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Details

Stereochemistry RACEMIC
Molecular Formula C27H58NO6P
Molecular Weight 523.7263
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EDELFOSINE

SMILES

CCCCCCCCCCCCCCCCCCOCC(COP([O-])(=O)OCC[N+](C)(C)C)OC

InChI

InChIKey=MHFRGQHAERHWKZ-UHFFFAOYSA-N
InChI=1S/C27H58NO6P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-32-25-27(31-5)26-34-35(29,30)33-24-22-28(2,3)4/h27H,6-26H2,1-5H3

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12369895 | https://www.ncbi.nlm.nih.gov/pubmed/24448421 | https://www.ncbi.nlm.nih.gov/pubmed/19188156 | https://www.ncbi.nlm.nih.gov/pubmed/9131178

Edelfosine is a synthetic alkyl-lysophospholipid, a potent immunomodulator and an effective inhibitor of tumor cell proliferation. The cytotoxic effect of edelfosine has been evaluated in a large variety of both tumor (leukemic and solid) and normal cell types, showing a high degree of selectivity towards tumor cells. Like all alkyl-lysophospholipids, Edelfosine incorporates into the cell membrane and does not target the DNA. In many tumor cells, Edelfosine causes selective apoptosis, sparing healthy cells. Edelfosine can activate the Fas/CD95cell death receptor, can inhibit the MAPK/ERK mitogenic pathway and the Akt/protein kinase B (PKB) survival pathway. Edelfosine apoptosis-inducing abilities were studied with several types of cancer, among them multiple myeloma and non-small and small cell lung carcinoma cell lines. In vivo activity against human solid tumors in mice was shown against malignant gynecological tumor cells, like ovarian cancer, and against breast cancer. In vivo biodistribution studies demonstrated a “considerably higher” accumulation of Edelfosine in tumor cells than in other analyzed organs. Several clinical trials were conducted. Among them, a phase I trials with solid tumors or leukemias and phase II with non-small-cell lung carcinomas (NSCLC). In Phase II clinical trial for use of Edelfosine in treating leukemia with bone marrow transplants, it was found to be safe and 'possibly effective'. A phase II trial for the treatment of brain cancers was also reported. It showed encouraging results in stopping the growth of the tumor and a considerable improvement in the “quality of life” of the patients. A phase II trial on the effect of Edelfosine on advanced non-small-cell bronchogenic carcinoma had a “remarkable” “high proportion of patients with stationary tumor status” as result, stable disease after initial progression in 50% of the patients.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.5 µM [IC50]
1.8 µM [IC50]
12.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.46 μg/mL
600 μg 1 times / day multiple, oral
dose: 600 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EDELFOSINE plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
258.241 μg × h/mL
600 μg 1 times / day multiple, oral
dose: 600 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EDELFOSINE plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
30.404 h
600 μg 1 times / day multiple, oral
dose: 600 μg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EDELFOSINE plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
In vitro evaluation of phosphocholine and quaternary ammonium containing lipids as novel anti-HIV agents.
1991 Apr
Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity.
1991 Apr
Protein kinase CbetaII activation by 1-beta-D-arabinofuranosylcytosine is antagonistic to stimulation of apoptosis and Bcl-2alpha down-regulation.
1997 Sep 19
Sensitization of TRPA1 by PAR2 contributes to the sensation of inflammatory pain.
2007 Jul
Leptin excites proopiomelanocortin neurons via activation of TRPC channels.
2010 Jan 27
Patents

Sample Use Guides

A group of BALB/c mice and a group of SCID non–tumor-bearing mice were treated with a daily oral administration of 30 mg/kg edelfosine for 6 d.
Route of Administration: Oral
Edelfosine treatment of THP-1 cells was performed during the logarithmic growth phase at a concentration of 4 x10^5 cells/mL at 37 C and 5% CO2 for 24 h. The percentage of living cells was evaluated by flow cytometry by the propidium iodide (PI) exclusion method.
Name Type Language
EDELFOSINE
INN  
INN  
Official Name English
CHOLINE HYDROXIDE, (±)-2-METHOXY-3-(OCTADECYLOXY)PROPYL HYDROGEN PHOSPHATE, INNER SALT
Common Name English
NSC-343649
Code English
ET-18-OME
Code English
3,5,9-TRIOXA-4-PHOSPHAHEPTACOSAN-1-AMINIUM, 4-HYDROXY-7-METHOXY-N,N,N-TRIMETHYL-, INNER SALT, 4-OXIDE, (±)-
Common Name English
NSC-324368
Code English
edelfosine [INN]
Common Name English
3,5,9-TRIOXA-4-PHOSPHAHEPTACOSAN-1-AMINIUM, 4-HYDROXY-7-METHOXY-N,N,N-TRIMETHYL-, INNER SALT, 4-OXIDE
Systematic Name English
RACEMIC 1-O-OCTADECYL-2-O-METHYLGLYCERO-3-PHOSPHOCHOLINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C277
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
NCI_THESAURUS C2089
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
Code System Code Type Description
NSC
324368
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
CAS
119225-10-4
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
SUPERSEDED
SMS_ID
100000080490
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
CAS
70641-51-9
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
CAS
122130-64-7
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
SUPERSEDED
CAS
195154-26-8
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
SUPERSEDED
INN
6296
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
FDA UNII
1Y6SNA8L5S
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
NCI_THESAURUS
C956
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
NSC
343649
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
EVMPD
SUB06455MIG
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
CHEBI
78649
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL28509
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
PUBCHEM
1392
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID9045766
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
MESH
C026659
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
WIKIPEDIA
EDELFOSINE
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
PRIMARY
CAS
65492-82-2
Created by admin on Fri Dec 15 15:37:28 GMT 2023 , Edited by admin on Fri Dec 15 15:37:28 GMT 2023
SUPERSEDED