Deferoxamine
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Skeletal formula and spacefill model of deferoxamine
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| Clinical data | |
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| Trade names | Desferal |
| AHFS/Drugs.com | Monograph |
| Pregnancy category |
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| ATC code | V03AC01 (WHO) |
| Pharmacokinetic data | |
| Biological half-life | 6 hours |
| Identifiers | |
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| Synonyms | desferrioxamine 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 |
| CAS Number | 70-51-9  |
| PubChem (CID) | 2973 |
| DrugBank | DB00746 |
| ChemSpider | 2867 |
| UNII | J06Y7MXW4D |
| KEGG | D03670 |
| ChEBI | CHEBI:4356 |
| ChEMBL | CHEMBL556 |
| ECHA InfoCard | 100.000.671 |
| Chemical and physical data | |
| Formula | C25H48N6O8 |
| Molar mass | 560.69 g·mol−1 |
| 3D model (Jmol) | Interactive image |
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Deferoxamine (DFOA), 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 it of injection, diarrhea, vomiting, fever, hearing loss, and eye problems. 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]
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, the most important medications needed in a basic health system.[5] The wholesale cost in the developing world is about 6.76 to 13.52 USD per dose.[6] In the United States a course of treatment costs more than 200 USD.[7]
Medical uses[edit]
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.[8]
Mechanism[edit]
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).[citation needed] Deferoxamine may modulate expression[9] and release of inflammatory mediators by specific cell types.[10]
Research[edit]
Deferoxamine is being studied as a treatment for spinal cord injury[11] and intracerebral hemorrhage.[12]
See also[edit]
References[edit]
- ^ a b c d e "Deferoxamine Mesylate". The American Society of Health-System Pharmacists. Retrieved 8 December 2016.
- ^ WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. 61-62. ISBN 9789241547659. Retrieved 8 December 2016.
- ^ "Deferoxamine (Desferal) Use During Pregnancy". www.drugs.com. Retrieved 13 December 2016.
- ^ Hoffman, Ronald; Jr, Edward J. Benz; Silberstein, Leslie E.; Heslop, Helen; Weitz, Jeffrey; Anastasi, John (2012). Hematology: Diagnosis and Treatment (6 ed.). Elsevier Health Sciences. p. 515. ISBN 1455740411.
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ "Deferoxamine". International Drug Price Indicator Guide. Retrieved 8 December 2016.
- ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 470. ISBN 9781284057560.
- ^ 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
- ^ 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
- ^ 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
- ^ http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/orphans/2009/11/human_orphan_000120.jsp&mid=WC0b01ac058001d12b
- ^ Wu H, Wu T, Xu X, Wang J, Wang J (May 2011). "Iron toxicity in mice with collagenase-induced intracerebral hemorrhage". J Cereb Blood Flow Metab. 31 (5): 1243–50. doi:10.1038/jcbfm.2010.209. PMC 3099628
. PMID 21102602.
