N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide

• ChemBase编号: 626
• 分子式: C25H48N6O8
• 平均质量: 560.68402
• 单一同位素质量: 560.35336253
• SMILES: ON(CCCCCNC(=O)CCC(=O)N(O)CCCCCN)C(=O)CCC(=O)NCCCCCN(O)C(=O)C
• Canonical SMILES: NCCCCCN(C(=O)CCC(=O)NCCCCCN(C(=O)CCC(=O)NCCCCCN(C(=O)C)O)O)O
• 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)
• InChIKey: UBQYURCVBFRUQT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide
• IUPAC传统名: deferoxamine
• 商标名: Desferal; Desferan; Desferex; Desferin; Desferral; Desferrin
• 别名: Deferoxamine mesylate; Deferoxaminum; Deferrioxamine; Deferoxamin; DFO; N-Benzoylferrioxamine B; DF B; DFOA; DFOM; Desferrioxamine; Desferrioxamine B; Deferrioxamine B; Deferoxamide B; Deferoxamine B; Deferoxamine; N'-[5-(Acetyl-hydroxy-amino)pentyl]-N-[5-[3-(5-aminopentyl-hydroxy-carbamoyl) propanoylamino]pentyl]-N-hydroxy-butane diamide

登记号

• CAS号: 70-51-9
• Beilstein号: 2514118
• PubChem SID: 160964089; 46506395
• PubChem CID: 2973
• CHEBI ID: 4356
• ATC码: V03AC01
• CHEMBL: 556
• Chemspider ID: 2867
• DrugBank ID: DB00746
• KEGG ID: D03670
• 美国药典/FDA物质标识码: J06Y7MXW4D
• 维基百科标题: Deferoxamine

理论计算性质

JChem

• Acid pKa: 7.915494
• 质子受体: 9
• 质子供体: 6
• LogD (pH = 5.5): -4.9015827
• LogD (pH = 7.4): -3.638875
• Log P: -3.365162
• 摩尔折射率: 144.9508 cm^3
• 极化性: 56.376564 Å^3
• 极化表面积: 205.84 Å^2
• 可自由旋转的化学键: 23
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 0.93
• LOG S: -3.75
• 溶解度: 9.90e-02 g/l

分子性质

理化性质

• 溶解度: 1.2 mg/mL (at 20°C, 1.2%)
• 分配系数: -0.614
• 疏水性(logP): -2.2
• pKa: 9.079
• pKb: 4.918

药理学性质

• 给药途径: Intramuscular; Intraperitoneal; Intravenous; Oral; Subcutaneous
• 半衰期: 6 hours

详细说明

DrugBank - DB00746

• Drug Groups: approved
• Description: Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form. [PubChem]
• Indication: Used to treat acute iron or aluminum toxicity (an excess of aluminum in the body) in certain patients. Also used in certain patients with anemia who must receive many blood transfusions.
• Pharmacology: Deferoxamine, otherwise known as desferrioxamine or desferal, is a chelating agent used to remove excess iron or aluminum from the body. It acts by binding free iron or aluminum in the bloodstream and enhancing its elimination in the urine. By removing excess iron or aluminum, the agent reduces the damage done to various organs and tissues, such as the liver.
• Toxicity: Intravenous LD₅₀ in mouse, rat, and rabbit is 340 mg/kg, 520 mg/kg, and 600 mg/kg, respectively. Subcutaneous LD₅₀ in mouse and rat is 1600 mg/kg and >1000 mg/kg, respectively. Oral LD₅₀ in mouse and rat is >3000 mg/kg and >1000 mg/kg, respectively. Nephrotoxicity, ototoxicity and retinal toxicity have been reported following long-term administration for chronic iron overload.
• Affected Organisms: Humans and other mammals
• Biotransformation: Deferoxamine is mainly metabolised in the plasma and hepatic metabolism is minimal. A number of metabolites have been isolated but not characterised. Some metabolites of deferoxamine, most notably the product of oxidative deamination, also chelate iron, and thus the antidotal effect of the drug appears unaffected by hepatic metabolism.
• Absorption: Deferoxamine is rapidly absorbed after intramuscular or subcutaneous administration, but only poorly absorbed from the gastrointestinal tract in the presence of intact mucosa.
• Half Life: Biphasic elimination pattern in healthy volunteers with a first rapid phase half life of 1 hour and a second slow phase half-life of 6 hours.
• Protein Binding: Less than 10% bound to serum proteins in vitro.
• Elimination: Deferoxamine mesylate is metabolized principally by plasma enzymes, but the pathways have not yet been defined. Some is also excreted in the feces via the bile.
• References: [Link]
• External Links: Wikipedia; Drugs.com

参考文献

• Link