Roflumilast

Title: Roflumilast
CAS Registry Number: 162401-32-3
CAS Name: 3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide
Manufacturers' Codes: BY-217
Trademarks: Daxas (Altana)
Molecular Formula: C17H14Cl2F2N2O3
Molecular Weight: 403.21
Percent Composition: C 50.64%, H 3.50%, Cl 17.59%, F 9.42%, N 6.95%, O 11.90%
Literature References: Selective phosphodiesterase 4 (PDE4) inhibitor. Prepn: D. Flockerzi et al., WO 9501338; H. Amschler, US 5712298 (1995, 1998 both to Byk-Gulden). Pharmacology: A. Hatzelmann, C. Schudt, J. Pharmacol. Exp. Ther. 297, 267 (2001); D. S. Bundschuh et al., ibid. 280. Clinical evaluation in allergic rhinitis: B. M. W. Schmidt et al., J. Allergy Clin. Immunol. 108, 530 (2001); in exercise-induced asthma: W. Timmer et al., J. Clin. Pharmacol. 42, 297 (2002); in COPD: K. F. Rabe et al., Lancet 366, 563 (2005). Comparative review with cilomilast: M. A. Giembycz, Monaldi Arch. Chest Dis. 57, 48-64 (2002).
Properties: Crystals from isopropanol, mp 158°.
Melting point: mp 158°
Therap-Cat: Antiasthmatic; in treatment of chronic obstructive pulmonary disease.
Keywords: Antiasthmatic (Nonbronchodilator); Phosphodiesterase Inhibitor.
Rokitamycin Rolicyprine Rolitetracycline Romurtide Ronidazole

Roflumilast
Roflumilast2DACS.svg
Roflumilast3Dan.gif
Systematic (IUPAC) name
N-(3,5-dichloropyridin-4-yl)-3-cyclopropylmethoxy-4-difluoromethoxy-benzamide
Clinical data
Trade names Daxas, Daliresp
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a611034
Licence data EMA:Link, US FDA:link
Pregnancy cat. B3 (AU) C (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 79%[1][2][3][4]
Protein binding 99%[1][2][3][4]
Metabolism Hepatic via CYP1A2 & CYP3A4[1][2][3][4]
Half-life 17 hours (30 hours [active metabolite])[1][2][3][4]
Excretion Urine (70%)[1][2][3][4]
Identifiers
CAS number 162401-32-3 N
ATC code R03DX07
PubChem CID 158787
ChemSpider 139677 YesY
UNII 0P6C6ZOP5U YesY
ChEBI CHEBI:47657 N
ChEMBL CHEMBL193240 N
Chemical data
Formula C17H14Cl2F2N2O3 
Mol. mass 403.207 g/mol
 N (what is this?)  (verify)

Roflumilast (trade names Daxas, Daliresp) is a drug which acts as a selective, long-acting inhibitor of the enzyme PDE-4. It has anti-inflammatory effects and is under development as an orally administered drug for the treatment of inflammatory conditions of the lungs such as asthma, and chronic obstructive pulmonary disease (COPD).[5][6][7][8]

In June 2010, Daxas was approved in the EU for severe COPD associated with chronic bronchitis.[9] In March 2011, Daliresp gained FDA approval in the US for reducing COPD exacerbations.[10]