CAS 70-51-9|N'-[5-(Acetyl-hydroxy-amino)pentyl]-N-[5-[3-(5-aminopentyl-hydroxy-carbamoyl) propanoylamino]pentyl]-N-hydroxy-butane diamide|N-(5-aminopentyl)-N-hydroxy-N'-[5-(N-hydroxy-3-{[5-(N-hydrox...

General Information

Structure

Molecular Formula

C₂₅H₄₈N₆O₈

Molecular Mass

560.68402

Exact Mass

560.35336253

Charge

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

Canonic Smiles

NCCCCCN(C(=O)CCC(=O)NCCCCCN(C(=O)CCC(=O)NCCCCCN(C(=O)C)O)O)O

Isomeric Smiles

ON(CCCCCNC(=O)CCC(=O)N(O)CCCCCN)C(=O)CCC(=O)NCCCCCN(O)C(=O)C

Calculated Properties

JChem

LogD (pH = 7.4)

-3.64

LogD (pH = 5.5)

-4.90

Log P

-3.37

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

false

Acid pKa

10.23

Polar Surface Area

205.84

Polarizability

62.58

Molar Refractivity

144.95

LOG S

-0.17

Data Source

Names and Identifiers

Synonyms

N'-[5-(Acetyl-hydroxy-amino)pentyl]-N-[5-[3-(5-aminopentyl-hydroxy-carbamoyl) propanoylamino]pentyl]-N-hydroxy-butane diamideDeferoxamineDeferrioxamineDesferrioxamine BDeferoxamide BDeferrioxamine BDeferoxaminDeferoxaminumDeferoxamine BDFOADF BDFOMDFON-Benzoylferrioxamine BDesferrioxamineDeferoxamine mesylatedesferrioxamine-BDeferrioxamineDFOBDesferrioxamineDeferoxamindesferrioxamine BDFON(4)-{5-[acetyl(hydroxy)amino]pentyl}-N(1)-(5-{4-[(5-aminopentyl)(hydroxy)amino]-4-oxobutanamido}pentyl)-N(1)-hydroxybutanediamidedeferrioxamine B

IUPAC name

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

IUPAC Traditional name

deferoxamine

Brand Name

DesferrinDesferralDesferalDesferexDesferinDesferan

International Nonproprietary Name (INN)

deferoxaminumdeferoxaminedeferoxamina

Names and Identifiers

Registration numbers

PubChem SID

1609640894650639550139456

PubChem CID

DrugBank ID

KEGG ID

CAS Number

Wikipedia Title

Chemspider ID

Beilstein Number

ATC CODE

Unique Ingredient Identifier

J06Y7MXW4D

CHEBI ID

4356CHEBI:4356

CHEMBL

556CHEMBL556

BKMS React Database

232934998021736110589174729105890480846522

BRENDA Database

1.1.1.421.17.4.11.14.11.24.98.1.11.17.3.21.14.15.207.2.2.161.14.11.292.1.1.3551.14.99.291.14.16.41.1.98.61.13.11.631.6.5.2

Patent number

US2002155993US2002052422GB2240630US2001003001US2005142156US2001023240US2003012817US2004023847US2006264356US2005272638US2005042274US2004068013US2005119502US2002107266

SureChEMBL Database

SCHEMBL34571

BRENDA Ligand Database

499801058912329321736148081058907472946522

PubMed Citation Links

28285915283186973273445630701380312298363285636318536609310351973257274411239825320397782918227033784308318463152815612928455567

BindingDB Database

47715

MetaboLights Database

HMDB Database

UniProt Database

KEGG DRUG Database

ArrayExpress (Gene Expression Altlas)

E-GEOD-7835

Drug Central Database

LIPID MAPS Instance

LINCS Database

CompTox Database

ACToR Database

Registration numbers

Properties

Physical Property

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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]

An acyclic desferrioxamine that is butanedioic acid in which one of the carboxy groups undergoes formal condensation with the primary amino group of N-(5-aminopentyl)-N-hydroxyacetamide and the second carboxy group undergoes formal condensation with the hydroxyamino group of N(1)-(5-aminopentyl)-N(1)-hydroxy-N(4)-[5-(hydroxyamino)pentyl]butanediamide. It is a siderophore native to Streptomyces pilosus biosynthesised by the DesABCD enzyme cluster as a high affinity Fe(III) chelator.

Molecule Details

References

PubChem Literature

From Data Sources

• Link

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

deferoxamine

Brand Name

DesferrinDesferralDesferalDesferexDesferinDesferan

International Nonproprietary Name (INN)

deferoxaminumdeferoxaminedeferoxamina

Properties

Physical Property

Molecule Details

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

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

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]

References

PubChem Literature

From Data Sources