ERUFOSINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H58NO4P
Molecular Weight	503.7382
Optical Activity	NONE
Defined Stereocenters	0 / 1
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-

HIDE SMILES / InChI

Molecular Formula	C28H58NO4P
Molecular Weight	503.7382
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	NONE

Approval Year

Substance Class	Chemical
Record UNII	W52C2EKX3F
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ERPC 3

Preferred Name

English

ERUFOSINE

Common Name

English

((Z)-DOCOS-13-ENYL) 3-(TRIMETHYL-$L^5-AZANYL)PROPYL HYDROGEN PHOSPHATE

Systematic Name

English

ERUCYLPHOSPHO-N,N,N-TRIMETHYLPROPYLAMMONIUM

Systematic Name

English

ERPC-3

Common Name

English

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Code System

Code

Type

Description

CAS

202867-33-2

PRIMARY

PUBCHEM

10323834

PRIMARY

FDA UNII

W52C2EKX3F

PRIMARY

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Related Record

Type

Details


					W52C2EKX3F

ERUFOSINE

ACTIVE MOIETY

Comments:

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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