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Fluticasone

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Chemical compound

Pharmaceutical compound
Fluticasone
Clinical data
Other names6α,9α-Difluoro-11β,17α-dihydroxy-16α-methyl-21-thia-21-fluoromethylpregna-1,4-dien-3,20-dione; S-(Fluoromethyl)-6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate
Routes of
administration
Intranasal, inhalation, topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability0.51% (Intranasal)
Protein binding91.0%
MetabolismIntranasal
Liver (CYP3A4-mediated)
Elimination half-life10 hours
ExcretionKidney
Identifiers
IUPAC name
  • S-fluoromethyl (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopentaphenanthrene-17-carbothioate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H27F3O4S
Molar mass444.51 g·mol
3D model (JSmol)
SMILES
  • O=C(SCF)3(O)2(C(O)4(F)/1(\C(=C/C(=O)\C=C\1)(F)C42C3C)C)C
InChI
  • InChI=1S/C22H27F3O4S/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-19(15,2)21(14,25)17(27)9-20(13,3)22(11,29)18(28)30-10-23/h4-5,7,11,13-14,16-17,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
  • Key:MGNNYOODZCAHBA-GQKYHHCASA-N
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Fluticasone is a manufactured glucocorticoid used to treat nasal congestion. Both the esters, fluticasone propionate (sold as Flovent) and fluticasone furoate, are also used as topical anti-inflammatories and inhaled corticosteroids, and are used much more commonly in comparison.

It is on the World Health Organization's List of Essential Medicines. In 2022, it was the 25th most commonly prescribed medication in the United States, with more than 22 million prescriptions, although it is also sold over-the-counter (OTC).

See also

References

  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 574–. ISBN 978-1-4757-2085-3.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 1337–. ISBN 978-3-88763-075-1.
  3. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 124–. ISBN 978-94-011-4439-1.
  4. ^ "Fluticasone - FDA prescribing information, side effects and uses".
  5. Briggs GG, Freeman RK, Yaffe SJ (2012). Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk. Lippincott Williams & Wilkins. p. 600. ISBN 978-1451153590.
  6. Spratto GR, Woods AL (2012). Delmar Nurse's Drug Handbook 2012. Cengage Learning. p. 748. ISBN 978-1111310653.
  7. World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  8. "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  9. "Fluticasone Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  10. "Fluticasone Nasal Spray". Retrieved 21 October 2022.
Glucocorticoids and antiglucocorticoids (D07, H02)
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