Deferoxamine

Deferoxamine

Skeletal formula of deferoxamine
Spacefill model of deferoxamine
Names
IUPAC name N'-{5-[Acetyl(hydroxy)amino]pentyl}-N-[5-({4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoyl}amino)pentyl]-N-hydroxysuccinamide
Other names N'-[5-(Acetyl-hydroxy-amino)pentyl]-N-[5-[3-(5-aminopentyl-hydroxy-carbamoyl) propanoylamino]pentyl]-N-hydroxy-butane diamide
Identifiers
CAS Number	70-51-9 Y
Beilstein Reference	2514118
ChEBI	CHEBI:4356 Y
ChEMBL	ChEMBL556 Y
ChemSpider	2867 Y
DrugBank	DB00746 Y
Jmol 3D model	Interactive image Interactive image
KEGG	D03670 Y
PubChem	2973
UNII	J06Y7MXW4D Y
InChI InChI=1S/C25H48N6O8/c1-21(32)29(37)18-9-3-6-16-27-22(33)12-14-25(36)31(39)20-10-4-7-17-28-23(34)11-13-24(35)30(38)19-8-2-5-15-26/h37-39H,2-20,26H2,1H3,(H,27,33)(H,28,34) Y Key: UBQYURCVBFRUQT-UHFFFAOYSA-N Y
SMILES Cc(:[o]):n(:[oH])CCCCC[nH]:c(:[o])CCc(:[o]):n(:[oH])CCCCC[nH]:c(:[o])CCc(:[o]):n(:[oH])CCCCCN CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
Properties
Chemical formula	C25H48N6O8
Molar mass	560.69 g·mol−1
log P	−0.614
Acidity (pKa)	9.079
Basicity (pKb)	4.918
Pharmacology
ATC code	V03AC01
Routes of administration	Intramuscular Intraperitoneal Intravenous Oral Subcutaneous
Pharmacokinetics:
Biological half-life	6 hours
Related compounds
Related alkanamides	Stearamidopropyl dimethylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Deferoxamine (also known as desferrioxamine B, desferoxamine B, DFO-B, DFOA, DFB or desferal) is a bacterial siderophore produced by the Actinobacteria Streptomyces pilosus. It has medical applications as a chelating agent used to remove excess iron from the body. The mesylate salt of DFO-B is commercially available.

It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.

Medical uses

Deferoxamine is used to treat acute iron poisoning, especially in small children. This agent is also frequently used to treat hemochromatosis, a disease of iron accumulation that can be either genetic or acquired. Acquired hemochromatosis is common in patients with certain types of chronic anemia (e.g. thalassemia and myelodysplastic syndrome) who require many blood transfusions, which can greatly increase the amount of iron in the body. Administration for chronic conditions is generally accomplished by subcutaneous injection over a period of 8–12 hours each day. Administration of deferoxamine after acute intoxication may color the urine a pinkish red, a phenomenon termed "vin rosé urine".

Apart from iron toxicity, deferoxamine can be used to treat aluminium toxicity (an excess of aluminium in the body) in select patients. In US, the drug is not FDA-approved for this use.

Deferoxamine is also used to minimize doxorubicin's cardiotoxic side effects and in the treatment of a patient with aceruloplasminemia.

Mechanism

Deferoxamine acts by binding free iron in the bloodstream and enhancing its elimination in the urine. By removing excess iron, the agent reduces the damage done to various organs and tissues, such as the liver. Also, it speeds healing of nerve damage (and minimizes the extent of recent nerve trauma). Deferoxamine may modulate expression and release of inflammatory mediators by specific cell types.

Research

Deferoxamine is being studied as a treatment for spinal cord injury and intracerebral hemorrhage.

See also

• Chelation therapy

References

• British National Formulary 55, March 2008; ISBN 978 085369 776 3 p. 32