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D1756

Sigma-Aldrich

Dexamethasone

≥98% (HPLC), powder

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/REAXYS Number:
2066651
EC Number:
200-003-9
MDL number:
MFCD00064136
UNSPSC Code:
51422306
PubChem Substance ID:
24893536
NACRES:
NA.77

Quality Level

200

assay

≥98% (HPLC)

form

powder

color

off-white

mp

262-264 °C (lit.)

solubility

methanol: 25 mg/mL

originator

Merck & Co., Inc., Kenilworth, NJ, U.S.

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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Application

Dexamethasone has been used:
  • in culture media to induce differentiation of adipose-derived stem cells into osteogenic tissue
  • as a component of adipocyte differentiation medium
  • for in vitro stimulation of primary normal human bronchial epithelial cells (NHBE) and airway smooth muscle (ASM)

Biochem/physiol Actions

Dexamethasone is known to be effective against relapsed multiple myeloma. It is found to decrease inflammation associated with cerebrospinal fluid and central nervous system (CNS) complications, such as hearing loss.
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

Dexamethasone is soluble in DMSO (25 mg/ml), chloroform or ethanol.

Reconstitution

Dilute 1 mg/ml stock solution 1:50 with sterile media and store frozen in working aliquots to avoid repeated freeze-thaw.

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

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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USP

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Dexamethasone

Dexamethasone in adults with bacterial meningitis
De Gans J and Van de BD
The New England Journal of Medicine, 347(20), 1549-1556 (2002)
Increased expression of ADAM33 and ADAM8 with disease progression in asthma
Foley SC, et al.
The Journal of Allergy and Clinical Immunology, 119(4), 863-871 (2007)
Canine adipose-derived-mesenchymal stem cells do not lose stem features after a long-term cryopreservation
Martinello T, et al.
Research in Veterinary Science, 91(1), 18-24 (2011)
Yanan Wu et al.
Polymers, 11(5) (2019-05-11)
Many studies about fabricating organic-inorganic composite materials have been carried out in order to mimic the natural structure of bone. Pearl, which has a special block-and-mortar hierarchical structure, is a superior bone repair material with high osteogenic activity, but it
Magdalena Pasarica et al.
Stem cells (Dayton, Ohio), 26(4), 969-978 (2008-01-22)
Human adenovirus Ad-36 is causatively and correlatively linked with animal and human obesity, respectively. Ad-36 enhances differentiation of rodent preadipocytes, but its effect on adipogenesis in humans is unknown. To indirectly assess the role of Ad-36-induced adipogenesis in human obesity
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