All Photos(1)
Synonym(s):
1-Hexadecylmercapto-2-methoxymethyl-3-propyl phosphoric acid monocholine ester, BM 41.440
Empirical Formula (Hill Notation):
C26H56NO5PS
CAS Number:
Molecular Weight:
525.77
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Oral
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
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
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
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.
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