|Accession Number||DB00746 (APRD00904)|
Natural product isolated from Streptomyces pilosus. It forms iron complexes and is used as a chelating agent, particularly in the mesylate form. [PubChem]
|External IDs||Ba 29837 / Ba 33112|
|Approved Prescription Products|
|Approved Generic Prescription Products|
|Approved Over the Counter Products||Not Available|
|Unapproved/Other Products||Not Available|
|Brand mixtures||Not Available|
|Weight||Average: 560.684 |
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.
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.
|Mechanism of action|
Deferoxamine works in treating iron toxicity by binding trivalent (ferric) iron (for which it has a strong affinity), forming ferrioxamine, a stable complex which is eliminated via the kidneys. 100 mg of deferoxamine is capable of binding approximately 8.5 mg of trivalent (ferric) iron. Deferoxamine works in treating aluminum toxicity by binding to tissue-bound aluminum to form aluminoxamine, a stable, water-soluble complex. The formation of aluminoxamine increases blood concentrations of aluminum, resulting in an increased concentration gradient between the blood and dialysate, boosting the removal of aluminum during dialysis. 100 mg of deferoxamine is capable of binding approximately 4.1 mg of aluminum.
Deferoxamine is rapidly absorbed after intramuscular or subcutaneous administration, but only poorly absorbed from the gastrointestinal tract in the presence of intact mucosa.
|Volume of distribution||Not Available|
Less than 10% bound to serum proteins in vitro.
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.
|Route of 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.
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.
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.
|Pharmacogenomic Effects/ADRs||Not Available|
|Food Interactions||Not Available|
Zoltan Konyari, Vilmos Keri, Antal Kovacs, Sandor Horkay, Laszlo Eszenyi, Janos Erdelyi, Ilona Himesi, Gyorgy Toth, Janos Balint, SzilaJudit, Ferenc Vinczi, Csaba Szabo, Nelli Sas, "Process for the preparation of high-purity deferoxamine salts." U.S. Patent US5374771, issued July, 1965.US5374771
|PDB Entries||Not Available|
|FDA label||Not Available|
|MSDS||Download (52.1 KB)|
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|Predicted ADMET features|
|Mass Spec (NIST)||Not Available|
|Description||This compound belongs to the class of chemical entities known as acetohydroxamic acids. These are organic compounds that contain a hydroxamic acid group carrying a methyl group attached to its carbon center.|
|Super Class||Organic compounds|
|Class||Organic acids and derivatives|
|Sub Class||Carboxylic acids and derivatives|
|Direct Parent||Acetohydroxamic acids|
|Alternative Parents||Acetamides / Amino acids and derivatives / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds|
|Substituents||Acetamide / Acetohydroxamic acid / Amino acid or derivatives / Carboximidic acid / Carboximidic acid derivative / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound / Carbonyl group / Organic nitrogen compound / Primary amine|
|Molecular Framework||Aliphatic acyclic compounds|
|External Descriptors||acyclic desferrioxamine (CHEBI:4356 ) / a hydroxamate siderophore (CPD-3764 )|
- Small molecule
- Pharmacological action
- Elihu N, Anandasbapathy S, Frishman WH: Chelation therapy in cardiovascular disease: ethylenediaminetetraacetic acid, deferoxamine, and dexrazoxane. J Clin Pharmacol. 1998 Feb;38(2):101-5. [PubMed:9549639 ]
- Hershko C, Link G, Konijn AM, Cabantchik ZI: Objectives and mechanism of iron chelation therapy. Ann N Y Acad Sci. 2005;1054:124-35. [PubMed:16339658 ]
- Cappellini MD, Musallam KM, Taher AT: Overview of iron chelation therapy with desferrioxamine and deferiprone. Hemoglobin. 2009;33 Suppl 1:S58-69. doi: 10.3109/03630260903346924. [PubMed:20001633 ]
- Small molecule
- Pharmacological action
- Kontoghiorghes GJ: Comparative efficacy and toxicity of desferrioxamine, deferiprone and other iron and aluminium chelating drugs. Toxicol Lett. 1995 Oct;80(1-3):1-18. [PubMed:7482575 ]
- Yokel RA: Aluminum chelation: chemistry, clinical, and experimental studies and the search for alternatives to desferrioxamine. J Toxicol Environ Health. 1994 Feb;41(2):131-74. [PubMed:8301696 ]
- Day JP, Ackrill P: The chemistry of desferrioxamine chelation for aluminum overload in renal dialysis patients. Ther Drug Monit. 1993 Dec;15(6):598-601. [PubMed:8122301 ]
- Domingo JL: The use of chelating agents in the treatment of aluminum overload. J Toxicol Clin Toxicol. 1989;27(6):355-67. [PubMed:2697761 ]
- Pharmacological action
- General Function:
- Xanthine oxidase activity
- Specific Function:
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
- Gene Name:
- Uniprot ID:
- Molecular Weight:
- 146422.99 Da
- Rinaldo JE, Gorry M: Protection by deferoxamine from endothelial injury: a possible link with inhibition of intracellular xanthine oxidase. Am J Respir Cell Mol Biol. 1990 Dec;3(6):525-33. [PubMed:2252579 ]