Roflumilast

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Roflumilast
Roflumilast structure.svg
Roflumilast ball-and-stick model.png
drugb
Clinical data
Trade namesDaxas, Daliresp, others
AHFS/Drugs.comMonograph
MedlinePlusa611034
License data
Pregnancy
category
  • AU: B3
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability79%[2][1][4][5]
Protein binding99%[2][1][4][5]
MetabolismHepatic via CYP1A2 & CYP3A4[2][1][4][5]
Elimination half-life17 hours (30 hours [active metabolite])[2][1][4][5]
ExcretionUrine (70%)[2][1][4][5]
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 trade name Daxas among others, is a drug that acts as a selective, long-acting inhibitor of the enzyme phosphodiesterase-4 (PDE-4). It has anti-inflammatory effects and is used as an orally administered drug for the treatment of inflammatory conditions of the lungs such as chronic obstructive pulmonary disease (COPD).[6][7][8][9]

In June 2010, it was approved in the European Union for severe COPD associated with chronic bronchitis.[3][10] In February 2011, it gained FDA approval in the United States for reducing COPD exacerbations.[11][12]

Medical uses[edit]

Its primary clinical use is in the prevention of exacerbations (lung attacks) in severe chronic obstructive pulmonary disease (COPD).[2][1]>[4][5][3]

Adverse effects[edit]

Common (1–10% incidence) adverse effects include:[2][1][4][5][13]

  • Diarrhea
  • Weight loss
  • Nausea
  • Headache
  • Insomnia
  • Decreased appetite
  • Abdominal pain
  • Rhinitis
  • Sinusitis
  • Urinary tract infection
  • Depression

References[edit]

  1. ^ a b c d e f g h "Daxas 250 micrograms tablets - Summary of Product Characteristics (SmPC)". (emc). 11 June 2020. Retrieved 28 September 2020.
  2. ^ a b c d e f g h "Daliresp- roflumilast tablet". DailyMed. 12 March 2020. Retrieved 28 September 2020.
  3. ^ a b c "Daxas EPAR". European Medicines Agency. Retrieved 28 September 2020.
  4. ^ a b c d e f g "Daliresp : EPAR - Product Information" (PDF). European Medicines Agency. Takeda GmbH. 26 September 2013. Retrieved 18 November 2013.
  5. ^ a b c d e f g "roflumilast (Rx) - Daliresp". Medscape Reference. WebMD. Retrieved 18 November 2013.
  6. ^ 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.
  7. ^ 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.
  8. ^ Hohlfeld JM, Schoenfeld K, Lavae-Mokhtari M, Schaumann F, Mueller M, Bredenbroeker D, et al. (August 2008). "Roflumilast attenuates pulmonary inflammation upon segmental endotoxin challenge in healthy subjects: a randomized placebo-controlled trial" (PDF). Pulmonary Pharmacology & Therapeutics. 21 (4): 616–23. doi:10.1016/j.pupt.2008.02.002. PMID 18374614.
  9. ^ 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.
  10. ^ "Nycomed's Anti-Inflammatory Gains Approval in EU for COPD"
  11. ^ "Drug Approval Package: Daliresp Tablets (roflumilast) NDA #022522". U.S. Food and Drug Administration (FDA). 24 December 1999. Retrieved 28 September 2020. Lay summary (PDF).
  12. ^ "FDA approves new drug to treat chronic obstructive pulmonary disease" (Press release). U.S. Food and Drug Administration (FDA). March 1, 2011.[dead link]
  13. ^ 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.

External links[edit]

  • "Roflumilast". Drug Information Portal. U.S. National Library of Medicine.