Fumagillin

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Fumagillin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	P01AX10 (WHO) Template:ATCvet;
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 ;
PubChem CID	6917655;
DrugBank	DB02640 ;
ChemSpider	5292885 ;
UNII	7OW73204U1;
ChEBI	CHEBI:48635 ;
ChEMBL	ChEMBL32838 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C26H34O7
Molar mass	458.54 g/mol
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 ; Key:NGGMYCMLYOUNGM-CSDLUJIJSA-N ;
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

Uses

In animals

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,^[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]

In humans

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.

Preliminary clinical trials are being conducted by Zafgen into using the fumagillin analog beloranib for weight loss.^[13]

According to Zbidah and coworkers from Germany fumagillin is toxic to erythrocytes in vitro.^[14]

Total synthesis

Fumagillin and the related fumagillol (the hydrolysis product) have been a target in total synthesis, with several reported successful strategies, racemic, asymmetric and formal.^[15]^[16]^[17]^[18]^[19]^[20]^[21]^[22]^[23]

References

↑ F. R. Hanson, T. E. Elbe, J. Bacteriol. 1949, 58, 527
↑ Williams, G.R., Sampson, M.A., Shutler, D., Rogers, R.E.L. (2008). "Does fumagillin control the recently detected invasive parasite Nosema ceranae in western honey bees (Apis mellifera)?". Journal of Invertebrate Pathology. 99 (3): 342–344. doi:10.1016/j.jip.2008.04.005. PMID 18550078.
↑ Sabin Russell (2007-04-26). "UCSF scientist tracks down suspect in honeybee deaths". San Francisco Chronicle.
↑ "Scientists Identify Pathogens That May Be Causing Global Honeybee Deaths" (Portable Document Format). Edgewood Chemical Biological Center. 2007-04-25.Template:Check
↑ Huang, Wei-Fone; Leellen Solter; Peter Yau; Brian Imai (7 March 2013). Schneider, David S, ed. "Nosema ceranae Escapes Fumagillin Control in Honey Bees". PLoS Pathogens. 9 (3): e1003185. doi:10.1371/journal.ppat.1003185.
↑ Xiaochun Chen et al. "Fumagillin and Fumarranol Interact with P. falciparum Methionine Aminopeptidase 2 and Inhibit Malaria Parasite Growth In Vitro and In Vivo". Chemistry & Biology, Vol. 16 Nr. 2 (2009) blz. 193-202. Template:Cite DOI
↑ Christopher Arico-Muendel et al. "Antiparasitic activities of novel, orally available fumagillin analogs". Bioorganic & Medicinal Chemistry Letters Vol. 19 Nr. 17 (2009), blz. 5128-5131 Template:Cite DOI
↑ Lanternier F, Boutboul D, Menotti J; et al. (February 2009). "Microsporidiosis in solid organ transplant recipients: two Enterocytozoon bieneusi cases and review". Transpl Infect Dis. 11 (1): 83–8. doi:10.1111/j.1399-3062.2008.00347.x. PMID 18803616.
↑ Molina JM, Tourneur M, Sarfati C; et al. (June 2002). "Fumagillin treatment of intestinal microsporidiosis". N. Engl. J. Med. 346 (25): 1963–9. doi:10.1056/NEJMoa012924. PMID 12075057.
↑ Lefkove B, Govindarajan B, Arbiser JL (August 2007). "Fumagillin: an anti-infective as a parent molecule for novel angiogenesis inhibitors". Expert Rev Anti Infect Ther. 5 (4): 573–9. doi:10.1586/14787210.5.4.573. PMID 17678422.
↑ Gilbert, M. A. & Granath, W.O. Jr. (2003). "Whirling disease and salmonid fish: life cycle, biology, and disease". Journal of Parasitology. 89 (4): pp. 658–667. doi:10.1645/GE-82R. PMID 14533670.
↑ Template:Cite DOI
↑ "Zafgen Announces Positive Topline Phase 1b Data for ZGN-433 in Obesity". MedNews. Drugs.com. 5 January 2011.
↑ Zbidah, M; Lupescu, A; Jilani, K; Lang, F (2013). "Stimulation of suicidal erythrocyte death by fumagillin". Basic & clinical pharmacology & toxicology. 112 (5): 346–51. doi:10.1111/bcpt.12033. PMID 23121865.
↑ Template:Cite DOI
↑ Template:Cite DOI
↑ A Concise Synthesis of Fumagillol David A. Vosburg, Sven Weiler, Erik J. Sorensen Angewandte Chemie International Edition Volume 38, Issue 7, Date: April 1, 1999, Pages: 971-974 DOI
↑ Template:Cite DOI
↑ Template:Cite DOI
↑ Template:Cite DOI
↑ Template:Cite DOI
↑ Template:Cite DOI
↑ Template:Cite DOI

[1] F. R. Hanson, T. E. Elbe, J. Bacteriol. 1949, 58, 527

[2] Williams, G.R., Sampson, M.A., Shutler, D., Rogers, R.E.L. (2008). "Does fumagillin control the recently detected invasive parasite Nosema ceranae in western honey bees (Apis mellifera)?". Journal of Invertebrate Pathology. 99 (3): 342–344. doi:10.1016/j.jip.2008.04.005. PMID 18550078.

[3] Sabin Russell (2007-04-26). "UCSF scientist tracks down suspect in honeybee deaths". San Francisco Chronicle.

[4] "Scientists Identify Pathogens That May Be Causing Global Honeybee Deaths" (Portable Document Format). Edgewood Chemical Biological Center. 2007-04-25.Template:Check

[5] Huang, Wei-Fone; Leellen Solter; Peter Yau; Brian Imai (7 March 2013). Schneider, David S, ed. "Nosema ceranae Escapes Fumagillin Control in Honey Bees". PLoS Pathogens. 9 (3): e1003185. doi:10.1371/journal.ppat.1003185.

[6] Xiaochun Chen et al. "Fumagillin and Fumarranol Interact with P. falciparum Methionine Aminopeptidase 2 and Inhibit Malaria Parasite Growth In Vitro and In Vivo". Chemistry & Biology, Vol. 16 Nr. 2 (2009) blz. 193-202. Template:Cite DOI

[7] Christopher Arico-Muendel et al. "Antiparasitic activities of novel, orally available fumagillin analogs". Bioorganic & Medicinal Chemistry Letters Vol. 19 Nr. 17 (2009), blz. 5128-5131 Template:Cite DOI

[pmid18803616-8] Lanternier F, Boutboul D, Menotti J; et al. (February 2009). "Microsporidiosis in solid organ transplant recipients: two Enterocytozoon bieneusi cases and review". Transpl Infect Dis. 11 (1): 83–8. doi:10.1111/j.1399-3062.2008.00347.x. PMID 18803616.

[pmid12075057-9] Molina JM, Tourneur M, Sarfati C; et al. (June 2002). "Fumagillin treatment of intestinal microsporidiosis". N. Engl. J. Med. 346 (25): 1963–9. doi:10.1056/NEJMoa012924. PMID 12075057.

[pmid17678422-10] Lefkove B, Govindarajan B, Arbiser JL (August 2007). "Fumagillin: an anti-infective as a parent molecule for novel angiogenesis inhibitors". Expert Rev Anti Infect Ther. 5 (4): 573–9. doi:10.1586/14787210.5.4.573. PMID 17678422.

[11] Gilbert, M. A. & Granath, W.O. Jr. (2003). "Whirling disease and salmonid fish: life cycle, biology, and disease". Journal of Parasitology. 89 (4): pp. 658–667. doi:10.1645/GE-82R. PMID 14533670.

[12] Template:Cite DOI

[13] "Zafgen Announces Positive Topline Phase 1b Data for ZGN-433 in Obesity". MedNews. Drugs.com. 5 January 2011.

[14] Zbidah, M; Lupescu, A; Jilani, K; Lang, F (2013). "Stimulation of suicidal erythrocyte death by fumagillin". Basic & clinical pharmacology & toxicology. 112 (5): 346–51. doi:10.1111/bcpt.12033. PMID 23121865.

[15] Template:Cite DOI

[16] Template:Cite DOI

[17] A Concise Synthesis of Fumagillol David A. Vosburg, Sven Weiler, Erik J. Sorensen Angewandte Chemie International Edition Volume 38, Issue 7, Date: April 1, 1999, Pages: 971-974 DOI

[18] Template:Cite DOI

[19] Template:Cite DOI

[20] Template:Cite DOI

[21] Template:Cite DOI

[22] Template:Cite DOI

[23] Template:Cite DOI

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