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31375

Sigma-Aldrich

Dexamethasone

tested according to Ph. Eur.

Synonym(s):

Dexamethasonum, (11β,16α)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione, 9α-Fluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione, 9α-Fluoro-16α-methylprednisolone, Prednisolone F

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About This Item

Empirical Formula (Hill Notation):
C22H29FO5
CAS Number:
50-02-2
Molecular Weight:
392.46
Beilstein/REAXYS Number:
2066651
EC Number:
200-003-9
MDL number:
MFCD00064136
UNSPSC Code:
41116107
PubChem Substance ID:
329753755
NACRES:
NA.21

agency

USP/NF
tested according to Ph. Eur.

Quality Level

100

assay

99.6%

form

solid

mp

262-264 °C (lit.)

solubility

water: soluble 10mg/100 ml at 25 °C
acetone: very slightly soluble
alcohol: very slightly soluble
chloroform: slightly soluble
diethyl ether: very slightly soluble
dioxane: very slightly soluble
methanol: very slightly soluble

application(s)

pharmaceutical (small molecule)

SMILES string

C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO

InChI

1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1

InChI key

UREBDLICKHMUKA-CXSFZGCWSA-N

Gene Information

human ... ABCB1(5243) , CYP3A4(1576) , IL4(3565) , IL5(3567) , NR3C1(2908)
mouse ... Abcb1a(18671) , Abcb1b(18669) , Ifng(15978) , Nos2(18126) , Ptgs2(19225) , Tnf(21926)
rat ... Ar(24208) , Nr3c1(24413) , Tnf(24835)

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Application

Dexamethasone has been used as a DMEM medium supplement utilized in osteogenesis. It has also been used as an alpha-MEM medium supplement to initiate adipogenic differentiation. Additionally, it has also been used to study apoptosis, cell signaling pathways and gene expression.

Biochem/physiol Actions

Dexamethasone is a glucocorticoid anti-inflammatory agent. It regulates T cell survival, growth, and differentiation. Additionally, dexamethasone inhibits the induction of nitric oxide synthase. It induces apoptosis by initiating the initial cleavage of DNA into high molecular weight fragments.
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360FD

Hazard Classifications

Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7233
BCCL2944
BCCK8717
BCCH7096
BCCG4729

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D G Brown et al.
The Journal of biological chemistry, 268(5), 3037-3039 (1993-02-15)
Apoptosis is a major form of cell death, characterized morphologically by chromatin condensation and biochemically by endonuclease cleavage of DNA into oligonucleosomal fragments. Recently, we reported that zinc arrested dexamethasone-induced apoptosis in thymocytes at an early stage, as characterized morphologically
Samad Nadri et al.
The International journal of developmental biology, 51(8), 723-729 (2007-10-17)
Mesenchymal stem cells (MSCs) have been isolated based on the ability of adherence to plastic surfaces. The potential of these cells to differentiate along multiple lineages is the key to identifying stem cell populations in the absence of molecular markers.
Yu-Jen Chang et al.
Stem cells (Dayton, Ohio), 24(3), 679-685 (2005-09-24)
Bone marrow and umbilical cord blood are reported to be the main sources of mesenchymal stem cells (MSCs), which have been proposed for many clinical applications. This study evaluated and quantitated the differentiation potential of bone marrow-derived MSCs (bmMSCs) and
Erich Piovan et al.
Cancer cell, 24(6), 766-776 (2013-12-03)
Glucocorticoid resistance is a major driver of therapeutic failure in T cell acute lymphoblastic leukemia (T-ALL). Here, we identify the AKT1 kinase as a major negative regulator of the NR3C1 glucocorticoid receptor protein activity driving glucocorticoid resistance in T-ALL. Mechanistically
Yukiko Kitase et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 25(12), 2657-2668 (2010-06-26)
Glucocorticoids are known to induce osteocyte apoptosis, whereas mechanical loading has been shown to sustain osteocyte viability. Here we show that mechanical loading in the form of fluid-flow shear stress blocks dexamethasone-induced apoptosis of osteocyte-like cells (MLO-Y4). Prostaglandin E(2) (PGE(2)
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