Details
Stereochemistry | ACHIRAL |
Molecular Formula | C28H58NO4P |
Molecular Weight | 503.7382 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C/CCCCCCCCCCCCOP([O-])(=O)OCCC[N+](C)(C)C
InChI
InChIKey=JRNJGNRNGUZCTF-SEYXRHQNSA-N
InChI=1S/C28H58NO4P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-27-32-34(30,31)33-28-25-26-29(2,3)4/h12-13H,5-11,14-28H2,1-4H3/b13-12-
Molecular Formula | C28H58NO4P |
Molecular Weight | 503.7382 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Approval Year
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:43:09 GMT 2023
by
admin
on
Sat Dec 16 11:43:09 GMT 2023
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Record UNII |
W52C2EKX3F
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Record Status |
Validated (UNII)
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Record Version |
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-
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202867-33-2
Created by
admin on Sat Dec 16 11:43:09 GMT 2023 , Edited by admin on Sat Dec 16 11:43:09 GMT 2023
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10323834
Created by
admin on Sat Dec 16 11:43:09 GMT 2023 , Edited by admin on Sat Dec 16 11:43:09 GMT 2023
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W52C2EKX3F
Created by
admin on Sat Dec 16 11:43:09 GMT 2023 , Edited by admin on Sat Dec 16 11:43:09 GMT 2023
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
The compounds edelfosine, miltefosine, perifosine, and erufosine are alkylphospholipids with the distinction that edelfosine is an alkyl-lysophospholipid and the other three molecules belong to a subclass of alkylphosphocholines (Fig. 1). The cytotoxicity of edelfosine, miltefosine, perifosine, and erufosine were directly compared in half-log increments from 3 to 300 .MU.M concentrations in both mouse and human bone marrow in CFU-GM assays. The cells were exposed continuously to the agents for 1416 days. The IC50 and IC90 values in the mouse CFU-GM assay were higher for erufosine (170.4 +/- 11.5 .MU.M, 288.3 +/- 5.2 .MU.M) than for edelfosine (29.4 +/- 7.8 .MU.M, 76.7 +/- 17.7 .MU.M), miltefosine (111.7 +/- 19.3 .MU.M, 194.5 +/- 42.2 .MU.M), and perifosine (120.8 +/- 35.2 .MU.M,237.2 +/- 34.3 .MU.M) (Table 1, Fig. 2a). Erufosine was less toxic to murine bone marrow cells in particular at the 100 .MU.M concentration. In the human CFU-GM assay, the IC50 and IC90 values for erufosine (216.0 +/- 3.1 .MU.M, 284.3 +/- 3.0 .MU.M) were also higher than for the miltefosine (31.7 +/- 1.7 .MU.M, 118.3 +/- 20.9 .MU.M) and perifosine (<3 .MU.M, 83.3 +/- 4.4 .MU.M) (Table 1, Fig. 2b). The differences between erufosine and miltefosine and perifosine were noticeable across concentrations ranging from 10 to 100 .MU.M. Although edelfosine was tested in the assay, the edelfosine altered the methylcellulose semisolid matrix medium for the human CFU-GM assay so that it was more liquid thereby preventing any countable colony formation.
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