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D9184

Sigma-Aldrich

Dexamethasone

meets USP testing specifications

Synonym(s):

(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:
2066651
EC Number:
200-003-9
MDL number:
MFCD00064136
UNSPSC Code:
12352212
PubChem Substance ID:
24894273
NACRES:
NA.21

biological source

synthetic (organic)

Quality Level

200

Agency

USP/NF
meets USP testing specifications

Assay

97.0-102.0%

form

solid

mp

262-264 °C (lit.)

shipped in

ambient

storage temp.

2-8°C

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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General description

Dexamethasone is an anti-inflammatory glucocorticoid with a range of effects on cell survival, cell signaling and gene expression. It is useful for study of apoptosis, cell signaling pathways and gene expression.

Application

Dexamethasone was used as medium supplement in the following studies:
  • To investigate the osteogenic differentiation and chondrogenic differentiation of bone marrow mesenchymal stem cells (MSCs).
  • In α-MEM (minimum essential medium) for inducing the osteogenic and adipogenic differentiation in mesenchymal stem cells from human bone marrow and umbilical cord blood.
  • For the isolation and characterization of mesenchymal stem cells isolated from 6- to 8-week-old C57BL/6J mice.

Biochem/physiol Actions

Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Laura Pierdomenico et al.
Transplantation, 80(6), 836-842 (2005-10-08)
Bone marrow mesenchymal stem cells (MSCs) are currently being investigated in preclinical and clinical settings because of their multipotent differentiative capacity or, alternatively, their immunosuppressive function. The aim of this study was to evaluate dental pulp (DP) as a potential
Ezio Gerdoni et al.
Annals of neurology, 61(3), 219-227 (2007-03-28)
To evaluate the ability of mesenchymal stem cells (MSCs), a subset of adult stem cells from bone marrow, to cure experimental autoimmune encephalomyelitis. The outcome of the injection of MSCs, in mice immunized with the peptide 139-151 of the proteolipid
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
Michael J White et al.
Cell, 159(7), 1549-1562 (2014-12-20)
Activated caspases are a hallmark of apoptosis induced by the intrinsic pathway, but they are dispensable for cell death and the apoptotic clearance of cells in vivo. This has led to the suggestion that caspases are activated not just to kill
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