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.

Description

Tariquidar is an anthranilic acid derivative that acts as a potent p-glycoprotein drug efflux pump inhibitor. It binds to P-glycoprotein with high affinity (Kd = 5.1 nM) and effectively inhibits its transport activity. Tariquidar's modulating effect is attributed to the inhibition of substrate binding and/or ATP hydrolysis. Tariquidar is particularly useful in the field of cancer research, as it can help elucidate the role of P-glycoprotein inhibition in cancer treatment.

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

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.