deferoxamine mesylate

デフェロキサミン deferoxamine、メシル酸デフェロキサミン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/09/29 18:02:30」(JST)

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Deferoxamine
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
PubChem	2973
ChemSpider	2867 Y
UNII	J06Y7MXW4D Y
DrugBank	DB00746
KEGG	D03670 Y
ChEBI	CHEBI:4356 Y
ChEMBL	CHEMBL556 Y
ATC code	V03AC01
Beilstein Reference	2514118
Jmol-3D images	Image 1 Image 2
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
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
Properties
Molecular formula	C25H48N6O8
Molar mass	560.68 g mol−1
log P	−0.614
Acidity (pKa)	9.079
Basicity (pKb)	4.918
Pharmacology
Routes of administration	Intramuscular Intraperitoneal Intravenous Oral Subcutaneous
Elimination half-life	6 hours
Related compounds
Related alkanamides	Stearamidopropyl dimethylamine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.

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).^{[citation needed]} Deferoxamine may modulate expression and release of inflammatory mediators by specific cell types.

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".

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

Deferoxamine has also been used in the treatment of a patient with aceruloplasminemia.

Uses under investigation

A study published in January 2008 suggests that deferoxamine can be used to speed fracture healing. Reducing iron accumulation by deferoxamine has been shown to reduce neuronal death and modestly improve functional outcome after intracerebral hemorrhage in mice. A German company, Spinal Cord Therapeutics GmbH (formerly known as Neuraxo), is developing deferoxamine as a treatment for spinal cord injury under the brand name, Cordaneurin.

See also

• Chelation therapy

References

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

UpToDate Contents

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• 1. サラセミアおよびその他の鉄過剰状態に対するキレート療法 chelation therapy for thalassemia and other iron overload states
• 2. 急性鉄中毒 acute iron poisoning
• 3. 慢性腎臓病におけるアルミニウム毒性 aluminum toxicity in chronic kidney disease
• 4. 鎌状赤血球症における赤血球輸血 red blood cell transfusion in sickle cell disease
• 5. ムコール症（接合真菌症） mucormycosis zygomycosis

English Journal

• Composite chitosan/alginate hydrogel for controlled release of deferoxamine: A system to potentially treat iron dysregulation diseases.

• Rassu G1, Salis A1, Porcu EP2, Giunchedi P1, Roldo M3, Gavini E4.
• Carbohydrate polymers.Carbohydr Polym.2016 Jan 20;136:1338-47. doi: 10.1016/j.carbpol.2015.10.048. Epub 2015 Oct 23.
• Recently, the potential application of deferoxamine (DFO) in several iron dysregulation diseases has been highlighted. However, DFO presents significant limitations in clinical use due to its poor absorption in the gut and very short plasma half-life. To overcome these problems, the feasibility of c
• PMID 26572479

• Deferoxamine Attenuated the Upregulation of Lipocalin-2 Induced by Traumatic Brain Injury in Rats.

• Zhao J1, Xi G1, Wu G1, Keep RF1, Hua Y2.
• Acta neurochirurgica. Supplement.Acta Neurochir Suppl.2016;121:291-4. doi: 10.1007/978-3-319-18497-5_50.
• Intracranial hemorrhage is one of the most common consequences of traumatic brain injury (TBI). The release of iron from the breakdown of hemoglobin during intracerebral hematoma resolution results in an increase in perihematomal non-heme iron. Lipocalin 2 (LCN-2) is a siderophore-binding protein th
• PMID 26463963

• Deferoxamine stimulates LDLR expression and LDL uptake in HepG2 cells.

• Guillemot J1, Asselin MC1, Susan-Resiga D1, Essalmani R1, Seidah NG1.
• Molecular nutrition & food research.Mol Nutr Food Res.2015 Nov 18. doi: 10.1002/mnfr.201500467. [Epub ahead of print]
• SCOPE: Iron overload contributes to the pathogenesis of atherosclerosis and iron chelators are beneficial through their antioxidant properties. Hepatic iron loading increases cholesterol synthesis. Whether iron depletion could affect hepatic cholesterol metabolism is unknown.METHODS AND RESULTS: We
• PMID 26577249

Japanese Journal

• 低酸素環境がマウス胚性幹細胞(ES細胞)の生殖細胞分化に及ぼす影響

• 三原 敏敬,林地 のぞみ,寺村 岳士 [他],小野寺 勇太,松岡 俊樹,福田 寛二,細井 美彦
• 近畿大学先端技術総合研究所紀要 (14), 49-57, 2009-03
• … また、通常酸素濃度でHIFを誘導するDeferoxamine mesylate (DFO)を添加し、その結果を比較する事で、HIF遺伝子が生殖細胞分化に与える影響について検討を行った。 …
• NAID 120002188070

• Contribution of the Photo-Fenton Reaction to Hydroxyl Radical Formation Rates in River and Rain Water Samples

• , , , ,
• Analytical Sciences 23(9), 1137-1142, 2007
• … The hydroxyl radical (OH radical) formation rates from the photo-Fenton reaction in river and rain water samples were determined by using deferoxamine mesylate (DFOM), which makes a stable and strong complex with Fe(III), resulting in a suppression of the photo-Fenton reaction. …
• NAID 130004441545

• 多彩な病態を呈した続発性ヘモクロマトーシス　　しん出性紅斑を契機に診断に至った１例

• 山路 雅己,調 裕次,高木 圭一,川津 智是
• 皮膚 40(2), 142-146, 1998
• 74歳女性。約10年間, 鉄剤を内服していた。1ヵ月前から全身に蚤痒性紅斑が多発したため来院した。血小板減少, 肝機能異常, 甲状腺機能低下, 糖尿病, Ca19-9高値などを認め, 血清フェリチン8590ng/ml, UIBC 7μg/dl, MRIにて肝臓に著明な鉄沈着を認めたため続発性ヘモクロマトーシスと診断した。紅斑はステロイドの外用で軽快し, あとにヘモジデリンによる色素沈着を残した。メ …
• NAID 130004045871

Related Links

• Deferoxamine mesylate salt powder, ≥92.5% (TLC) | Sigma-Aldrich

Sigma-Aldrich offers Sigma-Deferoxamine mesylate salt for your research needs. Find product specific information, including CAS, MSDS, protocols and references.

• Deferoxamine - Wikipedia, the free encyclopedia

Deferoxamine. From Wikipedia, the free encyclopedia. Jump to: navigation, search ... iron from the body. The mesylate salt of DFO-B is commercially available. ... Deferoxamine is used to treat acute iron poisoning, especially in small children.

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• メシル酸、メシル酸塩、メシレート

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mesilate、methanesulfonate