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D1756

Sigma-Aldrich

Dexamethasone

≥98% (HPLC), powder

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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
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:
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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General description

Dexamethasone is a potent glucocorticoid with minimal to no mineralocorticoid activity. Dexamethasone exhibits pleiotropic effects on multiple signaling pathways, some of its functions include, inhibition of neutrophil migration and reduction of lymphocyte colony proliferation. Research findings show, dexamethasone might prevent high-altitude pulmonary edema by decreasing pulmonary artery pressure.

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

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product D1756, Dexamethasone, soluble in?

    Dexamethasone is practically insoluble in water. It is soluble in ethanol, methanol, acetone, dioxane, and slightly soluble in chloroform. Sigma routinely tests the solubility at 50 mg/mL in ethanol with heat, yielding a clear, colorless to faint yellow solution. However, dexamethasone will precipitate out of solution as the temperature returns to room temperature. At 25 mg/mL in methanol or ethanol, a clear colorless solution is obtained without heating.  The solubility of dexamethasone in DMSO is 606 mg/mL at 25°C.

  4. What is the solution stability of Product D1756, Dexamethasone?

    Aqueous solutions of dexamethasone are stable for at least 30 days at 4°C. A stock solution at a concentration of 1mg/mL in absolute ethanol can be diluted 1:50 with sterile media and stored frozen as working aliquots.

  5. Is Product D1756, Dexamethasone, suitable for cell culture?

    This product has not been tested for cell culture. Please consider either Product No. D8893 or D4902, both of which are cell culture tested.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
Dexamethasone induction of a heat stress response
Guerrero JA, et al.
Methods in Enzymology (2011)
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
Dexamethasone in adults with bacterial meningitis
De Gans J and Van de BD
The New England Journal of Medicine, 347(20), 1549-1556 (2002)
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