Desferal

デスフェラール

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/12/06 16:26:42」(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[citation needed]
Other names N'-[5-(Acetyl-hydroxy-amino)pentyl]-N-[5-[3-(5-aminopentyl-hydroxy-carbamoyl) propanoylamino]pentyl]-N-hydroxy-butane diamide[citation needed]
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). 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 although it 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.

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

• The anti-cancer activity of dihydroartemisinin is associated with induction of iron-dependent endoplasmic reticulum stress in colorectal carcinoma HCT116 cells.

• Lu JJ, Chen SM, Zhang XW, Ding J, Meng LH.SourceDivision of Anti-tumor Pharmacology, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 201203, People's Republic of China.
• Investigational new drugs.Invest New Drugs.2011 Dec;29(6):1276-83. Epub 2010 Jul 7.
• Dihydroartemisinin (DHA), the main active metabolite of artemisinin derivatives, is among the artemisinin derivatives possessing potent anti-malarial and anti-cancer activities. In the present study, we found that DHA displayed significant anti-proliferative activity in human colorectal carcinoma HC
• PMID 20607588

• Iron-mediated lipid peroxidation and lipid raft disruption in low-dose silica-induced macrophage cytokine production.

• Premasekharan G, Nguyen K, Contreras J, Ramon V, Leppert VJ, Forman HJ.SourceSchool of Engineering, University of California at Merced, Merced, CA 95343, USA.
• Free radical biology & medicine.Free Radic Biol Med.2011 Sep 15;51(6):1184-94. Epub 2011 Jun 23.
• Silica inhalation can induce respiratory disease. Iron is suspected of playing an important role in silica-mediated respiratory toxicity, but unambiguously determining its role has been hampered by incomplete characterization, use of high particle doses, and lack of understanding of proinflammatory
• PMID 21741475

Japanese Journal

• 鉄を視点とするアスベスト発がんの解明と予防·診断·治療への応用の可能性

• 豊國 伸哉
• 肺癌 49(4), 362-367, 2009
• 目的．アスベストの発がん機構を解明する．方法．アスベスト（UICC: クリソタイル，クロシドライト，アモサイト）の物理化学的な性質を再検討する一方，培養細胞や実験動物個体にアスベストの投与を行い，生物学的性質を詳細に評価した．結果．ラジカル発生の触媒能はアモサイト＞クロシドライト＞＞＞クリソタイルであり，それは種々のキレート剤の存在で修飾を受けた．貪食細胞以外に，中皮細胞や腺癌細胞もアスベスト繊維 …
• NAID 130000122998

• A Comparison between the Acid-Catalysed Reactions of Some Dihydroxamic Acids, Monohydroxamic Acids and Desferal

• GHOSH Kallol K.,PATLE Shyam Kumar,SHARMA Pokhraj,RAJPUT Surendra Kumar
• Bulletin of the Chemical Society of Japan 76(2), 283-290, 2003-02-15
• NAID 10010538404

Related Links

• Desferal (Deferoxamine) Drug Information: User Reviews, Side ...

Learn about the prescription medication Desferal (Deferoxamine), drug uses, dosage, side effects, drug interactions, warnings, reviews and patient labeling.

Related Pictures

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★リンクテーブル★

リンク元	「デフェロキサミン」「deferoxamine mesilate」「desferrioxamine」
関連記事	「desferal」

「デフェロキサミン」

　　[★]

英

deferoxamine

化

メシル酸デフェロキサミン deferoxamine mesilate

商

デスフェラール Desferal

関

デスフェリオキサミン、デスフェラール

• キレート剤
• CAS:138-14-7
• C₂₅H₄₈N₆O₈･CH₄SO₃

http://www.genome.jp/kegg-bin/get_entry?dr+D01186

適応

• 鉄中毒

「deferoxamine mesilate」

　　[★] デフェロキサミン 。メシル酸デフェロキサミン

関

deferoxamine、Desferal、desferrioxamine

「desferrioxamine」

　　[★]

デスフェリオキサミン

関

deferoxamine、deferoxamine mesilate、Desferal

「desferal」

　　[★]

同

Desferal

関

Deferoxamine mesylate