206873-63-4

Basic information

• Product Name: Tariquidar
• Synonyms: N-[2-[[4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl]carbamoyl]-4,5-dimethoxy-phenyl]quinoline-3-carboxamide;Tariquidar;3-Quinolinecarboxamide, N-(2-(((4-(2-(3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl)phenyl)amino)carbonyl)-4,5-dimethoxyphenyl)-;N-(2-((4-(2-(6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethyl)phenyl)carbamoyl)-4,5-dimethoxyphenyl)quinoline-3-carboxamide;Unii-J58862dtvd;Xr 9576;Xr9576;N-[2-[N-[4-[2-(6,7-DiMethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]phenyl]carbaMoyl]-4,5-diMethoxyphenyl]quinoline-3-carboxaMide
• CAS NO: 206873-63-4
• Molecular Formula: C38H38N4O6
• Molecular Weight: 646.73
• Product Categories: Inhibitor;Anti-cancer&immunity;Inhibitors
• Mol File: 206873-63-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 716°Cat760mmHg
• Flash Point: 386.8°C
• Appearance: /
• Density: 1.276g/cm³
• Vapor Pressure: 2.37E-20mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.67±0.70(Predicted)
• CAS DataBase Reference: Tariquidar(CAS DataBase Reference)
• NIST Chemistry Reference: Tariquidar(206873-63-4)
• EPA Substance Registry System: Tariquidar(206873-63-4)

Safety Data

• Hazardous Substances Data: 206873-63-4(Hazardous Substances Data)

Usage

Chemical Description

Tariquidar is a drug used to treat cancer.

Uses

Used in Cancer Research:
Tariquidar is used as a p-glycoprotein inhibitor for cancer research, specifically to investigate the role of P-glycoprotein inhibition in cancer treatment. By inhibiting the ATPase activity of P-glycoprotein, Tariquidar can modulate the transport of chemotherapeutic drugs, potentially enhancing their efficacy and overcoming multidrug resistance in cancer cells.
Used in Drug Delivery Systems:
Tariquidar is used as a modulator in drug delivery systems to improve the distribution and bioavailability of its substrates. It has been shown to increase the steady-state accumulation of drugs like vinblastine and paclitaxel in multidrug-resistant cells, effectively raising their levels to those observed in non-P-glycoprotein-expressing, multidrug-sensitive cells. Additionally, Tariquidar enhances the distribution of its substrates into the central nervous system (CNS), as demonstrated by its ability to increase the latency to paw withdrawal in a hot plate assay when administered with the peripherally-restricted opioid loperamide.

Biochem/physiol Actions

Specific inhibitor of MDR-1 (P-gp)

InChI:InChI=1/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)

Upstream product

• 82925-02-8 4-<2-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolyl)ethyl>benzenamine 
• 82925-01-7 1,2,3,4-Tetrahydro-6,7-dimethoxy-2-[2-(4-nitrophenyl)ethyl]-isoquinoline 
• 5339-26-4 (4-nitrophenyl)ethyl bromide 
• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 29568-78-3 4,5-dimethoxy-2-nitrobenzoyl chloride 
• 6480-68-8 quinoline-3-carboxylic acid 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 849668-91-3 2-amino-N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-4,5-dimethoxybenzamide 
• 84741-86-6 quinoline-3-carbonyl chloride 

Relevant articles and documents

DEUTERATED ANALOGS OF TARIQUIDAR

The present invention relates to efflux inhibitor compounds, compositions, and methods of using the same. More specifically, the instant invention comprises deuterated analogs of tariquidar with superior pharmacokinetic properties such that it is now poss

Reversal of P-gp and BCRP-mediated MDR by tariquidar derivatives

Abstract With an aim to generate non-toxic, specific and highly potent multidrug resistance (MDR) modulators, a novel series of anthranilic acid amide-substituted tariquidar derivatives were synthesized. The new compounds were evaluated for their cytotoxicity toward normal human colon fibroblasts (CCD18-Co), human gastric epithelial cell line (HFE) and primary rat liver cells, and for their ability to inhibit P-gp/BCRP-mediated drug efflux and reversal of P-gp and BCRP-mediated MDR in parental and drug-resistant cancer cell lines (LCC6 MDR1, MCF-7 FLV1000, R-HepG2, SW620-Ad300). While tariquidar is highly toxic to normal cells, the new derivatives exhibited much lower or negligible cytotoxicity. Some of the new tariquidar derivatives inhibited both P-gp and BCRP-mediated drug efflux whereas a few of them bearing a sulfonamide functional group (1, 5, and 16) are specific to P-gp. The new compounds were also found to potentiate the anticancer activity of the transporter substrate anticancer drugs in the corresponding transporter-overexpressing cell lines. The extent of resistance reversal was found to be consistent with the transporter inhibitory effect of the new derivatives. To further understand the mechanism of P-gp and BCRP inhibition, the tariquidar derivatives were found to interact with the transporters using an antibody-based UIC2 or 5D3 shift assay. Moreover, the transporters-inhibiting derivatives were found to modulate the ATPase activities of the two MDR transporters. Our data thus advocate further development of the new compounds for the circumvention of MDR.

Anthranilic acid derivatives as multi drug resistance modulators

Anthranilic acids of formula (I): wherein each of R to R9is an organic substituent, n is 0 or 1, m is 0 or an integer of 1 to 6, q is 0 or 1, X is a direct bond, O, S, —S—(CH2)por —O—(CHO2)p— wherein p is from 1 to 6 and Ar is an unsaturated carbocyclic or heterocyclic group, and the pharmaceutically acceptable salts thereof, have activity as inhibitors of P-glycoprotein and may thus be used, inter alia, as modulators of multidrug resistance in the treatment of multidrug resistant cancers, for example to potentiate the cytotoxicity of a cancer drug.