Dexamethasone acetate

CAS# 1177-87-3

Dexamethasone acetate

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Chemical structure

Dexamethasone acetate

3D structure

Chemical Properties of Dexamethasone acetate

Cas No. 1177-87-3 SDF Download SDF
PubChem ID 236702 Appearance Powder
Formula C24H31FO6 M.Wt 434.5
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Dexamethasone 21-acetate
Solubility DMSO : 50 mg/mL (115.07 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name [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] acetate
SMILES CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)COC(=O)C)O)C)O)F)C
Standard InChIKey AKUJBENLRBOFTD-RPRRAYFGSA-N
Standard InChI InChI=1S/C24H31FO6/c1-13-9-18-17-6-5-15-10-16(27)7-8-21(15,3)23(17,25)19(28)11-22(18,4)24(13,30)20(29)12-31-14(2)26/h7-8,10,13,17-19,28,30H,5-6,9,11-12H2,1-4H3/t13-,17+,18+,19+,21+,22+,23+,24+/m1/s1
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.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Dexamethasone acetate

DescriptionDexamethasone acetate is a glucocorticoid receptor agonist.In Vitro:Dexamethasone regulates several transcription factors, including activator protein-1, nuclear factor-AT, and nuclear factor-kB, leading to the activation and repression of key genes involved in the inflammatory response[1]. Dexamethasone potently inhibits granulocyte-macrophage colony stimulating factor (GM-CSF) release from A549 cells with EC50 of 2.2 nM. Dexamethasone (EC50=36 nM) induces transcription of the β2-receptor is found to correlate with glucocorticoid receptor (GR) DNA binding and occurred at 10-100 fold higher concentrations than the inhibition of GM-CSF release. Dexamethasone (IC50=0.5 nM) inhibits a 3×κB (NF-κB, IκBα, and I-κBβ), which is associated with inhibition of GM-CSF release[2].In Vivo:It has previously been reported that treatment with Dexamethasone at a dose of 2×5 mg/kg efficiently inhibits lipopolysaccharide (LPS)-induced inflammation. In our experimental system, treatment with a single dose of Dexamethasone 10 mg/kg (i.p.) significantly decreases recruitment of granulocytes as well as spontaneous production of oxygen radicals compared with animals expose to LPS and injected with solvent alone (saline). The effects are statistically significant when administered both 1 h before and 1 h after inhalation of LPS. The number of granulocytes in BALF decreased to levels comparable to healthy animals (given an aerosol of water)[3]. Rats treated with Dexamethasone consume less food and weighed less than control rats. Treated rats also weigh less than pair-fed animals though their food intake is similar. Five days of Dexamethasone injection result in a significant increase in both the liver mass (+42%) and the liver to body weight ratio (+65%). The wet weight of gastrocnemius muscle decreases 20% after 5 days of treatment, but it remains unaffected relative to body weight (g/100 g body weight), indicating that muscle weight loss paralleled body weight loss[4].

References:
[1]. LaLone CA, et al. Effects of a glucocorticoid receptor agonist, Dexamethasone, on fathead minnow reproduction, growth, and development. Environ Toxicol Chem. 2012 Mar;31(3):611-22. [2]. Adcock IM, et al. Ligand-induced differentiation of glucocorticoid receptor (GR) trans-repression and transactivation: preferential targetting of NF-kappaB and lack of I-kappaB involvement. Br J Pharmacol. 1999 Jun;127(4):1003-11 [3]. Rocksén D, et al. Differential anti-inflammatory and anti-oxidative effects of Dexamethasone and N-acetylcysteine in endotoxin-induced lung inflammation. Clin Exp Immunol. 2000 Nov;122(2):249-56 [4]. Roussel D, et al. Dexamethasone treatment specifically increases the basal proton conductance of rat liver mitochondria. FEBS Lett. 2003 Apr 24;541(1-3):75-9.

Protocol

Animal Administration [3][4]
Mice[3] Female C57Bl/6JBom mice (age 10-12 weeks) are used in all experiments. Dexamethasone is administered as a single injection of 1 or 10 mg/kg. Dexamethasone is dissolved in saline and 400 μL are injected intraperitoneally, either 1 h before or 1 h after LPS exposure. In one experiment, N-acetylcysteine (NAC) (100 and 500 mg/kg) is injected successively every 4•5 h, starting 1 h before challenge (five injections in total). A control group of LPS-exposed animals are injected intraperitoneally with solvent alone (saline). Intratracheal administration is performed by instillation of 100 μL NAC (50, 100 or 500 mg/kg) or Dexamethasone (10 mg/kg) into the lungs of mice anaesthetized with 15 mg/kg Rapinovet (i.v.). Rats[4] Male Sprague-Dawley rats are used.Dexamethasone-treated rats are injected intraperitoneally once daily with Dexamethasone (1.5 mg/kg body weight) for 5 days and are allowed to feed ad libitum. The Dexamethasone dose (1.5 mg/kg/day) and the duration of treatment (5 days) are specifically chosen as this treatment induced a reproducible and marked catabolic state. Control rats received no treatment and are fed ad libitum. In order to take into account the decrease in food intake induced by Dexamethasone treatment, a third group of pair-fed rats are used. These rats are provided with the same amount of food as Dexamethasone-injected rats and are treated with a daily isovolumic intraperitoneal injection of NaCl (0.9%) for 5 days. After the final injection of Dexamethasone or NaCl, the animals are fasted overnight prior to being killed by decapitation.

References:
[1]. LaLone CA, et al. Effects of a glucocorticoid receptor agonist, Dexamethasone, on fathead minnow reproduction, growth, and development. Environ Toxicol Chem. 2012 Mar;31(3):611-22. [2]. Adcock IM, et al. Ligand-induced differentiation of glucocorticoid receptor (GR) trans-repression and transactivation: preferential targetting of NF-kappaB and lack of I-kappaB involvement. Br J Pharmacol. 1999 Jun;127(4):1003-11 [3]. Rocksén D, et al. Differential anti-inflammatory and anti-oxidative effects of Dexamethasone and N-acetylcysteine in endotoxin-induced lung inflammation. Clin Exp Immunol. 2000 Nov;122(2):249-56 [4]. Roussel D, et al. Dexamethasone treatment specifically increases the basal proton conductance of rat liver mitochondria. FEBS Lett. 2003 Apr 24;541(1-3):75-9.

Dexamethasone acetate Dilution Calculator

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Dexamethasone acetate Molarity Calculator

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Preparing Stock Solutions of Dexamethasone acetate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.3015 mL 11.5075 mL 23.015 mL 46.0299 mL 57.5374 mL
5 mM 0.4603 mL 2.3015 mL 4.603 mL 9.206 mL 11.5075 mL
10 mM 0.2301 mL 1.1507 mL 2.3015 mL 4.603 mL 5.7537 mL
50 mM 0.046 mL 0.2301 mL 0.4603 mL 0.9206 mL 1.1507 mL
100 mM 0.023 mL 0.1151 mL 0.2301 mL 0.4603 mL 0.5754 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Dexamethasone acetate

Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid drugs that has anti-inflammatory and immunosuppressant properties.

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References on Dexamethasone acetate

Mucoadhesive dexamethasone acetate-polymyxin B sulfate cationic ocular nanoemulsion--novel combinatorial formulation concept.[Pubmed:27455551]

Pharmazie. 2016 Jun;71(6):327-33.

Dexamethasone acetate (DEX) and polymyxin B sulfate (polymyxin B) were formulated as a cationic nanoemulsion for the treatment of ophthalmic infections. As novel concept, the positive charge to achieve mucoadhesion was not generated by toxicologically and regulatorily problematic cationic lipids or polymers, but by using a positively charged drug in combination with positively charged preservatives. The preservative also acts as co-surfactant to stabilize the emulsion. Nanoemulsions with the lipid phase Eutanol G-Lipoid S 100 (70%:30%) containing 0.05% (w/w) DEX were produced by high pressure homogenization, followed by dissolving the hydrophilic molecules in the water phase, e.g. polymyxin B (0.1%, w/w), cetylpyridinium chloride (0.01%, w/w) and glycerol (2.6%, w/w) to yield a combination product. The particles were below 200 nm with narrow size distribution. The osmolality (374 mOsm/kg), pH (5.31) and viscosity (2.45 mPa s at 37 degrees C) were compatible to the ocular administration. The zeta potential of the optimized formulation was shifted from approx. +9 mV to -11 mV after mucin incubation. The in vitro test revealed no potential cytotoxicity. The final products were stable after 180 days of storage at 4 degrees C and room temperature. The developed product is a viable alternative to the commercial ophthalmic suspensions. Moreover, this concept of generating the positive charge by cationic drug and/or preservative addition can be transferred to other ophthalmic products.

Dexamethasone and acetate modulate cytoplasmic leptin in bovine preadipocytes.[Pubmed:25049989]

Asian-Australas J Anim Sci. 2014 Apr;27(4):567-73.

Hormonal and nutrient signals regulate leptin synthesis and secretion. In rodents, leptin is stored in cytosolic pools of adipocytes. However, not much information is available regarding the regulation of intracellular leptin in ruminants. Recently, we demonstrated that leptin mRNA was expressed in bovine intramuscular preadipocyte cells (BIP cells) and that a cytoplasmic leptin pool may be present in preadipocytes. In the present study, we investigated the expression of cytoplasmic leptin protein in BIP cells during differentiation as well as the effects of various factors added to the differentiation medium on its expression in BIP cells. Leptin mRNA expression was observed only at 6 and 8 days after adipogenic induction, whereas the cytoplasmic leptin concentration was the highest on day 0 and decreased gradually thereafter. Cytoplasmic leptin was detected at 6 and 8 days after adipogenic induction, but not at 4 days after adipogenic induction. The cytoplasmic leptin concentration was reduced in BIP cells at 4 days after treatment with dexamethasone, whereas cytoplasmic leptin was not observed at 8 days after treatment. In contrast, acetate significantly enhanced the cytoplasmic leptin concentration in BIP cells at 8 days after treatment, although acetate alone did not induce adipocyte differentiation in BIP cells. These results suggest that dexamethasone and acetate modulate the cytoplasmic leptin concentration in bovine preadipocytes.

Topical delivery of dexamethasone acetate from hydrogel containing nanostructured liquid carriers and the drug.[Pubmed:25940221]

Arch Pharm Res. 2015 Nov;38(11):1999-2007.

The potential of hydrogel containing nanostructured lipid carriers (NLC) to enhance the skin permeation rate and skin deposition of Dexamethasone acetate (DEA) was investigated. The particle size of obtained NLCs was around 224.4 nm. NLCs had core-shell structure and DEA existed in amorphous state in NLCs. The permeation rate of DEA through excised mouse skins from hydrogel containing DEA-NLC (DEA-NLC-hydrogel) was 7.3 times higher than DEA-ointment. The skin deposition of DEA from DEA-NLC-hydrogel increased 3.8 folds compared to that from solution of DEA in hydrogel (DEA-hydrogel).

Changes of Spleen in Wistar Rats Exposed to Therapeutic Doses of Dexamethasone and Medroxyprogesterone Acetate Evaluated by Stereological Parameters.[Pubmed:27442392]

Pril (Makedon Akad Nauk Umet Odd Med Nauki). 2015;36(3):13-25.

The aim of our investigation was to evaluate the immunosuppressive effect of medroxyprogesterone acetate (MPA) determining the volume densities of the structural components of the spleen. The volume densities of the same structural components of spleen were determined after administration of dexamethasone too, in order to see whether the morphological changes induced by MPA are in the same line with the changes caused by dexamethasone. 60 female Wistar rats were divided into 5 groups. The control group of rats was administered physiological solution. The remaining, 4 experimental groups were administered: dexamethasone at a therapeutic daily dose of 0.6 mg/kg bw and maximal therapeutic dose of 3 mg/kg bw, and MPA at a therapeutic dose of 30 mg/kg bw and maximal therapeutic dose of 150 mg/kg bw. The drugs were applied intramuscularly for 7 days. Spleen paraffin sections were stained according to the methods: hematoxylin-eosin, Masson and Elastica van-Gieson. Stereological measurements were performed by using the Weibl's multipurpose test system (M-42). The histological analyses of the structural components of the spleen in rats treated with dexamethasone and MPA have shown reduction of the white pulp and the marginal zone and an apparent decrease of the cellular density of the lymphocyte component of the pulp. The stereological analysis of the spleen showed significant decrease of the splenic pulp volume density and significant increase of the connective tissue volume density. Reducing the presence of splenic pulp was mainly due to the decrease in the volume density of all structural components of the white pulp. Changes were observed in all drug treated groups of rats. Our results have shown that the MPA provoked changes suggested atrophy of the spleen lymphoid tissue. Although the atrophic changes of the spleen were significant after the application of both dexamethasone and MPA, the white pulp was significantly more sensitive substrate for dexamethasone than for the MPA.

Description

Dexamethasone acetate (Dexamethasone 21-acetate) is a glucocorticoid receptor agonist. Dexamethasone acetate has the potential for ophthalmic infections treatment.

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