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Revision as of 10:52, 26 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: '').← Previous edit Revision as of 11:02, 26 October 2011 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - added verified revid - updated 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or bugs)Next edit →
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| IUPAC_name = 3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide | IUPAC_name = 3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
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| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
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| ChemSpiderID = 139677 | ChemSpiderID = 139677
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0P6C6ZOP5U | UNII = 0P6C6ZOP5U
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}

Revision as of 11:02, 26 October 2011

Pharmaceutical compound
Roflumilast
Clinical data
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa611034
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Identifiers
IUPAC name
  • 3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.210.960 Edit this at Wikidata
Chemical and physical data
FormulaC17H14Cl2F2N2O3
Molar mass403.207 g/mol g·mol
3D model (JSmol)
SMILES
  • Clc3c(N(OCC1CC1)C(=O)c2ccc(OC(F)F)cc2)c(Cl)cnc3
InChI
  • InChI=1S/C17H14Cl2F2N2O3/c18-13-7-22-8-14(19)15(13)23(25-9-10-1-2-10)16(24)11-3-5-12(6-4-11)26-17(20)21/h3-8,10,17H,1-2,9H2
  • Key:IWONQDOIPBAXGV-UHFFFAOYSA-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). 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.

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

Chemical synthesis

Chemical synthesis:

See also

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.
  2. Herbert, C; Hettiaratchi, A; Webb, DC; Thomas, PS; Foster, PS; Kumar, RK (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. {{cite journal}}: Unknown parameter |month= ignored (help)
  3. Hohlfeld, JM; Schoenfeld, K; Lavae-Mokhtari, M; Schaumann, F; Mueller, M; Bredenbroeker, D; Krug, N; Hermann, R (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. {{cite journal}}: Unknown parameter |month= ignored (help)
  4. Field, SK (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. {{cite journal}}: Unknown parameter |month= ignored (help)
  5. Spina, D (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. {{cite journal}}: Unknown parameter |month= ignored (help)
  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.
  8. Amschler, H.; 1998, U.S. patent 5,712,298.
Phosphodiesterase inhibitors
PDE1
PDE2
PDE3
PDE4
PDE5
PDE7
PDE9
PDE10
PDE11BC11-38
Non-selective
Unsorted
See also: Receptor/signaling modulators
Drugs for obstructive airway diseases: asthma/COPD (R03)
Adrenergics, inhalants
Short-acting β2 agonists
Long-acting β2 agonists
Ultra-long-acting β2 agonists
Other
Glucocorticoids
Anticholinergics/
muscarinic antagonist
Mast cell stabilizers
Xanthines
Eicosanoid inhibition
Leukotriene antagonists
Arachidonate 5-lipoxygenase inhibitors
Thromboxane receptor antagonists
Non-xanthine PDE4 inhibitors
Others/unknown
Combination products


External links

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