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265005

Sigma-Aldrich

Dexamethasone

Most active and highly stable glucocorticoid.

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Synonym(s):
Dexamethasone, 9α-Fluoro-16α-methylprednisolone
Empirical Formula (Hill Notation):
C22H29FO5
CAS Number:
50-02-2
Molecular Weight:
392.46
MDL number:
MFCD00064136
UNSPSC Code:
51422306
NACRES:
NA.77

Quality Level

100

Assay

≥99% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

DMSO: 25 mg/mL
chloroform: soluble
ethanol: soluble

shipped in

ambient

storage temp.

2-8°C

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

General description

Most active and highly stable glucocorticoid. Causes a reduction in cyclin A and Cdk2 activity, and inhibition of G1/S transition in osteoblasts. Inhibits the phosphorylation of retinoblastoma (Rb) protein. Inhibits the expression of inducible but not constitutive nitric oxide synthase in vascular endothelial cells (IC50 = 5 nM). Enhances active cation transport in aortic smooth muscle cells by stimulating the Na+ - K+ pump. Induces apoptosis in human thymocytes.
Most active and highly stable glucocorticoid. Inhibits the expression of inducible but not constitutive nitric oxide synthase in vascular endothelial cells (IC50 = 5 nM). Enhances active cation transport in aortic smooth muscle cells by stimulating the Na+-K+ pump. Has anti-inflammatory and antirheumatic properties. Induces apoptosis in human thymocytes. In general, 500-1000 nM of dexamethasone is sufficient to induce apoptosis following a 6 h incubation at 37°C.

Biochem/physiol Actions

Cell permeable: no
Primary Target
Phosphorylation of rb protein
Product does not compete with ATP.
Reversible: no
Target IC50: 5 nM Inhibiting the expression of inducible but not constitutive nitric oxide synthase in vascular endothelial cells

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.

Other Notes

Reil, T.D., et al. 2000. J. Surg. Res.92, 108.
Smith, E., et al. 2000. J.Biol. Chem. 275, 1992.
Petit, P.X., et al. 1995. J. Cell Biol.130, 157.
Stern, N., et al. 1994. Am. J. Hypertens. 7, 146.
Donis, J.A., et al. 1993. Biotechniques15, 786.
Ohoka, Y., et al. 1993. Biochem. Biophys. Res. Commun.197, 916.
Sarin, A., et al. 1993. J. Exp. Med.178, 1693.
Vandewalle, A., et al. 1993. J. Cell Physiol.156, 383.
Nieto, M.A., et al. 1992. Clin. Exp. Immunol.88, 341.
Walsh, D., and Avashia, J. 1992. Cleveland Clin. J. Med. 59, 505.
Warters, R.L. 1992. Cancer Res.52, 883.
Sperber, K., et al. 1991. J. Allergy Clin. Immunol.87, 490.
Radomski, M.W., et al. 1990. Proc. Natl. Acad. Sci. USA 87, 10043.
Bettger, W.J., et al. 1981. Proc. Natl. Acad. Sci. USA78, 5588.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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