Tariquidar

Base Information

• Chemical Name: Tariquidar
• CAS No.: 206873-63-4
• Molecular Formula: C₃₈H₃₈N₄O₆
• Molecular Weight: 646.743
• Hs Code.: 2933499090
• UNII: J58862DTVD
• DSSTox Substance ID: DTXSID10174746
• Nikkaji Number: J1.060.504K
• Wikipedia: Tariquidar
• Wikidata: Q7686198
• NCI Thesaurus Code: C2246
• Pharos Ligand ID: AS2BF9PTQFJX
• Metabolomics Workbench ID: 149697
• ChEMBL ID: CHEMBL348475
• Mol file: 206873-63-4.mol

Synonyms:tariquidar;tariquidarth;XR 9576;XR9576

Chemical Property of Tariquidar

Chemical Property:

• Vapor Pressure: 2.37E-20mmHg at 25°C
• Boiling Point: 716°Cat760mmHg
• PKA: 10.67±0.70(Predicted)
• Flash Point: 386.8°C
• PSA: 111.25000
• Density: 1.276g/cm³
• LogP: 6.45850
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 646.27913494
• Heavy Atom Count: 48
• Complexity: 1040

Purity/Quality:

99% ^*data from raw suppliers

Tariquidar ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2CN(CCC2=C1)CCC3=CC=C(C=C3)NC(=O)C4=CC(=C(C=C4NC(=O)C5=CC6=CC=CC=C6N=C5)OC)OC)OC
• Recent ClinicalTrials: Phase I Trial of Tariquidar (XR9576) in Combination With Doxorubicin, Vinorelbine, or Docetaxel in Pediatric Patients With Solid Tumors
• Recent EU Clinical Trials: A pilot study to assess the influence of drug transporters on brain and organ distribution of erlotinib in humans
• Description: Tariquidar is an anthranilic acid derivative that binds to P-glycoprotein (Kd = 5.1 nM) and inhibits transport activity. It inhibits transport of vinblastine and paclitaxel in multidrug resistant CHrB30 cells, increasing the steady state accumulation to non-P-glycoprotein-expressing multidrug sensitive cell levels (EC50 = 487 nM). Tariquidar also enhances the distribution of its substrates, increasing the amount of substrate entering the CNS. When administered at doses of 2 and 6.25 mg/kg in mice in combination with the peripherally-restricted opioid loperamide, the latency to paw withdrawal in a hot plate assay increases, indicating that loperamide is transported into the CNS.
• Uses: Tariquidar is a p-glycoprotein drug efflux pump inhibitor. Tariquidar inhibits the ATPase activity of P-glycoprotein, suggesting that the modulating effect is derived from the inhibition of substrate binding, inhibition of ATP hydrolysis or both.Tariquidar can be considered an ideal agent for testing the role of P-glycoprotein inhibition in cancer Tariquidar is a p-glycoprotein drug efflux pump inhibitor. Tariquidar inhibits the ATPase activity of P-glycoprotein, suggesting that the modulating effect is derived from the inhibition of substrate binding, inhibition of ATP hydrolysis or both.Tariquidar can be considered an ideal agent for testing the role of P-glycoprotein inhibition in cancer.

Technology Process of Tariquidar

There total 9 articles about Tariquidar which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

2-amino-N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-4,5-dimethoxybenzamide (849668-91-3) + quinoline-3-carbonyl chloride (84741-86-6) → tariquidar (206873-63-4)

Guidance literature:

In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2015.06.049

Reference yield:

4,5-dimethoxy-2-nitro-benzoic acid (4998-07-6) → tariquidar (206873-63-4)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 83 °C

2: sodium hydrogencarbonate / dichloromethane / 5 h / 0 - 20 °C

3: palladium 10% on activated carbon; ammonium formate; hydrogen / methanol / 4 h / Reflux

4: dichloromethane / 24 h / 20 °C

With thionyl chloride; palladium 10% on activated carbon; hydrogen; ammonium formate; sodium hydrogencarbonate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2015.06.049

Reference yield:

quinoline-3-carboxylic acid (6480-68-8) → tariquidar (206873-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 83 °C

2: dichloromethane / 24 h / 20 °C

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2015.06.049

upstream raw materials:

2-amino-N-{4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl]-phenyl}-4,5-dimethoxybenzamide

quinoline-3-carbonyl chloride

4,5-dimethoxy-2-nitro-benzoic acid

quinoline-3-carboxylic acid

Refernces

• 1、 Li, Xu-Qin,Wang, Lin,Lei, Yan,Hu, Tao,Zhang, Fei-Long,Cho, Chi-Hin,To, Kenneth K.W.. "Reversal of P-gp and BCRP-mediated MDR by tariquidar derivatives". . p. 560 - 572. Retrieved 2015/07/28.