2860. Deferoxamine

Nomenclature

CAS number: 70-51-9
N′-[5-[[4-[[5-(Acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide; N-[5-[3-[(5-aminopentyl)hydroxycarbamoyl]propionamido]pentyl]-3-[[5-(N-hydroxyacetamido)pentyl]carbamoyl]propionohydroxamic acid; 1-amino-6,17-dihydroxy-7,10,18,21-tetraoxo-27-(N-acetylhydroxylamino)-6,11,17,22-tetraazaheptaeicosane; desferrioxamine B.
C25H48N6O8; mol wt 560.68.
C 53.55%, H 8.63%, N 14.99%, O 22.83%.

Description and references

Natural product forming iron complexes, isolated from Streptomyces pilosus Ettlinger et al. Prepn from ferrioxamine B and structure: H. Bickel et al., Helv. Chim. Acta 43, 2129 (1960). Syntheses: V. Prelog, A. Walser, ibid. 45, 631 (1962); BE 609053; E. Gaeumann et al., US 3471476 (l962, 1969 both to Ciba). Derivatives: H. Bickel et al., Helv. Chim. Acta 46, 1385 (1963). Interactions with cellular and plasma iron pools: J. B. Porter et al., Ann. N.Y. Acad. Sci. 1054, 155 (2005). Clinical efficacy in thallasemia major (Cooley's anemia): B. Modell et al., Br. Med. J. 284, 1081 (1982). Treatment of hemodialysis-induced aluminum accumulation in brain: P. Ackril et al, Lancet 2, 692 (1980); in bone: H. H. Malluche et al., N. Engl. J. Med. 311, 140 (1984). Neurotoxicity study: N. F. Olivieri et al., ibid. 314, 869 (1986). Review of clinical experience: R. Propper, D. Nathan, Annu. Rev. Med. 33, 509-519 (1982).

Chemical structure

Derivative

Monohydrate.

Nomenclature

CAS number: 25442-95-9

Properties

Crystals from dil alcohol, mp 138-140°. Sol in water at 20°: 1.2%.

Derivative

Hydrochloride.

Nomenclature

CAS number: 1950-39-6
Ba-29837.
C25H48N6O8.HCl; mol wt 597.14.
C 50.28%, H 8.27%, N 14.07%, O 21.43%, Cl 5.94%.

Properties

Crystals from slightly acidic methanol, mp 172-175°.

Derivative

Methanesulfonate.

Nomenclature

CAS number: 138-14-7
Desferrioxamine mesylate; DFOM; Desferal (Novartis).
C25H48N6O8.CH3SO3H; mol wt 656.79.
C 47.55%, H 7.98%, N 12.80%, O 26.80%, S 4.88%.

Properties

Crystals from dil alcohol, mp 148-149°. Sol in water at 20°: >20%. Slightly sol in methanol.

Derivative

N-Acetyl derivative.

Nomenclature

CAS number: 5722-48-5
N-Acetyldeferoxamine; N-acetyldesferrioxamine B.
C27H50N6O9; mol wt 602.72.
C 53.80%, H 8.36%, N 13.94%, O 23.89%.

Properties

Crystals from n-propanol, mp 180-182°.

Derivative

Iron complex.

Nomenclature

CAS number: 14836-73-8
Ferrioxamine B.
C25H45FeN6O8; mol wt 613.51.
C 48.94%, H 7.39%, Fe 9.10%, N 13.70%, O 20.86%.

Description and references

A natural microbial growth factor. Isoln: H. Bickel et al., Helv. Chim. Acta 43, 2118 (1960); E. Gaeumann et al., US 3118823; US 3153621 (both 1964 to Ciba).

Note

Reviews on iron-containing metabolites with growth stimulating properties, sideramines, or with antibiotic properties, sideromycins, ferrimycins: H. Bickel et al., Experientia 16, 129-133 (1960); V. Prelog, Pure Appl. Chem. 6, 327-338 (1963); F. Knüsel, J. Nüesch, Nature 206, 674-676 (l965); T. F. Emery, Adv. Enzymol. Relat. Areas Mol. Biol. 35, 135-185 (1971); Knüsel, Zimmermann, in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 653-667.

Therapeutic Category

Parenteral chelating agent (iron and aluminum). Methanesulfonate as antidote to iron poisoning.

Keywords

Antidote (Heavy Metal Poisoning); Chelating Agent