Roflumilast

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
ATC code	R03DX07
PubChem	CID 158787
ChemSpider	139677
UNII	0P6C6ZOP5U
ChEMBL	CHEMBL193240
Chemical data
Formula	C17H14Cl2F2N2O3
Mol. mass	403.207 g/mol
SMILES	eMolecules & PubChem
	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 ;
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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).¹²³⁴ 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

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ "Nycomed's Anti-Inflammatory Gains Approval in EU for COPD"
^ "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.
^ Amschler, H.; 1998, U.S. Patent 5,712,298.

External links

Official website
Daxas European Public Assessment Report (EPAR)

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[pmid18044684-0] 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.

[pmid18307529-1] 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.

[pmid18374614-2] 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.

[pmid18447606-3] 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.

[pmid18660825-4] 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.

[5] "Nycomed's Anti-Inflammatory Gains Approval in EU for COPD"

[6] "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.

[7] Amschler, H.; 1998, U.S. Patent 5,712,298.

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Roflumilast

Contents

Chemical synthesis

See also

References

External links

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