Deferoxamine
Title: Deferoxamine
CAS Registry Number: 70-51-9
CAS Name: N¢-[5-[[4-[[5-(Acetylhydroxyamino)pentyl]amino]-1,4-dioxobutyl]hydroxyamino]pentyl]-N-(5-aminopentyl)-N-hydroxybutanediamide
Additional Names: 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
Molecular Formula: C25H48N6O8
Molecular Weight: 560.68
Percent Composition: C 53.55%, H 8.63%, N 14.99%, O 22.83%
Literature 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). 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).
 
Derivative Type: Monohydrate
Properties: Crystals from dil alcohol, mp 138-140°. Sol in water at 20°: 1.2%.
Melting point: mp 138-140°
 
Derivative Type: Hydrochloride
CAS Registry Number: 1950-39-6
Manufacturers' Codes: Ba-29837
Molecular Formula: C25H48N6O8.HCl
Molecular Weight: 597.14
Percent Composition: C 50.28%, H 8.27%, N 14.07%, O 21.43%, Cl 5.94%
Properties: Crystals from slightly acidic methanol, mp 172-175°.
Melting point: mp 172-175°
 
Derivative Type: Methanesulfonate
CAS Registry Number: 138-14-7
Additional Names: Desferrioxamine mesylate; DFOM
Trademarks: Desferal (Novartis)
Molecular Formula: C25H48N6O8.CH3SO3H
Molecular Weight: 656.79
Percent Composition: 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%.
Melting point: mp 148-149°
 
Derivative Type: N-Acetyl derivative
Additional Names: N-Acetyldeferoxamine; N-acetyldesferrioxamine B
Molecular Formula: C27H50N6O9
Molecular Weight: 602.72
Percent Composition: C 53.80%, H 8.36%, N 13.94%, O 23.89%
Properties: Crystals from n-propanol, mp 180-182°.
Melting point: mp 180-182°
 
Derivative Type: Iron complex
Additional Names: Ferrioxamine B
Molecular Formula: C25H45FeN6O8
Molecular Weight: 613.51
Percent Composition: C 48.94%, H 7.39%, Fe 9.10%, N 13.70%, O 20.86%
Literature 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.
Therap-Cat: Parenteral chelating agent (iron and aluminum). Methanesulfonate as antidote to iron poisoning.
Keywords: Antidote (Heavy Metal Poisoning); Chelating Agent.

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