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MedKoo Cat#: 562232 | Name: Tariquidar dimesylate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Tariquidar dimesylate
Tariquidar dimesylate
CAS#625375-84-0 (mesylate)

Theoretical Analysis

MedKoo Cat#: 562232

Name: Tariquidar dimesylate

CAS#: 625375-84-0 (mesylate)

Chemical Formula: C40H46N4O12S2

Exact Mass: 0.0000

Molecular Weight: 838.94

Elemental Analysis: C, 57.27; H, 5.53; N, 6.68; O, 22.88; S, 7.64

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
206873-63-4 (free base) 625375-84-0 (mesylate)
Synonym
Tariquidar dimesylate; Tariquidar dimesilate; XR 9576, XR9576, XR-9576, D06008, D 06008, D-06008,
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 dimesylate
InChi Key
FBCFBFPCZHHRMA-UHFFFAOYSA-N
InChi Code
InChI=1S/C38H38N4O6.2CH4O3S/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;2*1-5(2,3)4/h5-12,17-22H,13-16,23H2,1-4H3,(H,40,44)(H,41,43);2*1H3,(H,2,3,4)
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.OS(=O)(C)=O.OS(=O)(C)=O
Appearance
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 838.94 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
1: Joshi P, Vishwakarma RA, Bharate SB. Natural alkaloids as P-gp inhibitors for multidrug resistance reversal in cancer. Eur J Med Chem. 2017 Sep 29;138:273-292. doi: 10.1016/j.ejmech.2017.06.047. Epub 2017 Jun 27. Review. PubMed PMID: 28675836. 2: Lubberink M. Kinetic Models for Measuring P-glycoprotein Function at the Blood-Brain Barrier with Positron Emission Tomography. Curr Pharm Des. 2016;22(38):5786-5792. Review. PubMed PMID: 27494063. 3: Zinzi L, Capparelli E, Cantore M, Contino M, Leopoldo M, Colabufo NA. Small and Innovative Molecules as New Strategy to Revert MDR. Front Oncol. 2014 Jan 21;4:2. doi: 10.3389/fonc.2014.00002. eCollection 2014. Review. PubMed PMID: 24478983; PubMed Central PMCID: PMC3896858. 4: Wanek T, Mairinger S, Langer O. Radioligands targeting P-glycoprotein and other drug efflux proteins at the blood-brain barrier. J Labelled Comp Radiopharm. 2013 Mar-Apr;56(3-4):68-77. doi: 10.1002/jlcr.2993. Review. PubMed PMID: 24285312. 5: Lecerf-Schmidt F, Peres B, Valdameri G, Gauthier C, Winter E, Payen L, Di Pietro A, Boumendjel A. ABCG2: recent discovery of potent and highly selective inhibitors. Future Med Chem. 2013 Jun;5(9):1037-45. doi: 10.4155/fmc.13.71. Review. PubMed PMID: 23734686. 6: Feldmann M, Koepp M. P-glycoprotein imaging in temporal lobe epilepsy: in vivo PET experiments with the Pgp substrate [11C]-verapamil. Epilepsia. 2012 Nov;53 Suppl 6:60-3. doi: 10.1111/j.1528-1167.2012.03704.x. Review. PubMed PMID: 23134497. 7: Palmeira A, Sousa E, Vasconcelos MH, Pinto MM. Three decades of P-gp inhibitors: skimming through several generations and scaffolds. Curr Med Chem. 2012;19(13):1946-2025. Review. PubMed PMID: 22257057. 8: Akhtar N, Ahad A, Khar RK, Jaggi M, Aqil M, Iqbal Z, Ahmad FJ, Talegaonkar S. The emerging role of P-glycoprotein inhibitors in drug delivery: a patent review. Expert Opin Ther Pat. 2011 Apr;21(4):561-76. doi: 10.1517/13543776.2011.561784. Epub 2011 Feb 26. Review. PubMed PMID: 21413912. 9: Colabufo NA, Berardi F, Perrone MG, Capparelli E, Cantore M, Inglese C, Perrone R. Substrates, inhibitors and activators of P-glycoprotein: candidates for radiolabeling and imaging perspectives. Curr Top Med Chem. 2010;10(17):1703-14. Review. PubMed PMID: 20645922. 10: 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. 11: Hughes JR. One of the hottest topics in epileptology: ABC proteins. Their inhibition may be the future for patients with intractable seizures. Neurol Res. 2008 Nov;30(9):920-5. doi: 10.1179/174313208X319116. Epub 2008 Jun 30. Review. PubMed PMID: 18593522. 12: 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. 13: Modok S, Mellor HR, Callaghan R. Modulation of multidrug resistance efflux pump activity to overcome chemoresistance in cancer. Curr Opin Pharmacol. 2006 Aug;6(4):350-4. Epub 2006 May 11. Review. PubMed PMID: 16690355. 14: Ross DD. Modulation of drug resistance transporters as a strategy for treating myelodysplastic syndrome. Best Pract Res Clin Haematol. 2004 Dec;17(4):641-51. Review. PubMed PMID: 15494300. 15: Thomas H, Coley HM. Overcoming multidrug resistance in cancer: an update on the clinical strategy of inhibiting p-glycoprotein. Cancer Control. 2003 Mar-Apr;10(2):159-65. Review. PubMed PMID: 12712010. 16: Bates SF, Chen C, Robey R, Kang M, Figg WD, Fojo T. Reversal of multidrug resistance: lessons from clinical oncology. Novartis Found Symp. 2002;243:83-96; discussion 96-102, 180-5. Review. PubMed PMID: 11990784.