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Merck

46165

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
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329757092
EC Number:
200-003-9
Beilstein/REAXYS Number:
2066651
MDL number:
MFCD00064136

Product Name

Dexamethasone, VETRANAL®, analytical standard

InChI key

UREBDLICKHMUKA-CXSFZGCWSA-N

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 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

grade

analytical standard

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

Quality Level

100

Gene Information

human ... NR3C1(2908)

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

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.

Other Notes

Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.

Legal Information

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

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3915
BCCM3914
BCCK6301
BCCD9905
BCCC3569

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Tietz Textbook of Clinical Chemistry and Molecular Diagnostics (2012)
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)
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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