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46165

Supelco

Dexamethasone

VETRANAL®, analytical standard

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:
41116107
PubChem Substance ID:
329757092
NACRES:
NA.24

grade

analytical standard

Quality Level

100

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

262-264 °C (lit.)

application(s)

clinical

format

neat

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 ... NR3C1(2908)

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General description

Dexamethasone is a synthetic glucocorticoid and cortisol analogue. It is used in the suppression of adrenocorticotropic hormone (ACTH) and cortisol production in normal subjects.

Application

Dexamethasone may be used as a reference standard in the determination of dexamethasone in biological samples using high-performance liquid chromatography (HPLC).
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

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

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Legal Information

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

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H360FD

Hazard Classifications

Repr. 1B

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCD9905
BCCC3569
BCCB2577
BCBZ6032
BCBV7721

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Sigma-Aldrich

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Sigma-Aldrich

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Improved HPLC method for simultaneous analysis of cortisol, 11-deoxycortisol, prednisolone, methylprednisolone, and dexamethasone in serum and urine.
McWhinney CB, et al.
Clinical Chemistry, 42(6), 979-981 (1996)
Tietz Textbook of Clinical Chemistry and Molecular Diagnostics (2012)
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
Yukiko Kitase et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 25(12), 2657-2668 (2010-06-26)
Glucocorticoids are known to induce osteocyte apoptosis, whereas mechanical loading has been shown to sustain osteocyte viability. Here we show that mechanical loading in the form of fluid-flow shear stress blocks dexamethasone-induced apoptosis of osteocyte-like cells (MLO-Y4). Prostaglandin E(2) (PGE(2)
S Choi et al.
British journal of anaesthesia, 112(3), 427-439 (2014-01-15)
Brachial plexus nerve blocks (BPBs) have analgesic and opioid sparing benefits for upper extremity surgery. Single-injection techniques are limited by the pharmacological duration and therapeutic index of local anaesthetics (LAs). Continuous catheter techniques, while effective can present management challenges. Off-label
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