Fumagillin

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.
Fumaric Acid Fumigatin Fungichromin Fungisterol Funtumine

Fumagillin
Fumagillin structure.svg
Systematic (IUPAC) name
(2E,4E,6E,8E)-10-{[(3R,4S,5S,6R)-5-methoxy- 4-[(2R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1- oxaspiro[2.5]octan-6-yl]oxy}-10 -oxodeca-2,4,6,8-tetraenoic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 23110-15-8 YesY
ATC code P01AX10 QP51AX23
PubChem CID 6436022
DrugBank DB02640
UNII 7OW73204U1 YesY
ChEBI CHEBI:48635 N
ChEMBL CHEMBL1744445 N
Chemical data
Formula C26H34O7 
Mol. mass 458.54 g/mol
 N (what is this?)  (verify)

Fumagillin is a complex biomolecule and used as an antimicrobial agent. It was isolated in 1949 from the microbial organism Aspergillus fumigatus.[1]