Roflumilast

Roflumilast
Clinical data
Trade namesDaxas, Daliresp, Zoryve, others
AHFS/Drugs.comMonograph
MedlinePlusa611034
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, topical
Drug classPDE4 inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability79%[4][3][8][9]
Protein binding99%[4][3][8][9]
MetabolismHepatic via CYP1A2 & CYP3A4[4][3][8][9]
Elimination half-life17 hours (30 hours [active metabolite])[4][3][8][9]
ExcretionUrine (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 InfoCard100.210.960 Edit this at Wikidata
Chemical and physical data
FormulaC17H14Cl2F2N2O3
Molar mass403.21 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) ☒N
  • Key:MNDBXUUTURYVHR-UHFFFAOYSA-N ☒N
 ☒NcheckY (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]

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]

References

  1. ^ a b "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. ^ a b c d e f g h "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. ^ a b c d e f g h i j k "Daliresp- roflumilast tablet". DailyMed. 12 March 2020. Archived from the original on 25 March 2021. Retrieved 28 September 2020.
  5. ^ a b c d e "Zoryve- roflumilast cream". DailyMed. 16 August 2022. Archived from the original on 21 January 2023. Retrieved 21 January 2023.
  6. ^ a b c "Zoryve- roflumilast aerosol, foam". DailyMed. 20 December 2023. Retrieved 13 July 2024.
  7. ^ a b c d "Daxas EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 12 August 2020. Retrieved 28 September 2020.
  8. ^ a b c d e f g "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. ^ a b c d e f g "roflumilast (Rx) - Daliresp". Medscape Reference. WebMD. Archived from the original on 12 September 2017. Retrieved 18 November 2013.
  10. ^ a b 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