Tariquidar
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MedKoo CAT#: 202820

CAS#: 206873-63-4 (free base)

Description: Tariquidar, also known as XR9576, is a P-glycoprotein (P-gp) inhibitor undergoing research as an adjuvant against multidrug resistance in cancer. Tariquidar non-competitively binds to the p-glycoprotein transporter, thereby inhibiting transmembrane transport of anticancer drugs. Inhibition of transmembrane transport may result in increased intracellular concentrations of an anticancer drug, thereby augmenting its cytotoxicity.


Chemical Structure

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Tariquidar
CAS# 206873-63-4 (free base)

Theoretical Analysis

MedKoo Cat#: 202820
Name: Tariquidar
CAS#: 206873-63-4 (free base)
Chemical Formula: C38H38N4O6
Exact Mass: 646.27913
Molecular Weight: 646.73
Elemental Analysis: C, 70.57; H, 5.92; N, 8.66; O, 14.84

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Related CAS #: 206873-63-4 (free base)   625375-84-0 (mesylate)    

Synonym: XR 9576, XR9576, XR-9576, D06008, D 06008, D-06008, Tariquidar

IUPAC/Chemical Name: N-[2-[[4-[2-(6,7-Dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]-4,5-dimethoxyphenyl]quinoline-3-carboxamide

InChi Key: LGGHDPFKSSRQNS-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(C1=CC2=CC=CC=C2N=C1)NC3=CC(OC)=C(OC)C=C3C(NC4=CC=C(CCN5CC6=C(C=C(OC)C(OC)=C6)CC5)C=C4)=O

Appearance: light yellow solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 646.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Pajeva IK, Sterz K, Christlieb M, Steggemann K, Marighetti F, Wiese M. Interactions of the Multidrug Resistance Modulators Tariquidar and Elacridar and their Analogues with P-glycoprotein. ChemMedChem. 2013 Aug 13. doi: 10.1002/cmdc.201300233. [Epub ahead of print] PubMed PMID: 23943604.

2: Bauer M, Karch R, Zeitlinger M, Stanek J, Philippe C, Wadsak W, Mitterhauser M, Jäger W, Haslacher H, Müller M, Langer O. Interaction of 11C-tariquidar and 11C-elacridar with P-glycoprotein and breast cancer resistance protein at the human blood-brain barrier. J Nucl Med. 2013 Aug;54(8):1181-7. doi: 10.2967/jnumed.112.118232. Epub 2013 Jul 5. PubMed PMID: 23833270.

3: Contino M, Zinzi L, Cantore M, Perrone MG, Leopoldo M, Berardi F, Perrone R, Colabufo NA. Activity-lipophilicity relationship studies on P-gp ligands designed as simplified tariquidar bulky fragments. Bioorg Med Chem Lett. 2013 Jul 1;23(13):3728-31. doi: 10.1016/j.bmcl.2013.05.019. Epub 2013 May 16. PubMed PMID: 23726026.

4: Sun YL, Chen JJ, Kumar P, Chen K, Sodani K, Patel A, Chen YL, Chen SD, Jiang WQ, Chen ZS. Reversal of MRP7 (ABCC10)-mediated multidrug resistance by tariquidar. PLoS One. 2013;8(2):e55576. doi: 10.1371/journal.pone.0055576. Epub 2013 Feb 5. PubMed PMID: 23393594; PubMed Central PMCID: PMC3564796.

5: Contino M, Zinzi L, Perrone MG, Leopoldo M, Berardi F, Perrone R, Colabufo NA. Potent and selective tariquidar bioisosters as potential PET radiotracers for imaging P-gp. Bioorg Med Chem Lett. 2013 Mar 1;23(5):1370-4. doi: 10.1016/j.bmcl.2012.12.084. Epub 2013 Jan 5. PubMed PMID: 23374872.

6: Bankstahl JP, Bankstahl M, Römermann K, Wanek T, Stanek J, Windhorst AD, Fedrowitz M, Erker T, Müller M, Löscher W, Langer O, Kuntner C. Tariquidar and elacridar are dose-dependently transported by P-glycoprotein and Bcrp at the blood-brain barrier: a small-animal positron emission tomography and in vitro study. Drug Metab Dispos. 2013 Apr;41(4):754-62. doi: 10.1124/dmd.112.049148. Epub 2013 Jan 10. PubMed PMID: 23305710.

7: Bauer M, Zeitlinger M, Todorut D, Böhmdorfer M, Müller M, Langer O, Jäger W. Pharmacokinetics of single ascending doses of the P-glycoprotein inhibitor tariquidar in healthy subjects. Pharmacology. 2013;91(1-2):12-9. doi: 10.1159/000343243. Epub 2012 Nov 7. PubMed PMID: 23146816; PubMed Central PMCID: PMC3689924.

8: Bauer M, Zeitlinger M, Karch R, Matzneller P, Stanek J, Jäger W, Böhmdorfer M, Wadsak W, Mitterhauser M, Bankstahl JP, Löscher W, Koepp M, Kuntner C, Müller M, Langer O. Pgp-mediated interaction between (R)-[11C]verapamil and tariquidar at the human blood-brain barrier: a comparison with rat data. Clin Pharmacol Ther. 2012 Feb;91(2):227-33. doi: 10.1038/clpt.2011.217. Epub 2011 Dec 14. PubMed PMID: 22166851; PubMed Central PMCID: PMC3685270.

9: Wanek T, Kuntner C, Bankstahl JP, Bankstahl M, Stanek J, Sauberer M, Mairinger S, Strommer S, Wacheck V, Löscher W, Erker T, Müller M, Langer O. A comparative small-animal PET evaluation of [11C]tariquidar, [11C]elacridar and (R)-[11C]verapamil for detection of P-glycoprotein-expressing murine breast cancer. Eur J Nucl Med Mol Imaging. 2012 Jan;39(1):149-59. doi: 10.1007/s00259-011-1941-7. Epub 2011 Oct 8. PubMed PMID: 21983837; PubMed Central PMCID: PMC3684861.

10: Patel NR, Rathi A, Mongayt D, Torchilin VP. Reversal of multidrug resistance by co-delivery of tariquidar (XR9576) and paclitaxel using long-circulating liposomes. Int J Pharm. 2011 Sep 15;416(1):296-9. doi: 10.1016/j.ijpharm.2011.05.082. Epub 2011 Jun 15. PubMed PMID: 21703341; PubMed Central PMCID: PMC3156341.

11: Puentes CO, Höcherl P, Kühnle M, Bauer S, Bürger K, Bernhardt G, Buschauer A, König B. Solid phase synthesis of tariquidar-related modulators of ABC transporters preferring breast cancer resistance protein (ABCG2). Bioorg Med Chem Lett. 2011 Jun 15;21(12):3654-7. doi: 10.1016/j.bmcl.2011.04.094. Epub 2011 Apr 28. PubMed PMID: 21570282.

12: Leitner I, Nemeth J, Feurstein T, Abrahim A, Matzneller P, Lagler H, Erker T, Langer O, Zeitlinger M. The third-generation P-glycoprotein inhibitor tariquidar may overcome bacterial multidrug resistance by increasing intracellular drug concentration. J Antimicrob Chemother. 2011 Apr;66(4):834-9. doi: 10.1093/jac/dkq526. Epub 2011 Jan 19. PubMed PMID: 21393173.

13: Kannan P, Telu S, Shukla S, Ambudkar SV, Pike VW, Halldin C, Gottesman MM, Innis RB, Hall MD. The "specific" P-glycoprotein inhibitor Tariquidar is also a substrate and an inhibitor for breast cancer resistance protein (BCRP/ABCG2). ACS Chem Neurosci. 2011 Feb 16;2(2):82-9. doi: 10.1021/cn100078a. Epub 2010 Oct 21. PubMed PMID: 22778859; PubMed Central PMCID: PMC3369725.

14: Kelly RJ, Draper D, Chen CC, Robey RW, Figg WD, Piekarz RL, Chen X, Gardner ER, Balis FM, Venkatesan AM, Steinberg SM, Fojo T, Bates SE. A pharmacodynamic study of docetaxel in combination with the P-glycoprotein antagonist tariquidar (XR9576) in patients with lung, ovarian, and cervical cancer. Clin Cancer Res. 2011 Feb 1;17(3):569-80. doi: 10.1158/1078-0432.CCR-10-1725. Epub 2010 Nov 16. PubMed PMID: 21081657; PubMed Central PMCID: PMC3071989.

15: Bauer F, Kuntner C, Bankstahl JP, Wanek T, Bankstahl M, Stanek J, Mairinger S, Dörner B, Löscher W, Müller M, Erker T, Langer O. Synthesis and in vivo evaluation of [11C]tariquidar, a positron emission tomography radiotracer based on a third-generation P-glycoprotein inhibitor. Bioorg Med Chem. 2010 Aug 1;18(15):5489-97. doi: 10.1016/j.bmc.2010.06.057. Epub 2010 Jun 22. PubMed PMID: 20621487; PubMed Central PMCID: PMC3690440.

16: Wang M, Zheng DX, Luo MB, Gao M, Miller KD, Hutchins GD, Zheng QH. Synthesis of carbon-11-labeled tariquidar derivatives as new PET agents for imaging of breast cancer resistance protein (ABCG2). Appl Radiat Isot. 2010 Jun;68(6):1098-103. doi: 10.1016/j.apradiso.2010.02.008. Epub 2010 Feb 13. PubMed PMID: 20181488.

17: Kuntner C, Bankstahl JP, Bankstahl M, Stanek J, Wanek T, Stundner G, Karch R, Brauner R, Meier M, Ding X, Müller M, Löscher W, Langer O. 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. Eur J Nucl Med Mol Imaging. 2010 May;37(5):942-53. doi: 10.1007/s00259-009-1332-5. Epub 2009 Dec 17. PubMed PMID: 20016890; PubMed Central PMCID: PMC3690672.

18: Bauer M, Karch R, Neumann F, Wagner CC, Kletter K, Müller M, Löscher W, Zeitlinger M, Langer O. Assessment of regional differences in tariquidar-induced P-glycoprotein modulation at the human blood-brain barrier. J Cereb Blood Flow Metab. 2010 Mar;30(3):510-5. doi: 10.1038/jcbfm.2009.265. Epub 2009 Dec 16. PubMed PMID: 20010957; PubMed Central PMCID: PMC2949150.

19: Wagner CC, Bauer M, Karch R, Feurstein T, Kopp S, Chiba P, Kletter K, Löscher W, Müller M, Zeitlinger M, Langer O. 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. J Nucl Med. 2009 Dec;50(12):1954-61. doi: 10.2967/jnumed.109.063289. Epub 2009 Nov 12. PubMed PMID: 19910428; PubMed Central PMCID: PMC3690436.

20: la Fougère C, Böning G, Bartmann H, Wängler B, Nowak S, Just T, Wagner E, Winter P, Rominger A, Förster S, Gildehaus FJ, Rosa-Neto P, Minuzzi L, Bartenstein P, Potschka H, Cumming P. Uptake and binding of the serotonin 5-HT1A antagonist [18F]-MPPF in brain of rats: effects of the novel P-glycoprotein inhibitor tariquidar. Neuroimage. 2010 Jan 15;49(2):1406-15. doi: 10.1016/j.neuroimage.2009.09.048. Epub 2009 Sep 28. PubMed PMID: 19796699.

21: Gardner ER, Smith NF, Figg WD, Sparreboom A. Influence of the dual ABCB1 and ABCG2 inhibitor tariquidar on the disposition of oral imatinib in mice. J Exp Clin Cancer Res. 2009 Jul 10;28:99. doi: 10.1186/1756-9966-28-99. PubMed PMID: 19591692; PubMed Central PMCID: PMC2717937.

22: Pajeva IK, Wiese M. Structure-activity relationships of tariquidar analogs as multidrug resistance modulators. AAPS J. 2009 Sep;11(3):435-44. doi: 10.1208/s12248-009-9118-z. Epub 2009 Jun 6. Review. PubMed PMID: 19504188; PubMed Central PMCID: PMC2758111.

23: Abraham J, Edgerly M, Wilson R, Chen C, Rutt A, Bakke S, Robey R, Dwyer A, Goldspiel B, Balis F, Van Tellingen O, Bates SE, Fojo T. A phase I study of the P-glycoprotein antagonist tariquidar in combination with vinorelbine. Clin Cancer Res. 2009 May 15;15(10):3574-82. doi: 10.1158/1078-0432.CCR-08-0938. Epub 2009 May 5. PubMed PMID: 19417029.

24: Patil Y, Sadhukha T, Ma L, Panyam J. Nanoparticle-mediated simultaneous and targeted delivery of paclitaxel and tariquidar overcomes tumor drug resistance. J Control Release. 2009 May 21;136(1):21-9. doi: 10.1016/j.jconrel.2009.01.021. Epub 2009 Feb 5. PubMed PMID: 19331851.

25: Kühnle M, Egger M, Müller C, Mahringer A, Bernhardt G, Fricker G, König B, Buschauer A. Potent and selective inhibitors of breast cancer resistance protein (ABCG2) derived from the p-glycoprotein (ABCB1) modulator tariquidar. J Med Chem. 2009 Feb 26;52(4):1190-7. doi: 10.1021/jm8013822. PubMed PMID: 19170519.

26: Kurnik D, Sofowora GG, Donahue JP, Nair UB, Wilkinson GR, Wood AJ, Muszkat M. Tariquidar, a selective P-glycoprotein inhibitor, does not potentiate loperamide's opioid brain effects in humans despite full inhibition of lymphocyte P-glycoprotein. Anesthesiology. 2008 Dec;109(6):1092-9. doi: 10.1097/ALN.0b013e31818d8f28. PubMed PMID: 19034106.

27: Bankstahl JP, Kuntner C, Abrahim A, Karch R, Stanek J, Wanek T, Wadsak W, Kletter K, Müller M, Löscher W, Langer O. Tariquidar-induced P-glycoprotein inhibition at the rat blood-brain barrier studied with (R)-11C-verapamil and PET. J Nucl Med. 2008 Aug;49(8):1328-35. doi: 10.2967/jnumed.108.051235. Epub 2008 Jul 16. PubMed PMID: 18632828; PubMed Central PMCID: PMC3690700.

28: Hubensack M, Müller C, Höcherl P, Fellner S, Spruss T, Bernhardt G, Buschauer A. Effect of the ABCB1 modulators elacridar and tariquidar on the distribution of paclitaxel in nude mice. J Cancer Res Clin Oncol. 2008 May;134(5):597-607. Epub 2007 Oct 12. PubMed PMID: 17932689.

29: Thoeringer CK, Wultsch T, Shahbazian A, Painsipp E, Holzer P. Multidrug-resistance gene 1-type p-glycoprotein (MDR1 p-gp) inhibition by tariquidar impacts on neuroendocrine and behavioral processing of stress. Psychoneuroendocrinology. 2007 Sep-Nov;32(8-10):1028-40. Epub 2007 Sep 19. PubMed PMID: 17881135.

30: Fox E, Bates SE. Tariquidar (XR9576): a P-glycoprotein drug efflux pump inhibitor. Expert Rev Anticancer Ther. 2007 Apr;7(4):447-59. Review. PubMed PMID: 17428165.

31: Globisch C, Pajeva IK, Wiese M. Structure-activity relationships of a series of tariquidar analogs as multidrug resistance modulators. Bioorg Med Chem. 2006 Mar 1;14(5):1588-98. Epub 2005 Nov 22. PubMed PMID: 16307883.

32: Pusztai L, Wagner P, Ibrahim N, Rivera E, Theriault R, Booser D, Symmans FW, Wong F, Blumenschein G, Fleming DR, Rouzier R, Boniface G, Hortobagyi GN. Phase II study of tariquidar, a selective P-glycoprotein inhibitor, in patients with chemotherapy-resistant, advanced breast carcinoma. Cancer. 2005 Aug 15;104(4):682-91. PubMed PMID: 15986399.

33: Di Nicolantonio F, Knight LA, Glaysher S, Whitehouse PA, Mercer SJ, Sharma S, Mills L, Prin A, Johnson P, Charlton PA, Norris D, Cree IA. Ex vivo reversal of chemoresistance by tariquidar (XR9576). Anticancer Drugs. 2004 Oct;15(9):861-9. PubMed PMID: 15457126.