Deferasirox

Base Information

• Chemical Name: Deferasirox
• CAS No.: 201530-41-8
• Molecular Formula: C21H15N3O4
• Molecular Weight: 373.368
• Hs Code.: 2933997500
• European Community (EC) Number: 685-491-5
• UNII: V8G4MOF2V9
• DSSTox Substance ID: DTXSID1048596
• Nikkaji Number: J1.213.542D
• Wikipedia: Deferasirox
• Wikidata: Q5251502
• NCI Thesaurus Code: C48384
• RXCUI: 614373
• Metabolomics Workbench ID: 57161
• ChEMBL ID: CHEMBL550348
• Mol file: 201530-41-8.mol

Synonyms:4-(3,5-bis-(2-hydroxyphenyl)-(1,2,4)-triazol-1-yl)benzoic acid;deferasirox;Exjade;ICL 670;ICL 670A;ICL-670;ICL-670A;ICL670;ICL670A

Chemical Property of Deferasirox

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 260-2620C
• Refractive Index: 1.699
• Boiling Point: 672.123 °C at 760 mmHg
• PKA: pKa1 4.57, pKa2 8.71, pKa3 10.56 (Nick); Also reported in H2O/DM
• Flash Point: 360.287 °C
• PSA: 107.95000
• Density: 1.405 g/cm³
• LogP: 1.08550
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in DMSO (10 mg/ml)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 373.10625597
• Heavy Atom Count: 28
• Complexity: 540

Purity/Quality:

98.5%min , ^*data from raw suppliers

Deferasirox-d8 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Hematological Agents
• Canonical SMILES: C1=CC=C(C(=C1)C2=NN(C(=N2)C3=CC=CC=C3O)C4=CC=C(C=C4)C(=O)O)O
• Recent ClinicalTrials: Low Dose Iron Chelation as TReatment of Oxidative Damage in Sickle Cell Disease
• Recent EU Clinical Trials: Low dose iron chelation as TReatment of Oxidative stress in Sickle cell disease; TROS study
• Recent NIPH Clinical Trials: Deferasirox for patients with advanced hepatocellular carcinoma : pilot study
• Uses: 1. DFS can be used to treat the reversible renal insufficiency caused by Fanconi syndrome. 2. It can be used for the treatment of secondary hemochromatosis. 3. It can be used for the treatment of delayed skin porphyria. 4. It can be used for the treatment of myelodysplastic syndromes. 5. It can be used for the treatment of iron overloading caused by blood transfusion for patients (older than 2 years old) of chronic anemia This information is compiled and edited by Ding Hong of lookchem. (2015-09-18) Orally active tridentate iron chelator Biological Activity Chemical Information Tech Support & FAQs Biological Activity Deferasirox(Exjade) is a rationally-designed oral iron chelator. Its main use is to reduce chronic iron overload in patients who are receiving long-term blood transfusions A tridentate chelator that binds iron with high affinity Labeled Deferasirox, intended for use as an internal standard for the quantification of Deferasirox by GC- or LC-mass spectrometry.
• Description: Linagliptin was originally discovered at Boehringer Ingelheim as an orally active dipeptidyl peptidase-IV (DPP-4) inhibitor. Eli Lilly and Boehringer Ingelheim co-developed and launched linagliptin for type II diabetes as an adjunct to diet and exercise for the improvement of adult glycemic control. Linagliptin has a superior DPP-4 IC50 value of 1 nM, compared with 19 nM for sitagliptin, 24 nM for alogliptin, 50 nM for saxagliptin and 62 nM for vildagliptin. In addition, linagliptin exhibited prolonged pharmacodynamic activity with long-lasting DPP-4 inhibition in several preclinical species. Linagliptin showed good efficacy in phase II clinical trials with doses as low as 5 mg and no signs of hypoglycemia with doses as high as 600 mg. The prolonged pharmacological effect of DPP-4 activity and the good safety/tolerability profile provided the basis for linagliptin’s approval.
• Clinical Use: Treatment of iron overload
• Drug interactions: Potentially hazardous interactions with other drugsAluminium-containing antacids: avoid concomitant use.Aminophylline and theophylline: concentration of aminophylline and theophylline increased, consider reducing aminophylline and theophylline dose.Other nephrotoxic agents: avoid concomitant therapy

Technology Process of Deferasirox

There total 31 articles about Deferasirox 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: 99.0%

4-Hydrazinobenzoic acid (619-67-0) + 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one (1218-69-5) → deferasirox (201530-41-8)

Guidance literature:

With triethylamine; In ethanol; for 2h; Reflux;

Reference yield: 93.0%

4-Hydrazinobenzoic acid (619-67-0) + salicylamide (65-45-2) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → deferasirox (201530-41-8)

Guidance literature:

salicylamide; salicylic acid; With pyridine; thionyl chloride; In toluene; at 120 ℃; for 3h;

4-Hydrazinobenzoic acid;

DOI:10.1021/jacs.0c11641

Reference yield: 85.0%

C20H26N2O5SSi2 (1311284-26-0) + 4-ethoxycarbonylphenylhydrazine (14685-90-6) → deferasirox (201530-41-8)

Guidance literature:

C₂₀H₂₆N₂O₅SSi₂; 4-ethoxycarbonylphenylhydrazine; In ethanol; at 20 ℃;

With hydrogenchloride; In ethanol; water;

upstream raw materials:

4-Hydrazinobenzoic acid

2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one

salicylamide

salicylic acid

Downstream raw materials:

(4-(3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl)phenyl)(4-methylpiperazin-1-yl)methanone

deferasirox methylamine salt

deferasirox n-butylamine salt

deferasirox isopropylamine salt

Refernces

• 1、 Salehi, Samie,Saljooghi, Amir Sh.,Shiri, Ali. "Synthesis, characterization and in vitro anticancer evaluations of two novel derivatives of deferasirox iron chelator". . p. 209 - 217. Retrieved 2016.
• 2、 Taghavi, Faezeh,Saljooghi, Amir Sh.,Gholizadeh, Mostafa,Ramezani, Mohammad. "Deferasirox-coated iron oxide nanoparticles as a potential cytotoxic agent". . p. 2290 - 2298. Retrieved 2016.
• 3、 Han, Hai-Hao,He, Xiao-Peng,Huang, Dan-Ying,Li, Jia,Sedgwick, Adam C.,Sen, Sajal,Sessler, Jonathan L.,Steinbrueck, Axel,Zang, Yi,Zhao, Michael Y.. "In vitrostudies of deferasirox derivatives as potential organelle-targeting traceable anti-cancer therapeutics". supporting information. p. 5678 - 5681. Retrieved 2021/06/16.
• 4、 Wu, Hongfeng,An, Qi,He, Chaoyin,Fan, Xiaodong,Guo, Weihao,Zuo, Minghui,Xu, Chunzhao,Guo, Rui,Chu, Wenyi,Sun, Zhizhong. "Synthesis of 2-(2-Hydroxyaryl)-4H-benzo[e][1,3]oxazin-4-ones by Palladium-Catalyzed C(sp2)?H Hydroxylation via Electro-chemical Oxidation". supporting information. p. 2459 - 2465. Retrieved 2020/04/29.