Roflumilast

Roflumilast
Clinical data
Trade names	Daxas, Daliresp, Zoryve, others
AHFS/Drugs.com	Monograph
MedlinePlus	a611034
License data	US DailyMed: Roflumilast;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth, topical
Drug class	PDE4 inhibitor
ATC code	R03DX07 (WHO) D05AX06 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	79%
Protein binding	99%
Metabolism	Hepatic via CYP1A2 & CYP3A4
Elimination half-life	17 hours (30 hours [active metabolite])
Excretion	Urine (70%)
Identifiers
	IUPAC name 3-(Cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide;
CAS Number	162401-32-3 ;
PubChem CID	449193;
IUPHAR/BPS	6962;
DrugBank	DB01656 ;
ChemSpider	395793 ;
UNII	0P6C6ZOP5U;
KEGG	D05744;
ChEBI	CHEBI:47657 ;
ChEMBL	ChEMBL193240 ;
PDB ligand	ROF (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8044123 ;
ECHA InfoCard	100.210.960
Chemical and physical data
Formula	C17H14Cl2F2N2O3
Molar mass	403.21 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:MNDBXUUTURYVHR-UHFFFAOYSA-N ;
	(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]

^ ^a ^b "Daxas Product information". Health Canada. 20 July 2017. Retrieved 13 July 2024.
^ "Zoryve Product information". Health Canada. 7 November 2023. Retrieved 13 July 2024.
^ ^a ^b ^c ^d ^e ^f Cite error: The named reference Daxas SmPC was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g ^h "Daliresp- roflumilast tablet". DailyMed. 12 March 2020. Archived from the original on 25 March 2021. Retrieved 28 September 2020.
^ ^a ^b ^c Cite error: The named reference Zoryve cream FDA label was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference Zoryve foam FDA label was invoked but never defined (see the help page).
^ ^a ^b "Daxas EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 12 August 2020. Retrieved 28 September 2020.
^ ^a ^b ^c ^d ^e Cite error: The named reference EMA was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e Cite error: The named reference MSR was invoked but never defined (see the help page).
^ ^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.
^ 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.
^ 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.
^ "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.

[Daxas_CA_PI-1] "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.

[Daxas_SmPC-3] ^ ^a ^b ^c ^d ^e ^f Cite error: The named reference Daxas SmPC was invoked but never defined (see the help page).

[Daliresp_FDA_label-4] ^ ^a ^b ^c ^d ^e ^f ^g ^h "Daliresp- roflumilast tablet". DailyMed. 12 March 2020. Archived from the original on 25 March 2021. Retrieved 28 September 2020.

[Zoryve_cream_FDA_label-5] Cite error: The named reference Zoryve cream FDA label was invoked but never defined (see the help page).

[Zoryve_foam_FDA_label-6] Cite error: The named reference Zoryve foam FDA label was invoked but never defined (see the help page).

[Daxas_EPAR-7] "Daxas EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 12 August 2020. Retrieved 28 September 2020.

[EMA-8] Cite error: The named reference EMA was invoked but never defined (see the help page).

[MSR-9] Cite error: The named reference MSR was invoked but never defined (see the help page).

[pmid18044684-10] 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.

[pmid18307529-11] 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.

[pmid18447606-12] 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.

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