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Dexamethasone

Dexamethasone
Skeletal formula of dexamethasone
Ball-and-stick model of the dexamethasone molecule
Clinical data
Trade namesDecadron, Ozurdex, Dexycu, others
AHFS/Drugs.comMonograph
MedlinePlusa682792
License data
Pregnancy
category
Routes of
administration		By mouth, intravenous, intramuscular, subcutaneous, intraosseous, intravitreal, eye drop
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability80–90%
Protein binding77%
MetabolismLiver
Elimination half-lifebiological half-life: 36 to 54 hours; plasma half-life: 4 to 5 hours[8][9]
ExcretionUrine (65%)
Identifiers
  • (8S,9R,10S,11S,13S,14S,16R,17R)-9-Fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.004 Edit this at Wikidata
Chemical and physical data
FormulaC22H29FO5
Molar mass392.467 g·mol−1
3D model (JSmol)
Melting point262 °C (504 °F)
  • O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]1(C(=CC(=O)C=C1)CC[C@H]4[C@@H]2C[C@H]3C)C)C
  • 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 checkY
  • Key:UREBDLICKHMUKA-CXSFZGCWSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dexamethasone is a fluorinated glucocorticoid medication[10] used to treat rheumatic problems, a number of skin diseases, severe allergies, asthma, chronic obstructive pulmonary disease (COPD), croup, brain swelling, eye pain following eye surgery, superior vena cava syndrome (a complication of some forms of cancer),[11] and along with antibiotics in tuberculosis.[10] In adrenocortical insufficiency, it may be used in combination with a mineralocorticoid medication such as fludrocortisone.[10] In preterm labor, it may be used to improve outcomes in the baby.[10] It may be given by mouth, as an injection into a muscle, as an injection into a vein, as a topical cream or ointment for the skin or as a topical ophthalmic solution to the eye.[10] The effects of dexamethasone are frequently seen within a day and last for about three days.[10]

The long-term use of dexamethasone may result in thrush, bone loss, cataracts, easy bruising, or muscle weakness.[10] It is in pregnancy category C in the United States, meaning that it should only be used when the benefits are predicted to be greater than the risks.[1] In Australia, the oral use is category A, meaning it has been frequently used in pregnancy and not been found to cause problems to the baby.[12] It should not be taken when breastfeeding.[10] Dexamethasone has anti-inflammatory and immunosuppressant effects.[10]

Dexamethasone was first synthesized in 1957 by Philip Showalter Hench and was approved for medical use in 1958.[13][14][15] It is on the World Health Organization's List of Essential Medicines.[16] In 2022, it was the 234th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[17][18] It is available as a generic medication.[19] In 2022, the combination of dexamethasone with neomycin and polymyxin B was the 274th most commonly prescribed medication in the United States, with more than 800,000 prescriptions.[20][21]

  1. ^ a b "Dexamethasone Use During Pregnancy". Drugs.com. Archived from the original on 17 May 2016. Retrieved 9 June 2016. Dexamethasone is only recommended for use during pregnancy when there are no alternatives and benefit outweighs risk.
  2. ^ "Dexamethasone Juno (Juno Pharmaceuticals Pty Ltd)". Department of Health and Aged Care. Archived from the original on 18 March 2023.
  3. ^ "Ozurdex- dexamethasone implant". DailyMed. 30 October 2020. Archived from the original on 27 March 2022. Retrieved 27 March 2022.
  4. ^ "Dexamethasone sodium phosphate solution/ drops". DailyMed. 31 July 2020. Archived from the original on 27 January 2022. Retrieved 27 March 2022.
  5. ^ "Dexycu- dexamethasone injection, suspension". DailyMed. 20 December 2021. Archived from the original on 27 March 2022. Retrieved 27 March 2022.
  6. ^ "Ozurdex EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 27 October 2020. Retrieved 24 October 2020.
  7. ^ "Neofordex EPAR". European Medicines Agency (EMA). 25 July 2014. Archived from the original on 7 October 2024. Retrieved 24 October 2020.
  8. ^ Dogra P, Vijayashankar NP (14 September 2020). "Dexamethasone Suppression Test". StatPearls (14 September 2020). PMID 31194457.
  9. ^ Jobe AH, Milad MA, Peppard T, Jusko WJ (March 2020). "Pharmacokinetics and Pharmacodynamics of Intramuscular and Oral Betamethasone and Dexamethasone in Reproductive Age Women in India". Clinical and Translational Science. 13 (2): 391–99. doi:10.1111/cts.12724. PMC 7070803. PMID 31808984.
  10. ^ a b c d e f g h i "Dexamethasone". The American Society of Health-System Pharmacists. Archived from the original on 31 August 2017. Retrieved 29 July 2015.
  11. ^ Wilkinson IB (13 July 2017). Oxford Handbook of Clinical Medicine. OUP Oxford. p. 176. ISBN 978-0-19-968990-3.
  12. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014. Drugs which have been taken by a large number of pregnant women and women of childbearing age without any proven increase in the frequency of malformations or other direct or indirect harmful effects on the fetus having been observed.
  13. ^ "Drugs@FDA: Dexamethasone". U.S. Food and Drug Administration (FDA). Archived from the original on 30 November 2017. Retrieved 27 March 2022.
  14. ^ Rankovic Z, Hargreaves R, Bingham M (2012). Drug discovery and medicinal chemistry for psychiatric disorders. Cambridge: Royal Society of Chemistry. p. 286. ISBN 9781849733656. Archived from the original on 5 March 2016.
  15. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN 9783527607495. Archived from the original on 10 January 2023. Retrieved 17 June 2020.
  16. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  17. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  18. ^ "Dexamethasone Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  19. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  20. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  21. ^ "Dexamethasone; Neomycin; Polymyxin B Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.

Dexamethasone

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