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Dexamethasone palmitate

Catalog No.GC38573

Dexamethasone palmitate Chemical Structure

Dexamethasone palmitate (DXP), a lipophilic prodrug of Dexamethasone (DXM), is a glucocorticoid receptor agonist with a 47-fold lower affinity for the glucocorticoid receptor than DXM.

Size Price Stock Qty
10mM*1mL in DMSO
$135.00
In stock
5mg
$98.00
In stock
10mg
$163.00
In stock
50mg
$347.00
In stock
100mg
$591.00
In stock

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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Protocol

Cell experiment [1]:

Cell lines

RAW 264.7 cells

Preparation Method

After 24 h of incubation with 100 μg/mL Dexamethasone palmitate, cell supernatants were collected and frozen at 20 C until analysis was performed. Cells were detached and counted.

Reaction Conditions

100 μg/mL Dexamethasone palmitate,24h

Applications

A decrease of cytokines concentration was clearly observed resulting from the anti-inflammatory effect of Dexamethasone palmitate-NPs.

Animal experiment [2]:

Animal models

Brown Norway male rats

Preparation Method

Choroidal neovascularization (CNV) was induced with a 532-nm argon laser photocoagulator in the right eyes of the anesthetized animals. Following the laser procedure on day 0 supratemporal IVT injections of either the vehicle [phosphate- buffered saline (PBS); 0.8% Dexamethasone palmitate emulsion (4 μg Dexamethasone palmitate; 0.5 μL), and Kenacort were administered to the treated right eyes.

Dosage form

4 μg Dexamethasone palmitate;0.5 μL

Applications

Rat efficacy data demonstrated that IVT administration of Dexamethasone palmitate emulsions is effective for delivering therapeutic concentrations of DXM at the level of the choroid.

References:

[1]. Romero IA, Radewicz K, et,al. Changes in cytoskeletal and tight junctional proteins correlate with decreased permeability induced by dexamethasone in cultured rat brain endothelial cells. Neurosci Lett. 2003 Jun 26;344(2):112-6. doi: 10.1016/s0304-3940(03)00348-3. PMID: 12782340.

[2]. Daull P, Paterson CA, et,al. A preliminary evaluation of dexamethasone palmitate emulsion: a novel intravitreal sustained delivery of corticosteroid for treatment of macular edema. J Ocul Pharmacol Ther. 2013 Mar;29(2):258-69. doi: 10.1089/jop.2012.0044. Epub 2013 Jan 18. PMID: 23331052.

Background

Dexamethasone palmitate (DXP), a lipophilic prodrug of Dexamethasone (DXM), is a glucocorticoid receptor agonist with a 47-fold lower affinity for the glucocorticoid receptor than DXM[1].

A decrease of cytokines concentration was clearly observed resulting from the anti-inflammatory effect of Dexamethasone palmitate-NPs .the MCP-1 chemokine was strongly and significantly reduced by Dexamethasone palmitate-NPs and TNFα in presence of LPS[2].

Rat efficacy data demonstrated that IVT administration of Dexamethasone palmitate emulsions is effective for delivering therapeutic concentrations of DXM at the level of the choroid[2]. Dexamethasone palmitate-NPs could benefit from the typical high vascular permeability of inflamed joints and diffuse passively to accumulate and be retained in the diseased sites. This accumulation in inflamed joints led to improvement of the joint inflammation and eventually disease remission[3].

References:
[1]:Romero IA, Radewicz K, Jubin E, Michel CC, Greenwood J, Couraud PO, Adamson P. Changes in cytoskeletal and tight junctional proteins correlate with decreased permeability induced by dexamethasone in cultured rat brain endothelial cells. Neurosci Lett. 2003 Jun 26;344(2):112-6. doi: 10.1016/s0304-3940(03)00348-3. PMID: 12782340.
[2]: Daull P, Paterson CA, Kuppermann BD, Garrigue JS. A preliminary evaluation of dexamethasone palmitate emulsion: a novel intravitreal sustained delivery of corticosteroid for treatment of macular edema. J Ocul Pharmacol Ther. 2013 Mar;29(2):258-69. doi: 10.1089/jop.2012.0044. Epub 2013 Jan 18. PMID: 23331052.
[3]: Lorscheider M, Tsapis N, Ur-Rehman M, Gaudin F, Stolfa I, Abreu S, Mura S, Chaminade P, Espeli M, Fattal E. Dexamethasone palmitate nanoparticles: An efficient treatment for rheumatoid arthritis. J Control Release. 2019 Feb 28;296:179-189. doi: 10.1016/j.jconrel.2019.01.015. Epub 2019 Jan 16. PMID: 30659904.

Chemical Properties

Cas No. 14899-36-6 SDF
Synonyms N/A
Chemical Name N/A
Canonical SMILES C[C@@]12[C@](C[C@@H](C)[C@]2(O)C(COC(CCCCCCCCCCCCCCC)=O)=O)([H])[C@@]3([H])[C@@](F)([C@@]4(C(CC3)=CC(C=C4)=O)C)[C@@H](O)C1
Formula C38H59FO6 M.Wt 630.87
Solubility DMSO: 250 mg/mL (396.28 mM) Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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Research Update

Dexamethasone palmitate nanoparticles: An efficient treatment for rheumatoid arthritis

J Control Release2019 Feb 28;296:179-189.PMID: 30659904DOI: 10.1016/j.jconrel.2019.01.015

Rheumatoid arthritis (RA) is a prevalent autoimmune disease characterized by joint inflammation, bone and cartilage erosion. The use of glucocorticoids in the treatment of RA is hampered by significant side effects induced by their unfavorable pharmacokinetics. Delivering glucocorticoids by means of nanotechnologies is promising but the encapsulation of highly crystalline and poorly water-soluble drugs results in poor loading and low stability. We report here the design of 130 nm nanoparticles made of solely dexamethasone palmitate, stabilized by polyethylene glycol-linked phospholipids displaying a negative zeta potential (-55 mV), high entrapment efficiency and stability over 21 days under storage at 4 °C. X ray diffraction showed no crystallization of the drug. When incubated in serum, nanoparticles released free dexamethasone which explains the in vitro anti-inflammatory effect on LPS-activated RAW 264.7 macrophages. Moreover, we demonstrate in a murine collagen-induced arthritis model the improved therapeutic efficacy of these nanoparticles. Their passive accumulation in arthritic joints leads to disease remission and recovery of the joint structure at a dose of 1 mg/kg dexamethasone, without any adverse effects. Dexamethasone palmitate nanoparticles are promising in the treatment of inflammation in rheumatoid arthritis with a very significant difference occurring at the late stage of inflammation allowing to prevent the progression of the disease.

Tiny dexamethasone palmitate nanoparticles for intravitreal injection: Optimization and in vivo evaluation

Int J Pharm2021 May 1;600:120509.PMID: 33766637DOI: 10.1016/j.ijpharm.2021.120509

Tiny nanoparticles of dexamethasone palmitate (DXP) were designed as transparent suspensions for intravitreal administration to treat age-related macular degeneration (AMD). The influence of three surfactants (PEG-40-stearate and Pluronic block copolymers F68 and F127) on nanoparticles size and stability was investigated and led to an optimal formulation based on Pluronic F127 stabilizing DXP nanoparticles. Size measurements and TEM revealed tiny nanoparticles (around 35 nm) with a low opacity, compatible with further intravitreal injection. X-Ray powder diffraction (XRPD) and transmission electronic microscopy (TEM) performed on freeze-dried samples showed that DXP nanoparticles were rather monodisperse and amorphous. The efficacy of DXP nanoparticles was assessed in vivo on pigmented rabbits with unilateral intravitreal injections. After breakdown of the blood-retinal barrier (BRB) induced by injection of rhVEGF165 with carrier protein, DXP nanoparticles induced a restoration of the BRB 1 month after their intravitreal injection. However, their efficacy was limited in time most probably by clearance of DXP nanoparticles after 2 months due to their small size.

Nanomedicine-based combination of dexamethasone palmitate and MCL-1 siRNA for synergistic therapeutic efficacy against rheumatoid arthritis

Drug Deliv Transl Res2021 Dec;11(6):2520-2529.PMID: 34331261DOI: 10.1007/s13346-021-01037-x

The main aim of this research was to design a MCL-1 siRNA and dexamethasone (DEX)-loaded folate modified poly(lactide-co-glycolide) (PLGA)-based polymeric micelles with an eventual goal to improve the therapeutic outcome in the rheumatoid arthritis (RA). Polymeric micelles encapsulating the MCL-1 siRNA and DEX was successfully developed and observed to be stable. Physicochemical characteristics such as particle size and particle morphology were ideal for the systemic administration. Folate-conjugated DEX/siRNA-loaded polymeric micelles (DS-FPM) significantly lowered the MCL-1 mRNA expression compared to either DEX/siRNA-loaded polymeric micelles (DS-PM) or free siRNA in Raw264.7 cells and macrophage cells suggesting the importance of targeted nanocarriers. Most importantly, DS-FPM exhibited a greatest decrease in the hind paw volume with lowest clinical score compared to any other treated group indicating a superior anti-inflammatory activity. DS-FPM showed significantly lower levels of the TNF-α and IL-1β compared to AIA model and free groups. The folate receptor (FR)-targeting property of DS-FPM has been demonstrated to be a promising delivery platform for the effective delivery of combination therapeutics (siRNA and DEX) toward the treatment of rheumatoid arthritis.

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