Structure via PubChem · Public domain (PubChem)
edelfosine
Sign in to saveAlso known as 2-methoxy-3-(octadecyloxy)propyl 2-(trimethylammonio)ethyl phosphate
Edelfosine (ET-18-O-CH3; 1-octadecyl-2-O-methyl-glycero-3-phosphocholine) is a synthetic alkyl-lysophospholipid (ALP). It has antineoplastic (anti-cancer) effects.
Chemical data
- Formula
- C27H58NO6P
- Molecular weight
- 523.7 g/mol
- IUPAC name
- (2-methoxy-3-octadecoxypropyl) 2-(trimethylazaniumyl)ethyl phosphate
- SMILES
- CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC
- InChIKey
- MHFRGQHAERHWKZ-UHFFFAOYSA-N
- XLogP
- 7.6
- Polar surface area
- 77.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
566 papers- Edelfosine in membrane environment - the Langmuir monolayer studies.Anti-cancer agents in medicinal chemistry · 2014
- Edelfosine reactivates latent HIV-1 reservoirs in myeloid cells through activation of NF-κB and AP1 pathway.Virology · 2022
- Edelfosine: An Antitumor Drug Prototype.Anti-cancer agents in medicinal chemistry · 2018
- Lipid rafts, endoplasmic reticulum and mitochondria in the antitumor action of the alkylphospholipid analog edelfosine.Anti-cancer agents in medicinal chemistry · 2014
- Edelfosine nanoemulsions inhibit tumor growth of triple negative breast cancer in zebrafish xenograft model.Scientific reports · 2021
via PubMed
Wikidata facts
- Mass
- 523.4
Show 3 more facts
- chemical formula
- C₂₇H₅₈NO₆P
- subject has role
- phosphodiesterase inhibitor
- canonical SMILES
- CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
6 sectionsContents
- ''In vitro'' and ''in vivo'' results
- Clinical trials
- Toxicity
- History
- References
- Further reading
Edelfosine (ET-18-O-CH3; 1-octadecyl-2-O-methyl-glycero-3-phosphocholine) is a synthetic alkyl-lysophospholipid (ALP). It has antineoplastic (anti-cancer) effects.
Like all ALPs, it incorporates into the cell membrane and does not target the DNA. In many tumor cells, it causes selective apoptosis, sparing healthy cells. Edelfosine can activate the Fas/CD95 cell death receptor, can inhibit the MAPK/ERK mitogenic pathway and the Akt/protein kinase B (PKB) survival pathway. Aside from these plasma-level effects, edelfosine also affects gene expression by modulating the expression and activity of transcription factors.
Excerpted from Wikipedia’s “edelfosine” article, available under the CC BY-SA 4.0 licence.