fumagillin

Names

[ Name ]:
fumagillin

[Synonym ]:
FUGILLIN
FUMADIL B
amebacillin
(2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)-2-oxiranyl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxo-2,4,6,8-decatetraenoic acid
fumagillin
(2E,4E,6E,8E)-10-({(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]oct-6-yl}oxy)-10-oxodeca-2,4,6,8-tetraenoic acid
EINECS 245-433-8
MFCD03990453
fumidil
h-3
FUMIDIL B
AMEBACILIN
2,4,6,8-Decatetraenedioic acid, mono[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-buten-1-yl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl] ester, (2E,4E,6E,8E)-
mono[5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]octan-6-yl]ester
fugilin

Biological Activity

[Description]:

Fumagillin(NSC9168) is a complex biomolecule and used as an antimicrobial agent.Target: AntiparasiticFumagillin is an active amebicide and anti-infective isolated from the fungus Aspergillus fumigatus. Fumagillin does exhibit some side effects that have deterred its acceptance as a viable treatment, but the current body of research on the synthesis of novel analogs of this molecule shows an exciting and promising revival of this drug as both an anti-infective and antiangiogenic agent [1].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Parasite

Research Areas >> Infection

[References]

[1]. Lefkove, B., B. Govindarajan, and J.L. Arbiser, Fumagillin: an anti-infective as a parent molecule for novel angiogenesis inhibitors. Expert Rev Anti Infect Ther, 2007. 5(4): p. 573-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.19g/cm3

[ Boiling Point ]:
608.8ºC at 760mmHg

[ Melting Point ]:
>190ºC-192ºC

[ Molecular Formula ]:
C₂₆H₃₄O₇

[ Molecular Weight ]:
458.54400

[ Flash Point ]:
198.8ºC

[ Exact Mass ]:
458.23000

[ PSA ]:
97.89000

[ LogP ]:
3.91540

[ Vapour Pressure ]:
2.7E-16mmHg at 25°C

[ Index of Refraction ]:
1.562

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HE1750000

CHEMICAL NAME :: 2,4,6,8-Decatetraenedioic acid, 4-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-5-methoxy-1- oxaspiro(2,5)oct-6-yl ester

CAS REGISTRY NUMBER :: 23110-15-8

LAST UPDATED :: 199309

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C26-H34-O7

MOLECULAR WEIGHT :: 458.60

WISWESSER LINE NOTATION :: BT3OTJ B C2UY

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 3,1834,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 1,54,1951 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 25 mg/kg

SEX/DURATION :: female 11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: 85DJA5 "Malformations Congenitales des Mammiferes," Tuchmann-Duplessis, H., Paris, Masson et Cie, 1971 Volume(issue)/page/year: -,95,1971

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302-H312-H319-H332

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
36

[ RIDADR ]:
UN 1648 3 / PGII

[ WGK Germany ]:
3

[ RTECS ]:
HE1750000

[ HS Code ]:
29419090

Preparation

Articles

Fumagillin prodrug nanotherapy suppresses macrophage inflammatory response via endothelial nitric oxide.

ACS Nano 8(7) , 7305-17, (2014)

Antiangiogenesis has been extensively explored for the treatment of a variety of cancers and certain inflammatory processes. Fumagillin, a mycotoxin produced by Aspergillus fumigatus that binds methio...

Early treatment with fumagillin, an inhibitor of methionine aminopeptidase-2, prevents Pulmonary Hypertension in monocrotaline-injured rats.

PLoS ONE 7(4) , e35388, (2012)

Pulmonary Hypertension (PH) is a pathophysiologic condition characterized by hypoxemia and right ventricular strain. Proliferation of fibroblasts, smooth muscle cells, and endothelial cells is central...

The Aspergillus fumigatus toxin fumagillin suppresses the immune response of Galleria mellonella larvae by inhibiting the action of haemocytes.

Microbiology 157(Pt 5) , 1481-8, (2011)

Larvae of Galleria mellonella are widely used to evaluate microbial virulence and to assess the in vivo efficacy of antimicrobial agents. The aim of this work was to examine the ability of an Aspergil...