Deferoxamine

Deferoxamine

Systematic (IUPAC) name
N'-{5-[acetyl(hydroxy)amino]pentyl}-N-[5-({4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoyl}amino)pentyl]-N-hydroxysuccinamide
Clinical data
Trade names	Desferal
AHFS/Drugs.com	monograph
Pregnancy cat.	?
Legal status	?
Routes	Oral, IV, IM, SQ
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half-life	6 hours
Excretion	?
Identifiers
CAS number	70-51-9 Y
ATC code	V03AC01
PubChem	CID 2973
DrugBank	APRD00904
ChemSpider	2867 Y
UNII	J06Y7MXW4D Y
KEGG	D03670 Y
ChEBI	CHEBI:4356 Y
ChEMBL	CHEMBL556 Y
Synonyms	N'- [5-(acetyl-hydroxy-amino)pentyl]-N-[5-[3-(5-aminopentyl-hydroxy-carbamoyl) propanoylamino]pentyl]-N-hydroxy-butane diamide
Chemical data
Formula	C25H48N6O8
Mol. mass	560.684 g/mol
SMILES	eMolecules & PubChem
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
N(what is this?)  (verify)

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.^[1] The mesylate salt of DFO-B is commercially available.

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. A recent study also shows that it speeds healing of nerve damage (and minimizes the extent of recent nerve trauma). Deferoxamine may modulate expression^[2] and release of inflammatory mediators by specific cell types.^[3]

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 (SQ infusion) 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 rose urine". As an alternative to injections, in 2009 Iranian researchers developed the world's first pill version of deferoxamine;^[4] when used, the pills reportedly avoid the pain commonly experienced after receiving injections of the drug.^[5]

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

A study published in January 2008 suggests that deferoxamine can be used to speed fracture healing.^[6]

Deferoxamine has also been used in the treatment of a patient with aceruloplasminemia.^[7]

See also

• Chelation therapy

References

1. ^ Miller, Marvin J. (1989-11-01). "Syntheses and therapeutic potential of hydroxamic acid based siderophores and analogs". Chemical Reviews 89 (7): 1563–1579. doi:10.1021/cr00097a011. 
2. ^ Lee HJ, Lee J, Lee SK, Lee SK, Kim EC. Differential regulation of iron chelator-induced IL-8 synthesis via MAP kinase and NF-kappaB in immortalized and malignant oral keratinocytes. BMC Cancer. 2007 Sep 13;7:176. PMID: 17850672
3. ^ Choi EY, Kim EC, Oh HM, Kim S, Lee HJ, Cho EY, Yoon KH, Kim EA, Han WC, Choi SC, Hwang JY, Park C, Oh BS, Kim Y, Kimm KC, Park KI, Chung HT, Jun CD. Iron chelator triggers inflammatory signals in human intestinal epithelial cells: involvement of p38 and extracellular signal-regulated kinase signaling pathways. J Immunol. 2004 Jun 1;172(11):7069-77. PMID: 15153529
4. ^ Iran produces first desferal pills
5. ^ Iran Produces First Desferal Pills." Press TV 9 May 2009. 9 May 2009
6. ^ Science Daily Report
7. ^ Miyajima, H.; Takahashi, Y.; Kamata, T.; Shimizu, H.; Sakai, N.; Gitlin, J. D. : Use of desferrioxamine in the treatment of aceruloplasminemia. Ann. Neurol. 41: 404-407, 1997. PMID 9066364

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