Fumagillin
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Identification
- Generic Name
- Fumagillin
- DrugBank Accession Number
- DB02640
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 458.551
Monoisotopic: 458.230453435 - Chemical Formula
- C26H34O7
- Synonyms
- fumagilina
- Fumagillin
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UMethionine aminopeptidase 2 ligandHumans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAlendronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Fumagillin is combined with Alendronic acid. Ambroxol The risk or severity of methemoglobinemia can be increased when Fumagillin is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Fumagillin is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Fumagillin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Fumagillin is combined with Benzyl alcohol. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- 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
- External Links
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 190-192 Peterson, 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
Property Value Source Water Solubility 0.0033 mg/mL ALOGPS logP 4.61 ALOGPS logP 4.05 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 4.88 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 97.89 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 128.37 m3·mol-1 Chemaxon Polarizability 51.13 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.907 Blood Brain Barrier - 0.5281 Caco-2 permeable - 0.578 P-glycoprotein substrate Substrate 0.7621 P-glycoprotein inhibitor I Inhibitor 0.5957 P-glycoprotein inhibitor II Inhibitor 0.8966 Renal organic cation transporter Non-inhibitor 0.9216 CYP450 2C9 substrate Non-substrate 0.8485 CYP450 2D6 substrate Non-substrate 0.8869 CYP450 3A4 substrate Substrate 0.639 CYP450 1A2 substrate Non-inhibitor 0.8839 CYP450 2C9 inhibitor Non-inhibitor 0.7431 CYP450 2D6 inhibitor Non-inhibitor 0.9299 CYP450 2C19 inhibitor Non-inhibitor 0.7701 CYP450 3A4 inhibitor Non-inhibitor 0.7188 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9386 Ames test AMES toxic 0.6248 Carcinogenicity Non-carcinogens 0.9203 Biodegradation Not ready biodegradable 0.8205 Rat acute toxicity 2.7268 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9914 hERG inhibition (predictor II) Non-inhibitor 0.9147
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00kf-0120900000-6242e5e5fc33fa9d1198 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-01pk-0902500000-10fd1d98f3f3aecc912b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001j-1923200000-5fffcc2fd23546287254 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05mp-1513900000-54a135545a3416a2a89c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-007a-1954100000-33df0b0325fa30bfd2f3 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-1900100000-8e5ec327221ff6e42b2d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 248.2091933 predictedDarkChem Lite v0.1.0 [M-H]- 259.8984046 predictedDarkChem Lite v0.1.0 [M-H]- 263.7745046 predictedDarkChem Lite v0.1.0 [M-H]- 209.57625 predictedDeepCCS 1.0 (2019) [M+H]+ 244.4569097 predictedDarkChem Lite v0.1.0 [M+H]+ 260.2714046 predictedDarkChem Lite v0.1.0 [M+H]+ 265.0598046 predictedDarkChem Lite v0.1.0 [M+H]+ 211.47166 predictedDeepCCS 1.0 (2019) [M+Na]+ 245.8557046 predictedDarkChem Lite v0.1.0 [M+Na]+ 260.7484046 predictedDarkChem Lite v0.1.0 [M+Na]+ 217.22737 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
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1. DetailsMethionine aminopeptidase 2
- 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
- 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