Banner
targets (2) enzymes (1)
for drugs
Identification
Name Deferoxamine
Accession Number DB00746 (APRD00904)
Type small molecule
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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Deferoxamide B
Deferoxamin
Deferoxamine B
Deferoxamine mesylate
Deferoxaminum
Deferrioxamine
Deferrioxamine B
Desferrioxamine
Desferrioxamine B
DF B
DFO
DFOA
DFOM
N-Benzoylferrioxamine B
First Prev Next Last
Salts Not Available
Brand names
Name Company
Desferal
Desferan
Desferex
Desferin
Desferral
Desferrin
Brand mixtures Not Available
Categories
  • Iron Chelating Agents
  • Chelating agent
  • Siderophores
CAS number 70-51-9
Weight Average: 560.684
Monoisotopic: 560.353362542
Chemical Formula C25H48N6O8
InChI Key InChIKey=UBQYURCVBFRUQT-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydroxyacetamido)pentyl]carbamoyl}propanamido)pentyl]butanediamide
SMILES
CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Polypeptides
Substructures
  • Hydroxy Compounds
  • Hydroxamic Acids
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
  • Polypeptides
  • Carboxamides and Derivatives
  • Hydroxylamines and Derivatives
Pharmacology
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.
Pharmacodynamics 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.
Absorption 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
Protein binding Less than 10% bound to serum proteins in vitro.
Metabolism 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.
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.
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Watson laboratories inc
  • Novartis pharmaceuticals corp
Packagers
Dosage forms
Form Route Strength
Powder, for solution Intramuscular
Powder, for solution Intraperitoneal
Powder, for solution Intravenous
Prices
Unit description Cost Unit
Desferal 2 gram vial 113.94 USD vial
Desferal 2 g/vial 60.52 USD vial
Deferoxamine 2 gram vial 46.25 USD vial
Desferrioxamine Mesilate 2 g/vial 33.89 USD vial
Pms-Deferoxamine 2 g/vial 33.89 USD vial
Desferal 500 mg Solution Vial 23.92 USD vial
Desferal 500 mg/vial 15.07 USD vial
Desferrioxamine Mesilate 500 mg/vial 8.44 USD vial
Pms-Deferoxamine 500 mg/vial 8.44 USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 140 °C PhysProp
water solubility 1.2E+004 mg/L (at 20 °C) MERCK INDEX (1996)
logP -2.2 Not Available
Predicted Properties
Property Value Source
water solubility 9.90e-02 g/l ALOGPS
logP 0.93 ALOGPS
logP -3.4 ChemAxon
logS -3.8 ALOGPS
pKa (strongest acidic) 7.92 ChemAxon
pKa (strongest basic) 10.23 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 9 ChemAxon
hydrogen donor count 6 ChemAxon
polar surface area 205.84 ChemAxon
rotatable bond count 23 ChemAxon
refractivity 144.95 ChemAxon
polarizability 62.41 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Link
External Links
Resource Link
KEGG Drug D03670 Link_out
KEGG Compound C06940 Link_out
PubChem Compound 2973 Link_out
PubChem Substance 46506395 Link_out
ChemSpider 2867 Link_out
ChEBI 4356 Link_out
ChEMBL 4356 Link_out
PharmGKB PA164746490 Link_out
Drug Product Database 2243450 Link_out
Drugs.com http://www.drugs.com/cdi/deferoxamine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Deferoxamine Link_out
ATC Codes
  • V03AC01
AHFS Codes
  • 64:00.00
PDB Entries Not Available
FDA label Not Available
MSDS show (52.1 KB)
Interactions
Drug Interactions
Drug Interaction
Vitamin C Vitamin C may increase the adverse effects of deferoxamine. Transient deterioration of left ventricular function has been observed during concomitant therapy. Use caution during concomitant therapy.
Food Interactions Not Available
Targets

1. Iron

Pharmacological action: yes
Actions: chelator

References:
  1. 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
  2. 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
  3. Cappellini MD, Musallam KM, Taher AT: Overview of iron chelation therapy with desferrioxamine and deferiprone. Hemoglobin. 2009;33 Suppl 1:S58-69. Pubmed

2. Aluminum

Pharmacological action: yes
Actions: chelator

References:
  1. 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
  2. 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
  3. 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
  4. Domingo JL: The use of chelating agents in the treatment of aluminum overload. J Toxicol Clin Toxicol. 1989;27(6):355-67. Pubmed
Enzymes

1. Xanthine dehydrogenase/oxidase

Actions: inhibitor

This enzyme can be converted from the dehydrogenase form (D) to the oxidase form (O) irreversibly by proteolysis or reversibly through the oxidation of sulfhydryl groups

UniProt ID: P47989 Link_out
Gene: XDH Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19