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Roflumilast

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Roflumilast

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Roflumilast
Systematic (IUPAC) name
3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-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. C(US)
Legal status POM (UK) ℞-only (US)
Routes Oral
Identifiers
CAS number 162401-32-3 N
ATC code R03DX07
PubChem CID 158787
ChemSpider 139677 YesY
UNII 0P6C6ZOP5U YesY
ChEMBL CHEMBL193240 N
Chemical data
Formula C17H14Cl2F2N2O3 
Mol. mass 403.207 g/mol
SMILES eMolecules & PubChem
 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 antiinflammatory 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).[1][2][3][4] While roflumilast was found to be effective in clinical trials, it produced several dose-limiting side effects including nausea, diarrhoea and headache, and development is continuing in an attempt to minimise the incidence of side effects while retaining clinical efficacy.[5]

In June 2010, Daxas was approved in the EU for severe COPD associated with chronic bronchitis.[6] In March 2011, Daliresp gained FDA approval in the US for reducing COPD exacerbations.[7]

Chemical synthesis

Chemical synthesis:[8]

Roflumilast syn.png

References

  1. ^ 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. ISSN 1178-2005. PMC 2695611. PMID 18044684. http://www.dovepress.com/getfile.php?fileID=971. 
  2. ^ 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 & Experimental Allergy 38 (5): 847–56. doi:10.1111/j.1365-2222.2008.02950.x. ISSN 1365-2222. PMID 18307529. 
  3. ^ Hohlfeld, JM; Schoenfeld, K; Lavae-Mokhtari, M; Schaumann, F; Mueller, M; Bredenbroeker, D; Krug, N; Hermann, R (August 2008). "Roflumilast attenuates pulmonary inflammation upon segmental endotoxin challenge in healthy subjects: a randomized placebo-controlled trial". Pulmonary Pharmacology & Therapeutics 21 (4): 616–23. doi:10.1016/j.pupt.2008.02.002. ISSN 1094-5539. PMID 18374614. 
  4. ^ 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. ISSN 1354-3784. PMID 18447606. 
  5. ^ Spina, D (October 2008). "PDE4 inhibitors: current status". British Journal of Pharmacology 155 (3): 308–15. doi:10.1038/bjp.2008.307. ISSN 1476-5381. PMC 2567892. PMID 18660825. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2567892. 
  6. ^ "Nycomed's Anti-Inflammatory Gains Approval in EU for COPD"
  7. ^ "FDA approves new drug to treat chronic obstructive pulmonary disease" (Press release). U.S. Food and Drug Administration (FDA). March 1, 2011. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm244989.htm. 
  8. ^ Amschler, H.; 1998, U.S. Patent 5,712,298.
PDE1
MMPX • SCH-51866 • Vinpocetine
PDE2
BAY 60-7550 • EHNA
PDE3
Amrinone • Anagrelide • Bucladesine • Cilostamide • Cilostazol • Enoximone • KMUP-1 • Milrinone • Quazinone • RPL-554 • Siguazodan • Trequinsin • Vesnarinone • Zardaverine
PDE4
Arofylline • Cilomilast • CP-80633 • Denbutylline • Drotaverine • Etazolate • Filaminast • Glaucine • HT-0712 • Ibudilast • ICI-63197 • Irsogladine • Luteolin • Mesembrine • Piclamilast • Roflumilast • Rolipram • Ro20-1724 • RPL-554 • YM-976
PDE5
Acetildenafil • Aildenafil • Avanafil • Dipyridamole • Icariin • Lodenafil • Mirodenafil • MY-5445 • Nitrosoprodenafil • Sildenafil • Sulfoaildenafil • T-0156 • Tadalafil • Udenafil • Vardenafil
PDE6
PDE7
PDE9
BAY 73-6691 • SCH-51866
PDE10
Nonselective
Adrenergics, inhalants
other
Glucocorticoids
Anticholinergics/
muscarinic antagonist
Mast cell stabilizers
Xanthines
Eicosanoid inhibition
Combination products

M: RES

anat(n, x, l, c)/phys/devp

proc, drug(R1/2/3/5/6/7)

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