Roflumilast

Last updated

Roflumilast
Roflumilast structure.svg
Roflumilast ball-and-stick model.png
Clinical data
Trade names Daxas, Daliresp, Zoryve, others
AHFS/Drugs.com Monograph
MedlinePlus a611034
License data
Pregnancy
category
  • AU:B3
Routes of
administration
By mouth, topical
Drug class PDE4 inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 79% [4] [3] [8] [9]
Protein binding 99% [4] [3] [8] [9]
Metabolism Hepatic via CYP1A2 & CYP3A4 [4] [3] [8] [9]
Elimination half-life 17 hours (30 hours [active metabolite]) [4] [3] [8] [9]
Excretion Urine (70%) [4] [3] [8] [9]
Identifiers
  • 3-(Cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard 100.210.960 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H14Cl2F2N2O3
Molar mass 403.21 g·mol−1
3D model (JSmol)
  • C1CC1COC2=C(C=CC(=C2)C(=O)NC3=C(C=NC=C3Cl)Cl)OC(F)F
  • InChI=1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24) X mark.svgN
  • Key:MNDBXUUTURYVHR-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Roflumilast, sold under the brand name Daxas among others, is a medication used for the treatment of chronic obstructive pulmonary disease, [4] plaque psoriasis, [5] seborrheic dermatitis, [6] and atopic dermatitis. [5] It acts as a selective, long-acting inhibitor of the enzyme phosphodiesterase-4 (PDE-4). [10] It has anti-inflammatory effects. [10] [11] [12]

Contents

It was approved for medical use in the European Union in 2010, [7] in the United States in 2011, [4] and in Canada in 2017. [1] It is available as a generic medication. [13]

Medical uses

Roflumilast is indicated for the treatment of severe chronic obstructive pulmonary disease (COPD), [4] plaque psoriasis, [5] [14] seborrheic dermatitis, [6] and atopic dermatitis, [5] [15]

It is used in the prevention of exacerbations (lung attacks) in severe chronic obstructive pulmonary disease (COPD). [3] [4] [7] [8] [9]

Adverse effects

Common (1–10% incidence) adverse effects include diarrhea, weight loss, nausea, headache, insomnia, decreased appetite, abdominal pain, rhinitis, sinusitis, urinary tract infection, and depression. [4] [3] [8] [9] [16]

Society and culture

In June 2010, it was approved in the European Union for severe COPD associated with chronic bronchitis. [7] [17] In February 2011, it gained FDA approval in the United States for reducing COPD exacerbations. [18] [19]

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References

  1. 1 2 "Daxas Product information". Health Canada . 20 July 2017. Retrieved 13 July 2024.
  2. "Zoryve Product information". Health Canada . 7 November 2023. Retrieved 13 July 2024.
  3. 1 2 3 4 5 6 7 8 "Daxas 250 micrograms tablets - Summary of Product Characteristics (SmPC)". (emc). 11 June 2020. Archived from the original on 19 September 2020. Retrieved 28 September 2020.
  4. 1 2 3 4 5 6 7 8 9 10 11 "Daliresp- roflumilast tablet". DailyMed. 12 March 2020. Archived from the original on 25 March 2021. Retrieved 28 September 2020.
  5. 1 2 3 4 5 "Zoryve- roflumilast cream". DailyMed. 16 August 2022. Archived from the original on 21 January 2023. Retrieved 21 January 2023.
  6. 1 2 3 "Zoryve- roflumilast aerosol, foam". DailyMed. 20 December 2023. Retrieved 13 July 2024.
  7. 1 2 3 4 "Daxas EPAR". European Medicines Agency . 17 September 2018. Archived from the original on 12 August 2020. Retrieved 28 September 2020.
  8. 1 2 3 4 5 6 7 "Daliresp : EPAR - Product Information" (PDF). European Medicines Agency. Takeda GmbH. 26 September 2013. Archived (PDF) from the original on 26 June 2016. Retrieved 18 November 2013.
  9. 1 2 3 4 5 6 7 "roflumilast (Rx) - Daliresp". Medscape Reference. WebMD. Archived from the original on 12 September 2017. Retrieved 18 November 2013.
  10. 1 2 Boswell-Smith V, Spina D (2007). "PDE4 inhibitors as potential therapeutic agents in the treatment of COPD-focus on roflumilast". International Journal of Chronic Obstructive Pulmonary Disease. 2 (2): 121–9. PMC   2695611 . PMID   18044684.
  11. Herbert C, Hettiaratchi A, Webb DC, Thomas PS, Foster PS, Kumar RK (May 2008). "Suppression of cytokine expression by roflumilast and dexamethasone in a model of chronic asthma". Clinical and Experimental Allergy. 38 (5): 847–56. doi:10.1111/j.1365-2222.2008.02950.x. PMID   18307529. S2CID   19050454.
  12. Field SK (May 2008). "Roflumilast: an oral, once-daily selective PDE-4 inhibitor for the management of COPD and asthma". Expert Opinion on Investigational Drugs. 17 (5): 811–8. doi:10.1517/13543784.17.5.811. PMID   18447606. S2CID   73241684.
  13. "2022 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
  14. "FDA Approves Arcutis' Zoryve (Roflumilast) Cream 0.3% For the Treatment of Plaque Psoriasis in Individuals Age 12 and Older" (Press release). Arcutis Biotherapeutics. 29 July 2022. Archived from the original on 1 August 2022. Retrieved 1 August 2022 via GlobeNewswire.
  15. "FDA Approves Atopic Dermatitis Label Expansion for Arcutis' Zoryve Cream". BioSpace. Retrieved 13 July 2024.
  16. Spina D (October 2008). "PDE4 inhibitors: current status". British Journal of Pharmacology. 155 (3): 308–15. doi:10.1038/bjp.2008.307. PMC   2567892 . PMID   18660825.
  17. ""Nycomed's Anti-Inflammatory Gains Approval in EU for COPD"". Archived from the original on 24 August 2017. Retrieved 10 July 2010.
  18. "Drug Approval Package: Daliresp Tablets (roflumilast) NDA #022522". U.S. Food and Drug Administration (FDA). 24 December 1999. Archived from the original on 27 October 2020. Retrieved 28 September 2020.
  19. "FDA approves new drug to treat chronic obstructive pulmonary disease" (Press release). U.S. Food and Drug Administration (FDA). 1 March 2011. Archived from the original on 18 January 2017. Retrieved 16 December 2019.

Further reading