Fumagillin (formerly known as NSC9168) is a novel, potent, selective and irreversible/covalent inhibitor of Methionine aminopeptidase 2 (MetAP2), it is primarily used as an antibiotic / antimicrobial to treat microsporidiosis. Fumagillin is a complex natural product antibiotic isolated in 1949 from the microbial organism Aspergillus fumigatus. It covalently binds a key histidine residue of methionine aminopeptidase type II (MetAP-2), inhibiting endothelial cell proliferation and angiogenesis. Fumagillin selectively inhibits the growth of a Δmap1 strain but not a wild-type or a Δmap2 S. cerevisiae strain missing MetAP-2.

Physicochemical Properties

Molecular Formula	C26H34O7
Molecular Weight	458.54
Exact Mass	458.23
Elemental Analysis	C, 68.10; H, 7.47; O, 24.42
CAS #	23110-15-8
Related CAS #	23110-15-8
PubChem CID	6917655
Appearance	White to light yellow solid powder
Density	1.19g/cm3
Boiling Point	608.8ºC at 760mmHg
Melting Point	>190ºC-192ºC
Flash Point	198.8ºC
Vapour Pressure	2.7E-16mmHg at 25°C
Index of Refraction	1.562
LogP	3.915
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	11
Heavy Atom Count	33
Complexity	879
Defined Atom Stereocenter Count	6
SMILES	C[C@]1([C@@H](CC=C(C)C)O1)[C@]([C@@H]2OC)([H])[C@]3(CC[C@H]2OC(/C=C/C=C/C=C/C=C/C(O)=O)=O)CO3
InChi Key	NGGMYCMLYOUNGM-IJIYPQOHSA-N
InChi Code	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
Chemical Name	(2E,4E,6E,8E)-10-(((3R,4S,5S,6R)-5-methoxy-4-((2R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-1-oxaspiro[2.5]octan-6-yl)oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
Synonyms	NSC9168; NSC 9168; NSC-9168; Fumidil B; trade names: Fumagilina; Fugillin; Fumidil.
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	HIV-1;Amebae
ln Vitro	Fumagillin selectively inhibits the growth of a Δmap1 strain but not a wild-type or a Δmap2 S. cerevisiae strain missing MetAP-2. In budding yeast cells, as a potent inhibitor of angiogenesis, Fumagillin not only reverses the growth inhibitory activity of Vpr, but also inhibits Vpr-dependent viral gene expression upon the infection of human macrophages. Though the toxicity of fumagillin has limited its use for human applications, the analogues using structure-activity relationships relating to its angiogenesis properties may be further explored in the treatment of angiogenesis-dependent diseases.
ln Vivo	In DEN-treated rats, fumagillin (30 mg/kg, i.p.) inhibits both progression of HCC in the liver itself and systemic metastasis.
Animal Protocol	30 mg/kg, i.p. Rats
References	[1]. Proc Natl Acad Sci U S A.1997 Jun 10;94(12):6099-103. [2]. World J Gastroenterol.2005 Feb 14;11(6):771-7. [3]. Expert Rev Anti Infect Ther, 2007. 5(4): p. 573-9. [4]. FEBS Lett. 2006 May 15;580(11):2598-602.
Additional Infomation	Fumagillin is a meroterpenoid resulting from the formal condensation of the hydroxy group of fumagillol with the carboxylic acid group of (all-E)-deca-2,4,6,8-tetraenedioic acid. Originally isolated from the fungus Aspergillus fumigatus, it is used for the control of Nosema infection in honey bees. It has a role as an angiogenesis inhibitor, an antibacterial drug, an antiprotozoal drug, a methionine aminopeptidase 2 inhibitor, an antimicrobial agent and a fungal metabolite. It is an organooxygen heterocyclic antibiotic, a meroterpenoid, a carboxylic ester, a dicarboxylic acid monoester, an antibiotic antifungal drug and a spiro-epoxide. It is functionally related to a fumagillol and an (all-E)-deca-2,4,6,8-tetraenedioic acid. Fumagillin has been reported in Aspergillus fumigatus and Aspergillus terreus with data available. See also: Bicyclohexylammonium Fumagillin (is active moiety of).

Solubility Data

Solubility (In Vitro)

DMSO : 92~ 250 mg/mL ( 200.63~545.21 mM ) H2O :< 0.1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.45 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (5.45 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (4.54 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (5.45 mM)  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.1808 mL	10.9042 mL	21.8083 mL
	5 mM	0.4362 mL	2.1808 mL	4.3617 mL
	10 mM	0.2181 mL	1.0904 mL	2.1808 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.