Title: Fumagillin

CAS Registry Number: 23110-15-8

CAS Name: (2E,4E,6E,8E)-2,4,6,8-Decatetraenedioic acid mono[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester

Additional Names: 2,4,6,8-decatetraenedioic acid mono[4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl] ester

Molecular Formula: C26H34O7

Molecular Weight: 458.54

Percent Composition: C 68.10%, H 7.47%, O 24.42%

Literature References: Antibiotic substance produced by Aspergillus fumigatus: T. E. Eble, F. R. Hanson, Antibiot. Chemother. 1, 55 (1951); F. R. Hanson, T. E. Eble, US 2652356 (1953 to Upjohn). Purification: D. S. Tarbell et al., J. Am. Chem. Soc. 77, 5613 (1955). Structure: eidem, ibid. 82, 1005 (1960); 83, 3096 (1961). Stereochemistry: N. J. McCorkindale, J. G. Sime, Proc. Chem. Soc. London 1961, 331; J. R. Turner, D. S. Tarbell, Proc. Natl. Acad. Sci. USA 48, 733 (1962). Biosynthesis: A. J. Birch, S. F. Hussain, J. Chem. Soc. C 1969, 1473. Total synthesis of (±)-form: E. J. Corey, B. B. Snider, J. Am. Chem. Soc. 94, 2549 (1972). Anti-amebic activity: M. C. McCowen et al., Science 113, 202 (1951). Acute toxicity: J. A. DiPaolo et al., Antibiot. Annu. 1958-1959, 541. HPLC determn in trout muscle: J. Guyonnet et al., J. Chromatogr. B 666, 354 (1995). Field trial in honey bees: T. C. Webster, J. Econ. Entomol. 87, 601 (1994); in rainbow trout: R. le Gouvello et al., Aquaculture 171, 27 (1999). Clinical evaluation in intestinal microsporidiosis in immunocompromised patients: J.-M. Molina et al., N. Engl. J. Med. 346, 1963 (2002).

Properties: Yellow needles from methanol, mp 194-195°. [a]D25 -26.6° (c = 1 in 95% ethanol). Absorptivity: 156.0 at 335 nm and 146.5 at 351 nm (soln of 100 mg in 10 ml chloroform diluted with alcohol to 0.0004% fumagillin and 0.04% chloroform). Practically insol in water, dil acids, satd hydrocarbons. Sol in most other organic solvents, in aq solns of bicarbonates and alkali hydroxides. Best stored in dark, evacuated ampuls at low temps. Stability data: T. E. Eble, E. R. Garrett, J. Am. Pharm. Assoc. 43, 536 (1954); E. R. Garrett, ibid. 539. LD50 in mice (mg/kg): ~800 s.c. (DiPaolo).

Melting point: mp 194-195°

Optical Rotation: [a]D25 -26.6° (c = 1 in 95% ethanol)

Toxicity data: LD50 in mice (mg/kg): ~800 s.c. (DiPaolo)

 

Derivative Type: Dicyclohexylamine salt

CAS Registry Number: 41567-78-6

Additional Names: Bicyclohexylammonium fumagillin

Trademarks: Fumidil B (Sanofi)

 

Therap-Cat: Antiprotozoal.

Therap-Cat-Vet: Antiprotozoal. Control of Nosema apis in honey bees.

Keywords: Antiamebic.