Fumagillin

Fumagillin

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	P01AX10 (WHO) QP51AX23 (WHO)
Identifiers
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
CAS Number	23110-15-8 Y
PubChem CID	6917655
DrugBank	DB02640 N
ChemSpider	5292885 N
UNII	7OW73204U1
ChEBI	CHEBI:48635 N
ChEMBL	CHEMBL32838 N
ECHA InfoCard	100.041.288
Chemical and physical data
Formula	C26H34O7
Molar mass	458.54 g/mol
3D model (Jmol)	Interactive image
SMILES CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)OC(=O)/C=C/C=C/C=C/C=C/C(=O)O)OC)C
InChI InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20-,23-,24-,25+,26+/m1/s1 N Key:NGGMYCMLYOUNGM-CSDLUJIJSA-N N
NY (what is this?)

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

It was originally used against microsporidial parasites Nosema apis infections in honey bees.

Some studies found it to be effective against some myxozoan parasites, including Myxobolus cerebralis, an important parasite of fish; however, in the more rigorous tests required for U.S. Food and Drug Administration approval, it was ineffective.

There are reports that fumagillin controls Nosema ceranae, which has recently been hypothesized as a possible cause of colony collapse disorder. The latest report, however, has shown it to be ineffective against N. ceranae. Fumagillin is also investigated as an inhibitor of malaria parasite growth.

Fumagillin has been used in the treatment of microsporidiosis. It is also an amebicide.

Fumagillin can block blood vessel formation by binding to an enzyme methionine aminopeptidase 2 and for this reason, the compound, together with semisynthetic derivatives, are investigated as an angiogenesis inhibitor in the treatment of cancer.

Preliminary clinical trials are being conducted by Zafgen into using the fumagillin analog beloranib for weight loss.

According to Zbidah and coworkers from Germany fumagillin is toxic to erythrocytes in vitro at concentrations >10uM.

Fumagillin and the related fumagillol (the hydrolysis product) have been a target in total synthesis, with several reported successful strategies, racemic, asymmetric and formal.