induced P-glycoprotein inhibition at the rat blood-brain barrier studied with (R)-11C-verapamil and PET.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20080801

Title: Effect of the ABCB1 modulators elacridar and tariquidar on the distribution of paclitaxel in nude mice.

Journal: Journal of cancer research and clinical oncology 20080501

Title: Glutamate is critically involved in seizure-induced overexpression of P-glycoprotein in the brain.

Journal: Neuropharmacology 20080501

Title: Inhibition of P-glycoprotein (ABCB1)- and multidrug resistance-associated protein 1 (ABCC1)-mediated transport by the orally administered inhibitor, CBT-1((R)).

Journal: Biochemical pharmacology 20080315

Title: Functional assay and structure-activity relationships of new third-generation P-glycoprotein inhibitors.

Journal: Bioorganic & medicinal chemistry 20080301

Title: Small P-gp modulating molecules: SAR studies on tetrahydroisoquinoline derivatives.

Journal: Bioorganic & medicinal chemistry 20080101

Title: Region-specific overexpression of P-glycoprotein at the blood-brain barrier affects brain uptake of phenytoin in epileptic rats.

Journal: The Journal of pharmacology and experimental therapeutics 20070701

Title: In vitro activity of novel dual action MDR anthranilamide modulators with inhibitory activity on CYP-450 (Part 2).

Journal: Bioorganic & medicinal chemistry 20070601

Title: Differential drug susceptibility of intracellular and extracellular tuberculosis, and the impact of P-glycoprotein.

Journal: Tuberculosis (Edinburgh, Scotland) 20070501

Title: Development of a humanized in vitro blood-brain barrier model to screen for brain penetration of antiepileptic drugs.

Journal: Epilepsia 20070301

Title: Differences in the transport of the antiepileptic drugs phenytoin, levetiracetam and carbamazepine by human and mouse P-glycoprotein.

Journal: Neuropharmacology 20070201

Title: Multidrug-resistance gene 1-type p-glycoprotein (MDR1 p-gp) inhibition by tariquidar impacts on neuroendocrine and behavioral processing of stress.

Journal: Psychoneuroendocrinology 20070101

Title: In vitro activity of novel dual action MDR anthranilamide modulators with inhibitory activity at CYP-450.

Journal: Bioorganic & medicinal chemistry 20061201

Title: Quantification of serotonin 5-HT1A receptors in monkey brain with [11C](R)-(-)-RWAY.

Journal: Synapse (New York, N.Y.) 20061201

Title: The erythromycin breath test reflects P-glycoprotein function independently of cytochrome P450 3A activity.

Journal: Clinical pharmacology and therapeutics 20060901

Title: Modulation of multidrug resistance efflux pump activity to overcome chemoresistance in cancer.

Journal: Current opinion in pharmacology 20060801

Title: Differential in vivo sensitivity to inhibition of P-glycoprotein located in lymphocytes, testes, and the blood-brain barrier.

Journal: The Journal of pharmacology and experimental therapeutics 20060601

Title: Inhibition of multidrug resistance transporter-1 facilitates neuroprotective therapies after focal cerebral ischemia.

Journal: Nature neuroscience 20060401

Title: Inhibition of the multidrug transporter P-glycoprotein improves seizure control in phenytoin-treated chronic epileptic rats.

Journal: Epilepsia 20060401

Title: Structure-activity relationships of a series of tariquidar analogs as multidrug resistance modulators.

Journal: Bioorganic & medicinal chemistry 20060301

Title: Phase II study of tariquidar, a selective P-glycoprotein inhibitor, in patients with chemotherapy-resistant, advanced breast carcinoma.

Journal: Cancer 20050815

Title: Identification of OATP1B3 as a high-affinity hepatocellular transporter of paclitaxel.

Journal: Cancer biology & therapy 20050801

Title: The coupling mechanism of P-glycoprotein involves residue L339 in the sixth membrane spanning segment.

Journal: FEBS letters 20050718

Title: Modulation of drug resistance transporters as a strategy for treating myelodysplastic syndrome.

Journal: Best practice & research. Clinical haematology 20041201

Title: P-glycoprotein retains function when reconstituted into a sphingolipid- and cholesterol-rich environment.

Journal: Journal of lipid research 20041001

Title: Ex vivo reversal of chemoresistance by tariquidar (XR9576).

Journal: Anti-cancer drugs 20041001

Title: Inhibition of glucosylceramide synthase does not reverse drug resistance in cancer cells.

Journal: The Journal of biological chemistry 20040924

Title: Inhibition of P-glycoprotein function by XR9576 in a solid tumour model can restore anticancer drug efficacy.

Journal: European journal of cancer (Oxford, England : 1990) 20040301

Title: Pheophorbide a is a specific probe for ABCG2 function and inhibition.

Journal: Cancer research 20040215

Title: Pumping of drugs by P-glycoprotein: a two-step process?

Journal: The Journal of pharmacology and experimental therapeutics 20031201

Title: The histone deacetylase inhibitor FK228 preferentially enhances adenovirus transgene expression in malignant cells.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20031101

Title: Increased 99mTc-sestamibi accumulation in normal liver and drug-resistant tumors after the administration of the glycoprotein inhibitor, XR9576.

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Title: In vitro prevention of the emergence of multidrug resistance in a pediatric rhabdomyosarcoma cell line.

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Title: Zimmermann ES, et al. Simultaneous Semimechanistic Population Analyses of Levofloxacin in Plasma, Lung, and Prostate To Describe the Influence of Efflux Transporters on Drug Distribution following Intravenous and Intratracheal Administration. Antimicrob Agents Chemother. 2015 Nov 30;60(2):946-54.

Title: Kao YH, et al. Regulation of P-glycoprotein expression in brain capillaries in Huntington's disease and its impact on brain availability of antipsychotic agents risperidone and paliperidone. J Cereb Blood Flow Metab. 2016 Aug;36(8):1412-23.

Title: Matzneller P, et al. Pharmacokinetics of the P-gp Inhibitor Tariquidar in Rats After Intravenous, Oral, and Intraperitoneal Administration. Eur J Drug Metab Pharmacokinet. 2018 Apr 3.

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