Fluticasone

Fluticasone
Names
Other namesFluticasone propionate, fluticasone furoate
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-octahydrocyclopenta[a]phenanthrene-17-carbothioate
Clinical data
Drug classGlucocorticoid[1]
Main usesAsthma, COPD, allergic rhinitis[1][2]
Side effectsInhaled: Upper respiratory tract infections, throat irritation, candidiasis, cough, headache[1]
Nose: Burning, nosebleeds, nausea, sore throat[2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		Intranasal, inhaled, topical
External links
AHFS/Drugs.comInhaled: Monograph
Nose: Monograph
Legal
Legal status
Pharmacokinetics
Bioavailability0.51% (Intranasal)
Protein binding91.0%
MetabolismIntranasal
Liver (CYP3A4-mediated)
Elimination half-life10 hours
ExcretionEye
Chemical and physical data
FormulaC22H27F3O4S
Molar mass444.51 g·mol−1
3D model (JSmol)
SMILES
  • O=C(SCF)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)[C@@H](F)C[C@H]4[C@@H]2C[C@H]3C)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 checkY
  • Key:MGNNYOODZCAHBA-GQKYHHCASA-N checkY

Fluticasone is a steroid which is used to treat asthma, COPD, and allergic rhinitis.[1][2] For asthma and COPD it is used for long term management.[1] It is used by breathing it into the lungs or as a nasal spray.[1][2]

Common side effects of the inhaled form include upper respiratory tract infections, throat irritation, candidiasis, cough, and headache.[1] Commons side effects of the nasal spray include a brief period of burning, nosebleeds, nausea, and sore throat.[2] It comes in two main forms fluticasone propionate and fluticasone furoate.[3]

Fluticasone propionate was patented in 1980, and approved for medical use in 1990.[4] It is on the World Health Organization's List of Essential Medicines as an alternative to budesonide.[5] In the United Kingdom 60 doses of 250 micrograms for breathing in costs the NHS about £25.[3] In 2018, it was the sixteenth most commonly prescribed medication in the United States, with more than 34 million prescriptions.[6][7] It is also available in combination as fluticasone/formoterol and fluticasone/salmeterol, among others.[3]

Medical uses

Combinations

Chemistry

There are two manufactured forms.[8][9][10][11][12] They are both esters, fluticasone furoate and fluticasone propionate.[10][9][11][13]

Chemically it is known as 6α,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.

References

  1. 1 2 3 4 5 6 7 "Fluticasone (Systemic, Oral Inhalation) Monograph for Professionals". Drugs.com. Archived from the original on 25 January 2021. Retrieved 14 December 2021.
  2. 1 2 3 4 5 "Fluticasone (EENT) Monograph for Professionals". Drugs.com. Archived from the original on 24 January 2021. Retrieved 14 December 2021.
  3. 1 2 3 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 278. ISBN 978-0857114105.
  4. ↑ Fischer, János; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 487. ISBN 9783527607495. Archived from the original on 2019-02-28. Retrieved 2021-12-14.
  5. ↑ 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.
  6. ↑ "The Top 300 of 2021". ClinCalc. Archived from the original on 12 February 2021. Retrieved 18 February 2021.
  7. ↑ "Fluticasone - Drug Usage Statistics". ClinCalc. Archived from the original on 12 April 2020. Retrieved 18 February 2021.
  8. ↑ 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. Archived from the original on 28 August 2021. Retrieved 20 February 2021.
  9. 1 2 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 1337–. ISBN 978-3-88763-075-1. Archived from the original on 2021-08-28. Retrieved 2021-02-20.
  10. 1 2 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. Archived from the original on 28 August 2021. Retrieved 20 February 2021.
  11. 1 2 "Archive copy". Archived from the original on 2019-04-07. Retrieved 2021-02-20.{{cite web}}: CS1 maint: archived copy as title (link)
  12. ↑ 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. Archived from the original on 2014-01-01. Retrieved 2021-02-20.
  13. ↑ Spratto GR, Woods AL (2012). Delmar Nurse's Drug Handbook 2012. Cengage Learning. p. 748. ISBN 978-1111310653. Archived from the original on 2014-01-01. Retrieved 2021-02-20.
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