Roflumilast

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]

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[1][2] UK: POM (Prescription only)[3] US: ℞-only[4][5][6] EU: Rx-only[7]
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
IUPAC name 3-(Cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
CAS Number	162401-32-3 N
PubChem CID	449193
IUPHAR/BPS	6962
DrugBank	DB01656 Y
ChemSpider	395793 N
UNII	0P6C6ZOP5U
KEGG	D05744
ChEBI	CHEBI:47657 N
ChEMBL	ChEMBL193240 N
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) N Key:MNDBXUUTURYVHR-UHFFFAOYSA-N N
NY (what is this?)  (verify)

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

Legal status

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]