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    Chemistry

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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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    01-Jun-2021
    26-Nov-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    (USD/KGS)    		 Number of Transactions

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    DOSAGE - TABLET;ORAL - 250MCG

    USFDA APPLICATION NUMBER - 22522

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