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Also known as: 162401-32-3, Daxas, 3-(cyclopropylmethoxy)-n-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide, Daliresp, By217, Byk20869
Molecular Formula
C17H14Cl2F2N2O3
Molecular Weight
403.2  g/mol
InChI Key
MNDBXUUTURYVHR-UHFFFAOYSA-N
FDA UNII
0P6C6ZOP5U

Roflumilast
Roflumilast is an orally available, long-acting inhibitor of phosphodiesterase (PDE) type 4 (PDE4), with anti-inflammatory and potential antineoplastic activities. Upon administration, roflumilast and its active metabolite roflumilast N-oxide selectively and competitively bind to and inhibit PDE4, which leads to an increase of both intracellular levels of cyclic-3',5'-adenosine monophosphate (cAMP) and cAMP-mediated signaling. cAMP prevents phosphorylation of spleen tyrosine kinase (SYK) and abrogates activation of the PI3K/AKT/mTOR signaling pathway, which may result in the induction of apoptosis. PDE4, a member of the PDE superfamily that hydrolyses cAMP and 3',5'-cyclic guanosine monophosphate (cGMP) to their inactive 5' monophosphates, is upregulated in a variety of cancers and may contribute to chemoresistance; it also plays a key role in inflammation, especially in inflammatory airway diseases.
Roflumilast is a Phosphodiesterase 4 Inhibitor. The mechanism of action of roflumilast is as a Phosphodiesterase 4 Inhibitor.
1 2D Structure

Roflumilast

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
2.1.2 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)
2.1.3 InChI Key
MNDBXUUTURYVHR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CC1COC2=C(C=CC(=C2)C(=O)NC3=C(C=NC=C3Cl)Cl)OC(F)F
2.2 Other Identifiers
2.2.1 UNII
0P6C6ZOP5U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3-cyclopropylmethoxy-4-difluoromethoxy-n-(3,5-di-chloropyrid-4-yl)benzamide

2. Daliresp

2.3.2 Depositor-Supplied Synonyms

1. 162401-32-3

2. Daxas

3. 3-(cyclopropylmethoxy)-n-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide

4. Daliresp

5. By217

6. Byk20869

7. By-217

8. B9302-107

9. By 217

10. 3-(cyclopropylmethoxy)-n-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide

11. Roflumilast (daxas)

12. Benzamide, 3-(cyclopropylmethoxy)-n-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)-

13. Byk-20869

14. 0p6c6zop5u

15. Chembl193240

16. Chebi:47657

17. 3-cyclopropylmethoxy-n-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide

18. Byk 20869

19. Mfcd00938270

20. B 9302-107

21. Rof

22. Libertek

23. Roflumilast [usan]

24. B-9302-107

25. Roflumilast [usan:inn]

26. Unii-0p6c6zop5u

27. Roflumilastum

28. Roflumilast (jan/usan/inn)

29. Apta-2217

30. 1xmu

31. 1xoq

32. Daliresp (tn)

33. Roflumilast- Bio-x

34. 3g4l

35. Roflumilast [mi]

36. Roflumilast [inn]

37. Roflumilast [jan]

38. 3-cyclopropylmethoxy-4-difluoromethoxy-n-(3,5-di-chloropyrid-4-yl)benzamide

39. Roflumilast [vandf]

40. Roflumilast [mart.]

41. Schembl19158

42. Roflumilast [who-dd]

43. Mls006010074

44. Roflumilast [ema Epar]

45. Gtpl6962

46. Dtxsid8044123

47. Apta 2217

48. Bdbm14774

49. Roflumilast, >=98% (hplc)

50. Amy4219

51. Ex-a059

52. Roflumilast [orange Book]

53. Hms3655p21

54. Hms3748c19

55. Hms3884f09

56. Zinc592419

57. Act02619

58. Bcp03736

59. S2131

60. Arq-151/zoryve (roflumilast Cream)

61. Akos005146309

62. Am84550

63. Ccg-268678

64. Cs-0963

65. Db01656

66. Pb29130

67. Ncgc00346566-01

68. Ncgc00346566-09

69. Ac-23383

70. As-14120

71. Br164364

72. Hy-15455

73. Smr002530074

74. Sy008710

75. Bcp0726000146

76. Ft-0660846

77. R0193

78. Sw220196-1

79. A24672

80. D05744

81. Ab01565852_02

82. 401r323

83. Q693482

84. J-510858

85. Brd-k03194791-001-02-2

86. 3- Cyclo-propylmethoxy-4-difluoromethoxy-n- [3, 5-di-chloropyrid-4-yl]- Benzamid

87. Benzamide, 3-(cyclopropylmethoxy)-n-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)-

88. N-(3,5-dichloropyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 403.2 g/mol
Molecular Formula C17H14Cl2F2N2O3
XLogP34.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count7
Exact Mass402.0349540 g/mol
Monoisotopic Mass402.0349540 g/mol
Topological Polar Surface Area60.4 Ų
Heavy Atom Count26
Formal Charge0
Complexity475
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameDaliresp
PubMed HealthRoflumilast (By mouth)
Drug ClassesRespiratory Agent
Drug LabelThe active ingredient in DALIRESP tablets is roflumilast. Roflumilast and its active metabolite (roflumilast N-oxide) are selective phosphodiesterase 4 (PDE4) inhibitors. The chemical name of roflumilast is N-(3,5-dichloropyridin-4-yl)-3-cyclopropylm...
Active IngredientRoflumilast
Dosage FormTablet
RouteOral
Strength500mcg
Market StatusPrescription
CompanyForest Res Inst

2 of 2  
Drug NameDaliresp
PubMed HealthRoflumilast (By mouth)
Drug ClassesRespiratory Agent
Drug LabelThe active ingredient in DALIRESP tablets is roflumilast. Roflumilast and its active metabolite (roflumilast N-oxide) are selective phosphodiesterase 4 (PDE4) inhibitors. The chemical name of roflumilast is N-(3,5-dichloropyridin-4-yl)-3-cyclopropylm...
Active IngredientRoflumilast
Dosage FormTablet
RouteOral
Strength500mcg
Market StatusPrescription
CompanyForest Res Inst

4.2 Drug Indication

Roflumilast is indicated as a treatment to reduce the risk of COPD exacerbations in patients with severe COPD associated with chronic bronchitis and a history of exacerbations. Roflumilast is not a bronchodilator and is not indicated for the relief of acute bronchospasm.


FDA Label


Daxas is indicated for maintenance treatment of severe chronic obstructive pulmonary disease (COPD) (FEV1 post-bronchodilator less than 50% predicted) associated with chronic bronchitis in adult patients with a history of frequent exacerbations as add-on to bronchodilator treatment.


Libertek is indicated for maintenance treatment of severe chronic obstructive pulmonary disease (COPD) (FEV1 post-bronchodilator less than 50% predicted) associated with chronic bronchitis in adult patients with a history of frequent exacerbations as add-on to bronchodilator treatment.


Daliresp is indicated for maintenance treatment of severe chronic obstructive pulmonary disease (COPD) (FEV1 post-bronchodilator less than 50% predicted) associated with chronic bronchitis in adult patients with a history of frequent exacerbations as add-on to bronchodilator treatment.


Chronic obstructive pulmonary disease


5 Pharmacology and Biochemistry
5.1 Pharmacology

Roflumilast (and its active metabolite, roflumilast N-oxide) increases cyclic adenosine-3, 5-monophosphate (cAMP) in lung cells by inhibiting PDE4. Increased cAMP activates PKA, which inactivates transcription factors involved in inflammation. Romflumilast also decreases the amount of sputum neutrophils and eosinophils in COPD patients.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
ROFLUMILAST
5.2.2 FDA UNII
0P6C6ZOP5U
5.2.3 Pharmacological Classes
Phosphodiesterase 4 Inhibitors [MoA]; Phosphodiesterase 4 Inhibitor [EPC]
5.3 ATC Code

R03DX07


R03DX08


R03DX07


R03DX07

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03D - Other systemic drugs for obstructive airway diseases

R03DX - Other systemic drugs for obstructive airway diseases

R03DX07 - Roflumilast


5.4 Absorption, Distribution and Excretion

Absorption

After a 500mcg dose, the bioavailability of roflumilast is about 80%. In the fasted state, maximum plasma concentrations are reached in 0.5 to 2 hours. While in the fed state, Cmax is reduced by 40%, Tmax is increased by one hour, and total absorption is unchanged.


Route of Elimination

Roflumilast is excreted 70% in the urine as roflumilast N-oxide.


Volume of Distribution

Roflumilast has a Vd of 2.9L/kg with a dose of 500mcg. Permeability of roflumilast across the blood-brain barrier appears to be poor in rat studies.


Clearance

~9.6 L/hour.


5.5 Metabolism/Metabolites

Roflumilast is metabolized to roflumilast N-oxide, the active metabolite of roflumilast in humans, by CYP3A4 and CYP1A2.


5.6 Biological Half-Life

Plasma half-life of roflumilast is 17 hours and its metabolite is 30 hours (oral dose).


5.7 Mechanism of Action

Roflumilast is a phosphodiesterase-4 (PDE-4) inhibitor which, due to its selective inhibition of the PDE4 isoenzyme, has potential antiinflammatory and antimodulatory effects in the pulmonary system. It is thought that the increased levels of intracellular cyclic AMP are responsible for the therapeutic actions of Roflumilast.


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08-Jan-2021
24-Jun-2024
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Chewable & Orodispersible Aids

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Taste Masking

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Parenteral

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Coating Systems & Additives

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Emulsifying Agents

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Film Formers & Plasticizers

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