Fluticasone

From WikiProjectMed
Jump to navigation Jump to search
Fluticasone
Fluticasone.svg
Names
Other namesFluticasone propionate, fluticasone furoate
  • 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]
Routes of
use
Intranasal, inhaled, topical
External links
AHFS/Drugs.comInhaled: Monograph
Nose: Monograph
US NLMFluticasone
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)
  • 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=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] 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.[5][6] It is also available in combination as fluticasone/formoterol and fluticasone/salmeterol, among others.[3]

Medical uses

Combinations

Chemistry

There are two manufactured forms.[7][8][9][10][11] They are both esters, fluticasone furoate and fluticasone propionate.[9][8][10][12]

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. 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Fluticasone (Systemic, Oral Inhalation) Monograph for Professionals". Drugs.com. Archived from the original on 25 January 2021. Retrieved 14 December 2021.
  2. 2.0 2.1 2.2 2.3 2.4 "Fluticasone (EENT) Monograph for Professionals". Drugs.com. Archived from the original on 24 January 2021. Retrieved 14 December 2021.
  3. 3.0 3.1 3.2 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. "The Top 300 of 2021". ClinCalc. Archived from the original on 12 February 2021. Retrieved 18 February 2021.
  6. "Fluticasone - Drug Usage Statistics". ClinCalc. Archived from the original on 12 April 2020. Retrieved 18 February 2021.
  7. 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.
  8. 8.0 8.1 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.
  9. 9.0 9.1 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.
  10. 10.0 10.1 "Archive copy". Archived from the original on 2019-04-07. Retrieved 2021-02-20.{{cite web}}: CS1 maint: archived copy as title (link)
  11. 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.
  12. 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.

External links

External sites:
Identifiers: