Identification

Generic Name
Fumagillin
DrugBank Accession Number
DB02640
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 458.551
Monoisotopic: 458.230453435
Chemical Formula
C26H34O7
Synonyms
  • fumagilina
  • Fumagillin

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMethionine aminopeptidase 2
ligand
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Alendronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Fumagillin is combined with Alendronic acid.
Clodronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Fumagillin is combined with Clodronic acid.
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Fumagillin.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Fumagillin.
Etidronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Fumagillin is combined with Etidronic acid.
IbandronateThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Fumagillin is combined with Ibandronate.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Fumagillin.
Pamidronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Fumagillin is combined with Pamidronic acid.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Fumagillin.
Risedronic acidThe risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Fumagillin is combined with Risedronic acid.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Flisint (Sanofi) / Fugillin (Upjohn) / Furnidil (Abbott)

Categories

ATC Codes
P01AX10 — Fumagillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Medium-chain fatty acids
Alternative Parents
Fatty acid esters / Epoxy fatty acids / Branched fatty acids / Unsaturated fatty acids / Dicarboxylic acids and derivatives / Enoate esters / Oxacyclic compounds / Epoxides / Dialkyl ethers / Carboxylic acids
show 3 more
Substituents
Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated carboxylic ester / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Dicarboxylic acid or derivatives / Enoate ester
show 13 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
dicarboxylic acid monoester, antibiotic antifungal drug, carboxylic ester, epoxide, organooxygen heterocyclic antibiotic, oxaspiro compound, meroterpenoid (CHEBI:48635) / Bisabolane sesquiterpenoids (LMPR0103060003)
Affected organisms
Not Available

Chemical Identifiers

UNII
7OW73204U1
CAS number
23110-15-8
InChI Key
NGGMYCMLYOUNGM-CSDLUJIJSA-N
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
IUPAC Name
(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]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
SMILES
CO[C@@H]1[C@@H](CC[C@]2(CO2)[C@H]1[C@@]1(C)O[C@@H]1CC=C(C)C)OC(=O)\C=C\C=C\C=C\C=C\C(O)=O

References

Synthesis Reference

Peterson, M.H., Goldstein, A.W. and Denison, F.W. Jr.; U.S. Patent 2,803,586; August 20, 1957; assigned to Abbott Laboratories.

General References
Not Available
KEGG Compound
C09668
PubChem Compound
6917655
PubChem Substance
46505331
ChemSpider
5292885
BindingDB
50113436
ChEBI
48635
ChEMBL
CHEMBL32838
ZINC
ZINC000004098264
Therapeutic Targets Database
DNC000664
PDBe Ligand
FUG
Wikipedia
Fumagillin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)190-192Peterson, M.H., Goldstein, A.W. and Denison, F.W. Jr.; U.S. Patent 2,803,586; August 20, 1957; assigned to Abbott Laboratories.
Predicted Properties
PropertyValueSource
Water Solubility0.0033 mg/mLALOGPS
logP4.61ALOGPS
logP4.05ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area97.89 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity128.37 m3·mol-1ChemAxon
Polarizability51.13 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.907
Blood Brain Barrier-0.5281
Caco-2 permeable-0.578
P-glycoprotein substrateSubstrate0.7621
P-glycoprotein inhibitor IInhibitor0.5957
P-glycoprotein inhibitor IIInhibitor0.8966
Renal organic cation transporterNon-inhibitor0.9216
CYP450 2C9 substrateNon-substrate0.8485
CYP450 2D6 substrateNon-substrate0.8869
CYP450 3A4 substrateSubstrate0.639
CYP450 1A2 substrateNon-inhibitor0.8839
CYP450 2C9 inhibitorNon-inhibitor0.7431
CYP450 2D6 inhibitorNon-inhibitor0.9299
CYP450 2C19 inhibitorNon-inhibitor0.7701
CYP450 3A4 inhibitorNon-inhibitor0.7188
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9386
Ames testAMES toxic0.6248
CarcinogenicityNon-carcinogens0.9203
BiodegradationNot ready biodegradable0.8205
Rat acute toxicity2.7268 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9914
hERG inhibition (predictor II)Non-inhibitor0.9147
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Poly(a) rna binding
Specific Function
Cotranslationally removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala...
Gene Name
METAP2
Uniprot ID
P50579
Uniprot Name
Methionine aminopeptidase 2
Molecular Weight
52891.145 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51