Deferoxamine

Base Information

• Chemical Name: Deferoxamine
• CAS No.: 70-51-9
• Deprecated CAS: 7278-84-4
• Molecular Formula: C25H48 N6 O8
• Molecular Weight: 560.692
• Hs Code.: 2924199090
• European Community (EC) Number: 200-738-5
• NSC Number: 527604
• UNII: J06Y7MXW4D
• DSSTox Substance ID: DTXSID7022887
• Nikkaji Number: J10.199K
• Wikipedia: Deferoxamine
• Wikidata: Q419618
• NCI Thesaurus Code: C416
• RXCUI: 3131
• Metabolomics Workbench ID: 43048
• ChEMBL ID: CHEMBL556
• Mol file: 70-51-9.mol

Synonyms:Deferoxamine;Deferoxamine B;Deferoxamine Mesilate;Deferoxamine Mesylate;Deferoxamine Methanesulfonate;Deferoximine;Deferrioxamine B;Desferal;Desferioximine;Desferrioxamine;Desferrioxamine B;Desferrioxamine B Mesylate;Desferroxamine;Mesilate, Deferoxamine;Mesylate, Deferoxamine;Mesylate, Desferrioxamine B;Methanesulfonate, Deferoxamine

Chemical Property of Deferoxamine

Chemical Property:

• Melting Point: 139°C
• Refractive Index: 1.5540 (estimate)
• Boiling Point: 627.9°C (rough estimate)
• PKA: 9.08±0.50(Predicted)
• PSA: 205.84000
• Density: 1.212g/cm3
• LogP: 2.40420
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 23
• Exact Mass: 560.35336251
• Heavy Atom Count: 39
• Complexity: 739

Purity/Quality:

99.9% ^*data from raw suppliers

DEFEROXAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Hematological Agents
• Canonical SMILES: CC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCNC(=O)CCC(=O)N(CCCCCN)O)O)O
• Recent ClinicalTrials: Iron, Alpha-Synuclein, and Lymphocyte-activation Gene-3 in Ischemic Stroke
• Recent EU Clinical Trials: A Phase I/IIa study to evaluate safety, biodistribution, dosimetry and preliminary diagnostic performance of [68Ga]Ga-Deferoxamine for PET imaging in patients with bacterial infections
• Recent NIPH Clinical Trials: DFO for advanced HCC with impaired liver function
• Description: Deferoxamine was introduced in the 1960s for chelation of iron. It is synthesized by removing a central iron molecule from ferrioxamine B, a compound obtained from the microorganism Streptomyces pilosus. Deferoxamine binds to iron from ferritin and forms ferrioxamine, a very stable and water-soluble chelate with a characteristic reddish color.
• Uses: Chelating agent (iron). Deferoxamine is used for the treatment of both acute iron intoxication and chronic iron overload due to transfusiondependent anemias. It has also been used in trials for malaria treatment and for aluminum chelation in hemodialysis patients. Studies of a rat model of intracerebral hemorrhage have noted that deferoxamine treatment reduced oxidative stress from iron release, indicating a possible role in preventing damage associated with hemorrhagic strokes.

Technology Process of Deferoxamine

There total 28 articles about Deferoxamine 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: 50.0%

C46H64N8O8 → deferoxamine (70-51-9)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 25 ℃; for 0.333333h; under 760.051 Torr;

DOI:10.1002/ejoc.202000439

Reference yield:

N'-<5-<<4-<<5-pentyl>amino>-1,4-dioxobutyl>(phenylmethoxy)amino>pentyl>-N-(4-cyanobutyl)-N-(phenylmethoxy)butanediamide (112139-65-8) → deferoxamine (70-51-9)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jm00115a006

Reference yield:

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine (129245-21-2) → deferoxamine (70-51-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C

2: 87 percent / trifluoroacetic acid (TFA) / CH₂Cl₂ / 0.75 h / 0 - 20 °C

3: 96 percent / pyridine

4: 95 percent / diphenyl phosphorazidate, triethylamine / dimethylformamide / 17 h / 0 - 20 °C

5: 100 percent / trifluoroacetic acid (TFA) / CH₂Cl₂

6: 91 percent / pyridine / 12 h

7: H₂, HCl / 10percent Pd/C / methanol

With pyridine; hydrogenchloride; diphenyl phosphoryl azide; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00115a006

upstream raw materials:

1-Carbobenzoxyamino-6,17-dihydroxy-7,10,18,21-tetraoxy-27-(N-acetyl-hydroxyamino)-6,11,17,22-tetraaza-hepteikosan

N'-<5-<<4-<<5-pentyl>amino>-1,4-dioxobutyl>(phenylmethoxy)amino>pentyl>-N-(4-cyanobutyl)-N-(phenylmethoxy)butanediamide

O-benzyl-N-(5-aminopentyl)-N-(tert-butoxycarbonyl)hydroxylamine

5,16-bis(benzyloxy)-20-cyano-4,12,15-trioxo-5,11,16-triazaeicosanoic acid

Downstream raw materials:

Acetic acid 2-acetoxy-6-(3-{5-[(3-{5-[acetyl-(2,3-diacetoxy-benzoyloxy)-amino]-pentylcarbamoyl}-propionyl)-(2,3-diacetoxy-benzoyloxy)-amino]-pentylcarbamoyl}-propionyl)-[5-(2,3-diacetoxy-benzoylamino)-pentyl]-aminooxycarbonyl)-phenyl ester

N-(2,3-dimethoxy-4-carboxybenzoyl)desferrioxamine B

C₂₅H₄₅GaN₆O₈

deferoxamine iron(III) complex

Refernces

• 1、 Richardson-Sanchez, Tomas,Codd, Rachel. "Engineering a cleavable disulfide bond into a natural product siderophore using precursor-directed biosynthesis". . p. 9813 - 9816. Retrieved 2018/09/10.
• 2、 -. "Polymers with structure-defined functions". . . Retrieved 2011/06/23.