Deferoxamine

Deferoxamine
Skeletal formula and spacefill model of deferoxamine
Clinical data
Trade namesDesferal
Other namesdesferrioxamine B, desferoxamine B, DFO-B, DFB ,N'-[5-(Acetyl-hydroxy-amino)pentyl]-N-[5-[3-(5-aminopentyl-hydroxy-carbamoyl) propanoylamino]pentyl]-N-hydroxy-butane diamide
AHFS/Drugs.comMonograph
Routes of
administration
  • intramuscular
  • intravenous
  • subcutaneous
ATC code
Pharmacokinetic data
Elimination half-life6 hours
Identifiers
  • N'-{5-[Acetyl(hydroxy)amino]pentyl}-N-[5-({4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanoyl}amino)pentyl]-N-hydroxysuccinamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.671 Edit this at Wikidata
Chemical and physical data
FormulaC25H48N6O8
Molar mass560.693 g·mol−1
3D model (JSmol)
  • CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
  • 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)
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  • Key:UBQYURCVBFRUQT-UHFFFAOYSA-N

Deferoxamine (DFOA), also known as desferrioxamine and sold under the brand name Desferal, is a medication that binds iron and aluminium.[1] It is specifically used in iron overdose, hemochromatosis either due to multiple blood transfusions or an underlying genetic condition, and aluminium toxicity in people on dialysis.[1][2] It is used by injection into a muscle, vein, or under the skin.[1]

Common side effects include pain at the site of injection, diarrhea, vomiting, fever, hearing loss, and eye problems.[1] Severe allergic reactions including anaphylaxis and low blood pressure may occur.[1] It is unclear if use during pregnancy or breastfeeding is safe for the baby.[3] Deferoxamine is a siderophore from the bacteria Streptomyces pilosus.[4][5]

Deferoxamine was approved for medical use in the United States in 1968.[1] It is on the World Health Organization's List of Essential Medicines.[6]

  1. ^ a b c d e f "Deferoxamine Mesylate". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  2. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 61–62. hdl:10665/44053. ISBN 9789241547659.
  3. ^ "Deferoxamine (Desferal) Use During Pregnancy". www.drugs.com. Archived from the original on 21 December 2016. Retrieved 13 December 2016.
  4. ^ Giardina PJ, Rivella S (2012). "Thalassemia Syndromes". In Hoffman R, Benz Jr EJ, Silberstein LE, Heslop H, Weitz J, Anastasi J (eds.). Hematology: Diagnosis and Treatment (6th ed.). Elsevier Health Sciences. p. 515. ISBN 978-1-4557-4041-3. Archived from the original on 2016-12-20.
  5. ^ Keberle H (October 1964). "The Biochemistry of Desferrioxamine and its Relation to Iron Metabolism". Annals of the New York Academy of Sciences. 119 (2): 758–768. doi:10.1111/j.1749-6632.1965.tb54077.x. PMID 14219455. S2CID 37277528.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.