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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:
Molecular Weight:
525.77
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
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

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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S L Croft et al.
The Journal of antimicrobial chemotherapy, 38(6), 1041-1047 (1996-12-01)
The in-vitro activities of four anticancer alkyllysophospholipids, ET-18-OCH3 (edelfosine), hexadecylphosphocholine (miltefosine), ilmofosine and SRI 62-834, were determined with ED50 values for Leishmania donovani and Trypanosoma cruzi amastigotes between 0.2 and 5.0 microM and for Trypanosoma brucei trypomastigotes between 7.0 and
Samira Azzouz et al.
Basic & clinical pharmacology & toxicology, 96(1), 60-65 (2005-01-26)
The anti-proliferative action of three alkyl-lysophospholipid derivatives, edelfosine (ET-OCH), miltefosine (Hexadecylphosphocholine), and ilmofosine (BM 14.440) has been studied on the promastigotes and amastigotes of Leishmania donovani. The effect of the three drugs has previously been studied, but the action mode
S L Croft et al.
Transactions of the Royal Society of Tropical Medicine and Hygiene, 87(2), 217-219 (1993-03-01)
The ether phospholipid ilmofosine (BM 41.440) was active in vitro against amastigotes of Leishmania donovani and an antimony-resistant line of L. infantum in mouse peritoneal macrophages with ED50 values of 3.7 microM and 3.5 microM respectively. Ilmofosine was also active
L L Trulla et al.
Lipids, 28(5), 403-406 (1993-05-01)
Ether lipids are defined here as analogues of naturally occurring lysophosphatidylcholines with cytotoxic activity against neoplastic cells. The activity of 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine (ET18OMe) and 3-hexadecylmercapto-2-methoxymethyl-propyl-1-phosphocholine (Ilmofosine) (BM 41.440) was tested in variants of B16 murine melanoma, grown in adhesion cultures (B16F1
J Hofmann et al.
Biochemical and biophysical research communications, 199(2), 937-943 (1994-03-15)
The thioether phospholipid derivative ilmofosine (BM41440), a selective inhibitor of protein kinase C, is a new anticancer drug presently undergoing Phase II clinical trials. We have examined the influence of the compound on cell cycle progression. Ilmofosine was found to

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