Dexamethasone palmitate

• CAS: 14899-36-6
• Catalog Number: ACM14899366
• Category: Main Products
• Molecular Weight: 630.87
• Molecular Formula: C38H59FO6
• Synonyms: Dexamethasone-21-palmitate
• Appearance: White to off-white solid

Case Study

Dexamethasone Palmitate Nanoparticles for Rheumatoid Arthritis

Lorscheider, Mathilde, et al. Journal of Controlled Release, 2019, 296, 179-189.

This work reported the design of a 130 nm nanoparticle made solely of dexamethasone palmitate (DXP) stabilized by polyethylene glycol-linked phospholipids. The nanoparticles (NPs) released free dexamethasone and exhibited an in vitro anti-inflammatory effect on LPS-activated RAW 264.7 macrophages.
Preparation of dexamethasone palmitate nanoparticles
· Nanoparticles were synthesized using an emulsion-evaporation method. Initially, 10 ml of milliQ water was cooled to 4°C. A mixture of 50 mg of DXP and 25 mg of DSPE-PEG2000 was dissolved in 1 ml of chloroform. This organic solution was then injected into the cooled water phase, followed by pre-emulsification through 30 seconds of vortexing and 2 minutes of ultrasonication at 40% amplitude in an ice bath. Afterward, the solvent was evaporated under reduced pressure with a rotary evaporator. Once the solvent had completely evaporated, the suspension was stored at 4°C in the dark.
· To obtain fluorescent nanoparticles, the same procedure was applied, incorporating 4% (mol/mol DSPE-PEG2000) of the hydrophobic dye DID (1,1'-dioctadecyl-3,3,3',3'-tetramethylindodicarbocyanine, 4-chlorobenzenesulfonate salt) into the chloroform phase.

Dexamethasone Palmitate Improves Macrophages-Rich Graft-Versus-Host Disease

Nishiwaki, Satoshi, et al. PloS one, 2014, 9(5), e96252.

In this work, it described how dexamethasone palmitate (DP) ameliorates macrophage-rich graft-versus-host disease (GVHD). Research has found that the higher numbers of macrophages in fatal GVHD are inflammatory and that DP treatment helps to reduce this form of GVHD by suppressing macrophage activity.
· Effects of dexamethasone palmitate on macrophages in vitro
The colourimetric assay determined survival rates of mouse macrophage-like RAW264.7 cells (48 hours) after dexamethasone sodium phosphate (DSP) or dexamethasone palmitate (DP). Both DSP and DP inhibited RAW 264.7 cell proliferation in a dose-dependent manner. The capabilities of DP are significantly higher than that of DSP. Specifically, DP reduced RAW 264.7 cell viability by 75% at a concentration of 10 µM, 25-fold lower than the concentration at which DSP acted similarly. When tested at 25 µM dexamethasone, DP was less toxic to splenic T lymphocytes than DSP. Compared with DSP, DP also significantly reduced CCR2 expression on the surface of primary peritoneal macrophages and RAW 264.7 cells and subsequently reduced the migration of primary macrophages toward CCL2.
· Effect of DP on lethal GVHD in mice
It also investigated whether DP could affect lethal mouse GVHD via many macrophages. DP or DSP was administered at 10 mg/kg of dexamethasone on days 7 and 14. DP significantly reduced clinical GVHD scores compared with DSP. Tissue damage and pathological GVHD scores in the skin and intestine were significantly improved in mice treated with DP. Mice treated with DP also had lower numbers of F4/80 + macrophages. These results indicate that DP can alleviate GVHD in many macrophages by inhibiting inflammatory macrophages.

Custom Q&A

What is the PubChem CID of dexamethasone palmitate?

The PubChem CID of dexamethasone palmitate is 63044.

What is the molecular formula of dexamethasone palmitate?

The molecular formula of dexamethasone palmitate is C38H59FO6.

What is the molecular weight of dexamethasone palmitate?

The molecular weight of dexamethasone palmitate is 630.9 g/mol.

What is the IUPAC name of dexamethasone palmitate?

The IUPAC name of dexamethasone palmitate is [2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] hexadecanoate.

What is the InChI of dexamethasone palmitate?

The InChI of dexamethasone palmitate is InChI=1S/C38H59FO6/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-34(43)45-26-33(42)38(44)27(2)23-31-30-20-19-28-24-29(40)21-22-35(28,3)37(30,39)32(41)25-36(31,38)4/h21-22,24,27,30-32,41,44H,5-20,23,25-26H2,1-4H3/t27-,30+,31+,32+,35+,36+,37+,38+/m1/s1.

What is the InChIKey of dexamethasone palmitate?

The InChIKey of dexamethasone palmitate is WDPYZTKOEFDTCU-WDJQFAPHSA-N.

What is the canonical SMILES of dexamethasone palmitate?

The canonical SMILES of dexamethasone palmitate is CCCCCCCCCCCCCCCC(=O)OCC(=O)C1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)C)O.

What is the CAS number of dexamethasone palmitate?

The CAS number of dexamethasone palmitate is 14899-36-6.

What is the XLogP3 value of dexamethasone palmitate?

The XLogP3 value of dexamethasone palmitate is 9.8.

What is the hydrogen bond donor count of dexamethasone palmitate?

The hydrogen donor count of dexamethasone palmitate is 2.