Roflumilast

Roflumilast
drugb
Names
Trade namesDaxas, Daliresp, others
IUPAC name
  • 3-(Cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
Clinical data
Drug classPhosphodiesterase-4 inhibitor (PDE-4)[1]
Main usesChronic obstructive pulmonary disease (COPD)[1]
Side effectsDiarrhea, nausea, headache, back pain, trouble sleeping, dizziness[2]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: B3
  • US: N (Not classified yet)
    Routes of
    use    		By mouth
    Typical dose0.5 mg OD[1]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa611034
    Legal
    License data
    Legal status
    Pharmacokinetics
    Bioavailability79%[4][3][6][7]
    Protein binding99%[4][3][6][7]
    MetabolismLiver via CYP1A2 & CYP3A4[4][3][6][7]
    Elimination half-life17 hours (30 hours [active metabolite])[4][3][6][7]
    ExcretionUrine (70%)[4][3][6][7]
    Chemical and physical data
    FormulaC17H14Cl2F2N2O3
    Molar mass403.21 g·mol−1
    3D model (JSmol)
    SMILES
    • C1CC1COC2=C(C=CC(=C2)C(=O)NC3=C(C=NC=C3Cl)Cl)OC(F)F
    InChI
    • 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

    Roflumilast, sold under the trade name Daxas among others, is a medication used for the long term management of chronic obstructive pulmonary disease (COPD).[1] It is used in those with severe disease.[1] It is taken by mouth.[1]

    Common side effects include diarrhea, nausea, headache, back pain, trouble sleeping, and dizziness.[2] Other side effects can include suicide.[2] It is a selective inhibitor of the enzyme phosphodiesterase-4 (PDE-4) and works by decreasing lung inflammation.[1][5]

    Roflumilast was approved for medical use in Europe in 2010 and the United States in 2011.[5][8][2] In the United Kingdom it costs the NHS about £38 per month as of 2021.[9] This amount in the United States costs about 430 USD.[10]

    Medical uses

    Its primary use is in the prevention of exacerbations in severe chronic obstructive pulmonary disease (COPD).[4][3][6][7][5] It is however unclear if benefits are greater than harms.[11]

    Dosage

    It is taken at a dose of 0.5 mg per day.[1] Some people may be started at half the that dose for the first month.[2]

    Side effects

    Common (1–10% incidence) adverse effects include:[4][3][6][7][12]

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

    References

    1. 1 2 3 4 5 6 7 8 "Roflumilast Monograph for Professionals". Drugs.com. Archived from the original on 25 February 2021. Retrieved 18 October 2021.
    2. 1 2 3 4 5 "DailyMed - DALIRESP- roflumilast tablet". dailymed.nlm.nih.gov. Archived from the original on 25 March 2021. Retrieved 18 October 2021.
    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 "Daliresp- roflumilast tablet". DailyMed. 12 March 2020. Archived from the original on 25 March 2021. Retrieved 28 September 2020.
    5. 1 2 3 4 "Daxas EPAR". European Medicines Agency. Archived from the original on 12 August 2020. Retrieved 28 September 2020.
    6. 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.
    7. 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.
    8. ↑ ""Nycomed's Anti-Inflammatory Gains Approval in EU for COPD"". Archived from the original on 2017-08-24. Retrieved 2021-07-21.
    9. ↑ BNF (80 ed.). BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 286. ISBN 978-0-85711-369-6.{{cite book}}: CS1 maint: date format (link)
    10. ↑ "Daliresp Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 11 April 2021. Retrieved 18 October 2021.
    11. ↑ Ton, Joey (31 October 2011). "#55 Roflumilast – COPD relief at last?". CFPCLearn. Archived from the original on 28 March 2023. Retrieved 18 June 2023.
    12. ↑ 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.
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