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I2409

Sigma-Aldrich

Ilmofosine

≥97% (NMR), semisolid (waxy)

Synonym(s):

1-Hexadecylmercapto-2-methoxymethyl-3-propyl phosphoric acid monocholine ester, BM 41.440

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About This Item

Empirical Formula (Hill Notation):
C26H56NO5PS
CAS Number:
83519-04-4
Molecular Weight:
525.77
MDL number:
MFCD00869023
UNSPSC Code:
12352202
PubChem Substance ID:
24724510
NACRES:
NA.77

Assay

≥97% (NMR)

form

semisolid (waxy)

solubility

H2O: 10 mg/mL

originator

Roche

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCCSCC(COC)COP([O-])(=O)OCC[N+](C)(C)C

InChI

1S/C26H56NO5PS/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22-34-25-26(23-30-5)24-32-33(28,29)31-21-20-27(2,3)4/h26H,6-25H2,1-5H3

InChI key

ODEDPKNSRBCSDO-UHFFFAOYSA-N

Biochem/physiol Actions

Protein Kinase C (PKC) inhibitor; an ether lipid derivative of lysophosphatidylcholine has antineoplastic activity in vitro and in vivo. IC50 = 560 nM. Competitive at the regulatory site of PKC. Ilmofosine is active against a variety of explanted human non-small cell lung, breast, colorectal, ovarian, renal cell cancer, and melanoma tumors in vitro at concentrations of 1-30 μg/mL.

Features and Benefits

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Packaging

Air-sensitive, sealed under nitrogen

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
065K4612V
065K4612

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S Azzouz et al.
Parasite (Paris, France), 16(3), 215-221 (2009-10-21)
We studied the stress proteins induced in protozoa Leishmania donovani after treatment with edelfosine, miltefosine and ilmofosine. We studied the morphological and structural modifications caused in the promastigote forms of the parasite after treatment with the three alkyl-lysophospholipids (ALPs). A
P V Woolley et al.
Investigational new drugs, 14(2), 219-222 (1996-01-01)
We have conducted a study of ilmofosine (1-hexadecylthio; 2-methoxyethyl-rac-glycero-3-phosphocholine) in non-small cell bronchogenic carcinoma, using a schedule of continuous infusion for 5 days and a dose of 300 mg/m2/day. Toxicities were gastrointestinal (nausea, vomiting, diarrhea), fatigue and liver function abnormalities.
S Azzouz et al.
The Journal of parasitology, 92(5), 877-883 (2006-12-13)
To discover the mode of action of alkyl-lysophospholipids in Leishmania donovani, we studied the effects of edelfosine, miltefosine, and ilmofosine on intracellular pH, the parasite's cell cycle, and the induction of apoptosis. The effect of the alkyl-lysophospholipids was combined with
E A Fleer et al.
European journal of cancer (Oxford, England : 1990), 32A(3), 506-511 (1996-03-01)
Hexadecylphosphocholine (HePC, Miltefosine) is a representative of the group of alkyl-lysophosphocholines showing remarkable antitumoral activity in in vitro experiments and in experimental animal tumour models. The epidermoid tumour cell line KB, which is highly sensitive to HePC (half-maximal growth inhibiting
N Grosman
Immunopharmacology, 40(2), 163-171 (1998-11-24)
The influence of selected inhibitors of calcium signalling on the plasma membrane Ca2+-ATPase activity of rat synaptosomes and peritoneal leukocyte membranes was studied. The calmodulin inhibitor calmidazolium was an efficient inhibitor (50%) of the synaptosomal Ca2+-ATPase activity in a manner
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