Contents

Fumagillin

Chemical compound

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
CompTox Dashboard (EPA)	DTXSID7040736
ECHA InfoCard	100.041.288
Chemical and physical data
Formula	C26H34O7
Molar mass	458.551 g·mol−1
3D model (JSmol)	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?)  (verify)

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

It was originally used against microsporidian parasites Nosema apis infections in honey bees.^{[citation needed]}

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.^{[citation needed]}

There are reports that fumagillin controls Nosema ceranae,^[2] which has recently been hypothesized as a possible cause of colony collapse disorder.^[3][4] The latest report, however, has shown it to be ineffective against N. ceranae.^[5] Fumagillin is also investigated as an inhibitor of malaria parasite growth.^[6][7]

Fumagillin has been used in the treatment of microsporidiosis.^[8][9] It is also an amebicide.^[10]

Fumagillin can block blood vessel formation by binding to an enzyme methionine aminopeptidase 2^[11] and for this reason, the compound, together with semisynthetic derivatives, are investigated as an angiogenesis inhibitor^[12] in the treatment of cancer.

The company Zafgen conducted clinical trials using the fumagillin analog beloranib for weight loss,^[13] but they were unsuccessful.^[14]

Fumagillin is toxic to erythrocytes in vitro at concentrations greater than 10 μM.^[15]

Fumagillin and the related fumagillol (the hydrolysis product) have been a target in total synthesis, with several reported successful strategies, racemic, asymmetric, and formal.^{[16][17][18][19][20][21][22][23][24]}