Deferiprone

Base Information

• Chemical Name: Deferiprone
• CAS No.: 30652-11-0
• Molecular Formula: C7H9NO2
• Molecular Weight: 139.154
• Hs Code.: 29333990
• European Community (EC) Number: 629-275-0
• NSC Number: 758880
• UNII: 2BTY8KH53L
• DSSTox Substance ID: DTXSID6040666
• Nikkaji Number: J134.056E
• Wikipedia: Deferiprone
• Wikidata: Q749664
• NCI Thesaurus Code: C73030
• RXCUI: 11645
• Metabolomics Workbench ID: 65083
• ChEMBL ID: CHEMBL70927
• Mol file: 30652-11-0.mol

Synonyms:1,2 Dimethyl 3 hydroxy 4 pyridinone;1,2 Dimethyl 3 hydroxypyrid 4 one;1,2 Dimethyl 3 hydroxypyridin 4 one;1,2-dimethyl-3-hydroxy-4-pyridinone;1,2-dimethyl-3-hydroxypyrid-4-one;1,2-dimethyl-3-hydroxypyridin-4-one;3 Hydroxy 1,2 dimethyl 4 pyridinone;3-hydroxy-1,2-dimethyl-4-pyridinone;deferiprone;DMOHPO;Ferriprox;HDMPP

Chemical Property of Deferiprone

Chemical Property:

• Appearance/Colour: White needles
• Vapor Pressure: 0.0107mmHg at 25°C
• Melting Point: 272-275 °C(lit.)
• Refractive Index: 1.564
• Boiling Point: 232.7 °C at 760 mmHg
• PKA: pKa1 3.3, pKa2 9.7(at 25℃)
• Flash Point: 94.5 °C
• PSA: 42.23000
• Density: 1.225 g/cm³
• LogP: 0.39930
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in Water (up to 5 mg/ml with warming).
• Water Solubility.: Soluble in hot water
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 139.063328530
• Heavy Atom Count: 10
• Complexity: 228

Purity/Quality:

Deferiprone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Hematological Agents
• Canonical SMILES: CC1=C(C(=O)C=CN1C)O
• Recent ClinicalTrials: Effect of Tafoxiparin on Cervical Ripening and Induction of Labor in Term Pregnant Women With an Unripe Cervix
• Recent EU Clinical Trials: Safety and acceptability of deferiprone delayed release tablets in patients with systemic iron overload
• Recent NIPH Clinical Trials: Evaluation of iron chelator administration, and cochlear implantation for superficial siderosis
• Description: Deferiprone, the first oral iron chelator, was marketed in India for the management of thalassaemia. Patients with thalassaemia, a blood related genetic disorder, require life time transfusion which causes excessive deposition of iron in liver and spleen, subsequent damage to organs and eventually death unless iron is removed by a chelator. Deferiprone is a potent iron chelator that mobilizes excessive iron from iron storage proteins ferritin and hemosiderin, from iron saturated transferrin and lactoferrin, but not from hemoglobin. The deferiprone-iron complex is excreted in urine and bile. Deferiprone was reportedly well accepted by patients and no hematological toxicity was observed. Deferiprone has also been demonstrated as an effective and safe chelator in the mobilization of aluminum.
• Uses: 3-Hydroxy-1,2-dimethyl-4(1H)-pyridone (OH-pyridone) may be used in the bacterial killing assays. It has been employed as hydroxyketone chelating agent and its cytotoxic action against oral human normal and tumor cell lines has been evaluated. iron chelating agent A chelator that could replace disferrioxamine. It is orally and parenterally effective in the removal of iron in vivo from rabbits and mice and also from transferrin and ferritin in vitro
• Clinical Use: Orally administered chelator:Treatment of transfusional iron overload
• Drug interactions: Potentially hazardous interactions with other drugsNone known.

Technology Process of Deferiprone

There total 15 articles about Deferiprone 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: 80.0%

1,2-dimethyl-3-(benzyloxy)-4(1H)-pyridinone (90037-22-2) → deferiprone (30652-11-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h;

DOI:10.1021/jo960854v

Reference yield: 69.0%

Maltol (118-71-8) + methylamine (74-89-5) → deferiprone (30652-11-0)

Guidance literature:

In water; for 10h; Reflux;

DOI:10.1021/acs.jafc.9b06296

Reference yield: 69.0%

→ deferiprone (30652-11-0)

Guidance literature:

With ammonia; In water; for 10h; Reflux;

upstream raw materials:

Maltol

methylamine

3-Hydroxy-1,2-dimethyl-1H-pyridin-4-one; compound with acetic acid

1,2-dimethyl-3-(benzyloxy)-4(1H)-pyridinone

Downstream raw materials:

3-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyloxy)-1,2-dimethyl-4(1H)-pyridinone

1,2-dimethyl-3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)pyridin-4(1H)-one

1,2-dimethyl-4-oxo-1,4-dihydropyridin-3-yl 4-nitrobenzenesulfonate

1,2-dimethyl-4-oxo-1,4-dihydropyridin-3-yl 4-methylbenzenesulfonate

Refernces

• 1、 Chan,Venkataram,Grant,Rahman. "Solid state properties of an oral iron chelator, 1,2-dimethyl-3-hydroxy-4-pyridone, and its acetic acid solvate. I: Physicochemical characterization, intrinsic dissolution rate, and solution thermodynamics". . p. 677 - 685. Retrieved 1991.
• 2、 Gajic, Natalie,Harringer, Sophia,Hejl, Michaela,Jakupec, Michael A.,Kandioller, Wolfgang,Keppler, Bernhard K.,Matzinger, Manuel. "First insights into the novel class of organometallic compounds bearing a bidentate selenopyridone coordination motif: Synthesis, characterization, stability and biological investigations". . . Retrieved 2020.
• 3、 Yu, Xiuqiang,Zhu, Xinyue,Zhou, Yang,Li, Qinglin,Hu, Zhan,Li, Ting,Tao, Jun,Dou, Menglan,Zhang, Meng,Shao, Yu,Sun, Ranfeng. "Discovery of N-Aryl-pyridine-4-ones as Novel Potential Agrochemical Fungicides and Bactericides". . p. 13904 - 13913. Retrieved 2019/12/24.