Synonym
XM462; XM 462; XM-462;
IUPAC/Chemical Name
N-((2S,3S)-1,3-dihydroxy-4-(tridecylthio)butan-2-yl)octanamide
InChi Key
FOIBJHCOSKEGLA-BJKOFHAPSA-N
InChi Code
InChI=1S/C25H51NO3S/c1-3-5-7-9-10-11-12-13-14-16-18-20-30-22-24(28)23(21-27)26-25(29)19-17-15-8-6-4-2/h23-24,27-28H,3-22H2,1-2H3,(H,26,29)/t23-,24+/m0/s1
SMILES Code
CCCCCCCC(N[C@H]([C@H](O)CSCCCCCCCCCCCCC)CO)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
445.75
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Ordóñez-Gutiérrez L, Benito-Cuesta I, Abad JL, Casas J, Fábrias G, Wandosell F. Dihydroceramide Desaturase 1 Inhibitors Reduce Amyloid-β Levels in Primary Neurons from an Alzheimer's Disease Transgenic Model. Pharm Res. 2018 Feb 6;35(3):49. doi: 10.1007/s11095-017-2312-2. PMID: 29411122.
2: Zulueta A, Caretti A, Campisi GM, Brizzolari A, Abad JL, Paroni R, Signorelli P, Ghidoni R. Inhibitors of ceramide de novo biosynthesis rescue damages induced by cigarette smoke in airways epithelia. Naunyn Schmiedebergs Arch Pharmacol. 2017 Jul;390(7):753-759. doi: 10.1007/s00210-017-1375-2. Epub 2017 Apr 13. PMID: 28409208.
3: Gagliostro V, Casas J, Caretti A, Abad JL, Tagliavacca L, Ghidoni R, Fabrias G, Signorelli P. Dihydroceramide delays cell cycle G1/S transition via activation of ER stress and induction of autophagy. Int J Biochem Cell Biol. 2012 Dec;44(12):2135-43. doi: 10.1016/j.biocel.2012.08.025. Epub 2012 Sep 7. PMID: 22960157.
4: Camacho L, Simbari F, Garrido M, Abad JL, Casas J, Delgado A, Fabriàs G. 3-Deoxy-3,4-dehydro analogs of XM462. Preparation and activity on sphingolipid metabolism and cell fate. Bioorg Med Chem. 2012 May 15;20(10):3173-9. doi: 10.1016/j.bmc.2012.03.073. Epub 2012 Apr 6. PMID: 22537678.
5: Munoz-Olaya JM, Matabosch X, Bedia C, Egido-Gabás M, Casas J, Llebaria A, Delgado A, Fabriàs G. Synthesis and biological activity of a novel inhibitor of dihydroceramide desaturase. ChemMedChem. 2008 Jun;3(6):946-53. doi: 10.1002/cmdc.200700325. PMID: 18236489.
