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dexamethasone

File:Dexamethasone_structure.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ422252· pop 50· linked from 1,357 articles

dexamethasone

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Also known as Decadron®, desametasone, fluormethylprednisolone, DXM833

Dexamethasone is a fluorinated glucocorticoid medication 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), and along with antibiotics in tuberculosis. In adrenocortical insufficiency, it may be used in combination with a mineralocorticoid medication such as fludrocortisone. In preterm labor, it may be used to improve outcomes in the baby. It may be given by mouth, as an injection into a mu

OverviewAI-generated

Dexamethasone is a chemical compound with the formula C₂₂H₂₉FO₅. Its molecular mass is listed as 392.19990224799994, while its weight is recorded as 392.5. The substance has a defined daily dose of 1.5.

Physicochemical properties include a water/octanol partition coefficient of 1.83 and an xlogp value of 1.9. The compound features a topological polar surface area of 94.8, with three hydrogen bond donors and six hydrogen bond acceptors. It carries a charge of 0.

Literature references for dexamethasone number 88,713. The subject is referenced by 1,357 other encyclopedia articles.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.Verifiedfields
changed
Drug.Watchedfields
changed
Drug.verifiedrevid
443584169
Drug.image
Dexamethasone structure.svg
Drug.image_class
skin-invert-image
Drug.alt
Skeletal formula of dexamethasone
Drug.image2
Dexamethasone 3D ball.png
Drug.image_class2
bg-transparent
Drug.alt2
Ball-and-stick model of the dexamethasone molecule
Drug.caption
Dexamethasone molecular structure
Drug.tradename
Decadron, Ozurdex, Dexycu, others
Drug.MedlinePlus
a682792
Drug.DailyMedID
Dexamethasone
Drug.pregnancy_AU
A
Drug.routes_of_administration
By mouth, intravenous, intramuscular, subcutaneous, intraosseous, intravitreal, eye drop
Drug.caption2
3D representation of dexamethasone
Drug.ATC_prefix
A01
Drug.ATC_suffix
AC02

via Wikipedia infobox

Chemical data

Formula
C22H29FO5
Molecular weight
392.5 g/mol
IUPAC name
(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
SMILES
C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C
InChIKey
UREBDLICKHMUKA-CXSFZGCWSA-N
XLogP
1.9
Polar surface area
94.8 Ų
H-bond donors
3
H-bond acceptors
6
Formal charge
0

via PubChem

Wikidata facts

Has part
hydrogen
Mass
392.19990224799994
Has use
medication
Show 12 more facts
medical condition treated
COVID-19
found in taxon
Colletotrichum
chemical formula
C₂₂H₂₉FO₅
canonical SMILES
CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C
isomeric SMILES
C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C
Commons category
Dexamethasone
has characteristic
bitterness
World Health Organisation international non-proprietary name
dexamethasone
subject has role
essential medicine
partition coefficient water/octanol
1.83
defined daily dose
1.5
stereoisomer of
betamethasone
Sources (5)

via Wikidata · CC0

~22 min read

Encyclopedic overview

28 sections
Contents
  • Medical uses
  • Anti-inflammatory
  • Cancer
  • COVID-19
  • Surgery
  • Endocrine
  • Pregnancy
  • High-altitude illnesses
  • Nausea and vomiting
  • Sore throat
  • Contraindications
  • Adverse effects
  • Common
  • Unknown frequency
  • Withdrawal
  • Interactions
  • Pharmacology
  • Pharmacodynamics
  • Chemistry
  • Synthesis
  • Spectroscopy
  • History
  • Society and culture
  • Price
  • Nonmedical use
  • Veterinary use
  • References
  • External links

Dexamethasone is a fluorinated glucocorticoid medication 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), and along with antibiotics in tuberculosis. In adrenocortical insufficiency, it may be used in combination with a mineralocorticoid medication such as fludrocortisone. In preterm labor, it may be used to improve outcomes in the baby. 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. The effects of dexamethasone are frequently seen within a day and last for about three days.

The long-term use of dexamethasone may result in thrush, bone loss, cataracts, easy bruising, or muscle weakness. 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. 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. It should not be taken when breastfeeding. Dexamethasone has anti-inflammatory and immunosuppressant effects.

Excerpted from Wikipedia’s “dexamethasone” article, available under the CC BY-SA 4.0 licence.

Gallery (19)