Dexamethasone

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Structural formula
Structure of dexamethasone
General
Non-proprietary name Dexamethasone
other names
  • 9-fluoro-11 β , 17,21-trihydroxy-16 α -methyl-pregna-1,4-diene-3,20-dione ( IUPAC )
  • Dexamethasonum ( Latin )
  • Oradexon
Molecular formula C 22 H 29 FO 5
Brief description

colorless crystals

External identifiers / databases
CAS number 50-02-2
EC number 200-003-9
ECHA InfoCard 100,000,004
PubChem 5743
DrugBank DB01234
Wikidata Q422252
Drug information
ATC code

A01 AC02 , C05 AA09 , D07 AB19 , D07 XB05 , D10 AA03 , H02 AB02 , R01 AD03 , S01 BA01 , S01 CB01 , S02 BA06 , S03 BA01

Drug class

Glucocorticoids

properties
Molar mass 392.47 g · mol -1
Physical state

firmly

Melting point

262-264 ° C

solubility
  • practically insoluble in water (89 mg l −1 at 25 ° C)
  • soluble in ethanol and chloroform
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
08 - Dangerous to health

danger

H and P phrases H: 360D
P: 201-280-308 + 313
Toxicological data

54 mg kg −1 ( LD 50 ,  rat ,  ip )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dexamethasone (9-fluoro-16 α- methyl prednisolone ) is an artificial glucocorticoid that has anti-inflammatory and depressant effects on the immune system . It is one of the long-acting glucocorticoids and is around 25 times stronger than the body's own products and has no relevant mineral corticoid effect. It differs from betamethasone only in the position of the methyl group at position 16.

The dexamethasone test (also known as the dexamethasone suppression test ) is carried out with dexamethasone to determine increased serum concentrations of cortisol . A distinction is made between a short-term test with a single dose of dexamethasone and a long-term test with a dexamethasone dose over four days. Dexamethasone decreases the amount of cortisol produced because it targets the same feedback receptors as cortisol. In this way, pathological amounts can be determined. In contrast to other synthetic steroid hormones, dexamethasone does not falsify the laboratory cortisol determination.

application areas

Areas of application include a. inflammatory diseases of the skin ( eczema ) and joints ( arthritis ), brain edema caused by brain tumors and the palliative therapy of malignant tumors ; dexamethasone is also used to prevent and treat vomiting under cytostatics . It is also used in eye drops, e.g. B. after cataract operations .

As with other active ingredients from the group of artificial glucocorticoids, dexamethasone can lead to bone loss; other possible side effects include a. High blood pressure as well as a reduction in muscle mass and a tendency to store fat in the abdomen (see also glucocorticoids # side effects ).

COVID-19

A study by researchers at the University of Oxford has provided evidence that dexamethasone significantly lowers the death rate of intensive care patients suffering from COVID-19 . For patients on ventilators, the death rate fell from 40% to 28%, for patients with oxygen supply from 25% to 20%. The remedy does not fight the virus itself, but slows down the immune system's excessive reaction, the cytokine storm , which is often in severe cases . Treatment with dexamethasone had no beneficial effect in patients who did not need oxygen. The British Minister of Health announced in mid-June 2020 that dexamethasone had been placed on the list of standard procedures against Covid-19 in the UK.

Trade names

Monopreparations

Afpred-Dexa (D), Axidexa (D), Cortidexason (D), Dexabene (D, A), Dexabeta injekt (D), Dexacortin (CH), Dexaflam injekt (D), Dexafluid eye drops (D), Dexafree (CH ), Dexaloscon (D), Fortecortin (D, A, CH), InfectoDexaKrupp (D), Isopto-Dex (D), Lipotalon (D), Maxidex (CH), Mephameson (CH), Monodex (D, A), Solupen (D), Solutio Cordes Dexa (D), Spersadex (D, CH), Totocortin (D), Tuttozem (D)

Combination preparations

Corti Biciron (D), Cortidexason comp. (D), Dexa Biciron (D), Dexa-Gentamicin (D), Dexagent (D), Dexalocal (CH), Dexasalyl (CH), Dispadex (D), Doxyproct (CH), Frakidex (CH), Isopto-Max (D), Maxitrol (CH), Multodrin (A), Nystalocal (D, CH), Otobacid (D), Pigmanorm (CH), Polydexa (CH), Rheumesser (A), Sebo-Psor (CH), Spersadex comp . (CH), Supertendin (D), Terracortril (D), Tobradex (D, A, CH), Uromont (A), as well as numerous generic products for both mono- and combination preparations .

Individual evidence

  1. ↑ a b Entry on dexamethasone. In: Römpp Online . Georg Thieme Verlag, accessed on May 2, 2014.
  2. ↑ a b c data sheet dexamethasone from Sigma-Aldrich , accessed on May 28, 2017 ( PDF ).
  3. ↑ a b Entry on dexamethasone in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ a b Klemens Marischler - 'BASICS Endokrinologie', Elsevier Verlag.
  5. ^ Hyun-Ju Kim et al .: Glucocorticoids suppress bone formation via the osteoclast. In: The Journal of Clinical Investigation. Volume 116, No. 8, 2006, pp. 2152-2160, doi: 10.1172 / JCI28084 Anti-
    inflammatory agents make bones weak. On: Wissenschaft.de from July 29, 2006
  6. ↑ Low-cost dexamethasone reduces death by up to one third in hospitalized patients with severe respiratory complications of COVID-19. Notice from Oxford University of June 16, 2020.
  7. ↑ WHO celebrates study results on Covid-19 drug as a 'breakthrough'. From: handelsblatt.com of June 17, 2020.
  8. ↑ FAZ.net: Cheap drug proves itself in severe Covid-19 course