Safingol

Safingol
Names
Preferred IUPAC name
(2S,3S)-2-Aminooctadecane-1,3-diol
Other names
(−)-threo-Dihydrosphingosine; (2S,3S)-2-Amino-1,3-octadecanediol; L-(−)-threo-Sphinganine; L-threo-Dihydrosphingosine; L-threo-2-Amino-1,3-octadecanediol; threo-1,3-Dihydroxy-2-aminooctadecane
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18-/m0/s1 N
    Key: OTKJDMGTUTTYMP-ROUUACIJSA-N N
  • InChI=1/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18-/m0/s1
    Key: OTKJDMGTUTTYMP-ROUUACIJBJ
  • OC[C@H](N)[C@@H](O)CCCCCCCCCCCCCCC
Properties
C18H39NO2
Molar mass 301.515 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Safingol is a lyso-sphingolipid protein kinase inhibitor. It has the molecular formula C18H39NO2 and is a colorless solid. Medicinally, safingol has demonstrated promising anticancer potential as a modulator of multi-drug resistance and as an inducer of necrosis. The administration of safingol alone has not been shown to exert a significant effect on tumor cell growth. However, preclinical and clinical studies have shown that combining safingol with conventional chemotherapy agents such as fenretinide, vinblastine, irinotecan and mitomycin C can dramatically potentiate their antitumor effects. In phase I clinical trials, it was found to be safe to co-administer with cisplatin, but caused reversible dose-dependent hepatotoxicity.

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