LIPID MAPS

Structure Database (LMSD)

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Common Name

Dexamethasone

Systematic Name

9α-Fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione

Synonyms

16-alpha-Methyl-9-alpha-fluoro-delta1-hydrocortisone

LM ID

LMST02030339

Formula

C₂₂H₂₉O₅F

Exact Mass

Calculate m/z

392.199904

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View spectra on LIPID MAPS Standard Spectra DB

Classification

Biological Context

Dexamethasone is a synthetic glucocorticoid that binds the human glucocorticoid receptor with a higher affinity than a natural ligand, cortisol (Kd = 5 nM versus 17 nM, respectively).¹ Through receptor activation, dexamethasone has both transactivating and transrepressing effects on gene expression, producing, in general, anti-inflammatory results.²

This information has been provided by Cayman Chemical

References

1. Mulatero, P., Panarelli, M., Schiavone, D., et al. Impaired cortisol binding to glucocorticoid receptors in hypertensive patients. Hypertension 30(5), 1274-1278 (1997).

2. Beck, I.M., Vanden Berghe, W., Vermeulen, L., et al. Crosstalk in inflammation: The interplay of glucocorticoid receptor-based mechanisms and kinases and phosphatases. Endocr. Rev. 30(7), 830-882 (2009).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

16-METHYLATED STEROIDS. II. 16α-METHYL ANALOGS OF CORTISONE, A NEW GROUP OF ANTI-INFLAMMATORY STEROIDS. 9α-HALO DERIVATIVES,
J Am Chem Soc, 1958

DOI: 10.1021/ja01545a063

String Representations

InChiKey (Click to copy)

UREBDLICKHMUKA-CXSFZGCWSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1CC2[C@](C)(C=CC(=O)C=2)[C@@]2(F)[C@@H](O)C[C@@]3(C)[C@@]([H])(C[C@@H](C)[C@]3(O)C(CO)=O)[C@]12[H]