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    Also known as: 936727-05-8, Vx-809, Vx 809, Vx809, Vrt-826809, 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid
    Molecular Formula
    C24H18F2N2O5
    Molecular Weight
    452.4  g/mol
    InChI Key
    UFSKUSARDNFIRC-UHFFFAOYSA-N
    FDA UNII
    EGP8L81APK
    Lumacaftor
    Lumacaftor is a drug used in combination with [DB08820] as the fixed dose combination product Orkambi for the management of Cystic Fibrosis (CF) in patients aged 6 years and older. Cystic Fibrosis is an autosomal recessive disorder caused by one of several different mutations in the gene for the Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) protein, a transmembrane ion channel involved in the transport of chloride and sodium ions across cell membranes of the lungs, pancreas, and other organs. Mutations in the CFTR gene result in altered production, misfolding, or function of the CFTR protein and consequently abnormal fluid and ion transport across cell membranes. As a result, CF patients produce thick, sticky mucus that clogs the ducts of organs where it is produced making patients more susceptible to infections, lung damage, pancreatic insufficiency, and malnutrition. Lumacaftor improves CF symptoms and underlying disease pathology by aiding the conformational stability of F508del-mutated CFTR proteins, preventing misfolding and resulting in increased processing and trafficking of mature protein to the cell surface. Results from clinical trials indicated that treatment with Orkambi (lumacaftor/ivacaftor) results in improved lung function, reduced chance of experiencing a pulmonary exacerbation, increased weight gain, and improvements in CF symptoms. This data has been heavily scrutinized, however, with clinical trials showing only modest improvements despite a hefty yearly cost of $259,000 for Orkambi. Improvements in lung function (ppFEV1) were found to be statistically significant, but minimal, with only a 2.6-3.0% change from baseline with more than 70% of patients failing to achieve an absolute improvement of at least 5%. A wide variety of CFTR mutations correlate to the Cystic Fibrosis phenotype and are associated with differing levels of disease severity. The most common mutation, affecting approximately 70% of patients with CF worldwide, is known as F508del-CFTR, or delta-F508 (F508), in which a deletion in the amino acid phenylalanine at position 508 results in impaired production of the CFTR protein, thereby causing a significant reduction in the amount of ion transporter present on cell membranes. When used in combination with [DB08820] as the fixed dose combination product Orkambi, lumacaftor is specific for the management of CF in patients with delta-F508 mutations as it acts as a protein-folding chaperone, aiding the conformational stability of the mutated CFTR protein. Consequently, lumacaftor increases successful production of CFTR ion channels and the total number of receptors available for use at the cell membrane for fluid and ion transport. The next most common mutation, G551D, affecting 4-5% of CF patients worldwide, is characterized as a missense mutation, whereby there is sufficient amount of protein at the cell surface, but opening and closing mechanisms of the channel are altered. Treatment of patients with G551D and other rarer missense mutations is usually managed with [DB08820] (Kalydeco), as it aids with altered gating mechanisms by potentiating channel opening probability of CFTR protein. Prior to the development of lumacaftor and [DB08820] (Kalydeco), management of CF primarily involved therapies for the control of infections, nutritional support, clearance of mucus, and management of symptoms rather than improvements in the underlying disease process. Approved for use by the Food and Drug Administration in July 2015 and by Health Canada in January 2016, Orkambi was the first combination product approved for the management of Cystic Fibrosis with delta-F508 mutations. Ivacaftor is manufactured and distributed by Vertex Pharmaceuticals.
    The mechanism of action of lumacaftor is as a Cytochrome P450 3A Inducer, and Cytochrome P450 2B6 Inducer, and Cytochrome P450 2C8 Inducer, and Cytochrome P450 2C9 Inducer, and Cytochrome P450 2C19 Inducer, and Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C9 Inhibitor, and P-Glycoprotein Inducer, and P-Glycoprotein Inhibitor.
    1 2D Structure

    Lumacaftor

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[6-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3-methylpyridin-2-yl]benzoic acid
    2.1.2 InChI
    InChI=1S/C24H18F2N2O5/c1-13-5-8-19(27-20(13)14-3-2-4-15(11-14)21(29)30)28-22(31)23(9-10-23)16-6-7-17-18(12-16)33-24(25,26)32-17/h2-8,11-12H,9-10H2,1H3,(H,29,30)(H,27,28,31)
    2.1.3 InChI Key
    UFSKUSARDNFIRC-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(N=C(C=C1)NC(=O)C2(CC2)C3=CC4=C(C=C3)OC(O4)(F)F)C5=CC(=CC=C5)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    EGP8L81APK
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Vx 809

    2. Vx-809

    3. Vx809

    2.3.2 Depositor-Supplied Synonyms

    1. 936727-05-8

    2. Vx-809

    3. Vx 809

    4. Vx809

    5. Vrt-826809

    6. 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic Acid

    7. Vrt 826809

    8. Vx-809 (lumacaftor)

    9. Egp8l81apk

    10. 3-(6-{[1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-benzoicacid

    11. 3-(6-{[1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-benzoic Acid

    12. 3-[6-[[1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropanecarbonyl]amino]-3-methylpyridin-2-yl]benzoic Acid

    13. Lumacaftor (usan)

    14. 3-(6-{[1-(2,2-difluoro-2h-1,3-benzodioxol-5-yl)cyclopropane-1-carbonyl]amino}-3-methylpyridin-2-yl)benzoic Acid

    15. Lumacaftor [usan]

    16. 3-(6-(1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropane-1-carboxamido)-3-methylpyridin-2-yl)benzoic Acid

    17. 3-(6-[[1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino]-3-methyl-pyridin-2-yl)-benzoic Acid

    18. 3-(6-{[1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)-be

    19. 3-(6-{[1-(2,2-difluorobenzo[1,3]dioxol-5-yl)cyclopropanecarbonyl]-amino}-3-methyl-pyridin-2-yl)benzoic Acid

    20. Benzoic Acid, 3-(6-(((1-(2,2-difluoro-1,3-benzodioxol-5-yl)cyclopropyl)carbonyl)amino)-3-methyl-2-pyridinyl)-

    21. Lumacaftor [inn]

    22. Lumacaftor [usan:inn]

    23. Unii-egp8l81apk

    24. Vx8

    25. Lumacaftor [mi]

    26. Lumacaftor (vx-809)

    27. Lumacaftor [who-dd]

    28. Lumacaftor(vx-809vx809)

    29. Mls006011120

    30. Schembl377028

    31. Gtpl7481

    32. Chembl2103870

    33. Lumacaftor [orange Book]

    34. Chebi:90951

    35. Dtxsid30239523

    36. Ex-a178

    37. Hms3655e05

    38. Orkambi Component Lumacaftor

    39. Amy14931

    40. Bcp02305

    41. Bdbm50289703

    42. Mfcd16659051

    43. S1565

    44. Zinc64033452

    45. Akos015920205

    46. Lumacaftor Component Of Orkambi

    47. Ccg-269253

    48. Cs-0479

    49. Db09280

    50. Pb19466

    51. Ncgc00346550-01

    52. Ncgc00346550-02

    53. Ncgc00346550-05

    54. Ac-23172

    55. As-31756

    56. Hy-13262

    57. Smr004702901

    58. Ft-0757817

    59. Sw219911-1

    60. A25628

    61. D10134

    62. J-690399

    63. Q6703005

    64. 3-(6-(1-(2,2-difluorobenzo(d) (1,3)dioxyl-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic Acid

    65. 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) Cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic Acid

    66. 3-(6-{[1-(2,2-difluoro-2h-1,3-benzodioxol-5-yl)cyclopropane-1-carbonyl]amino}-3-methylpyridin-2-yl)benzoic Acid; Vx-809

    67. 3-(6-{[1-(2,2-difluorobenzo[1,3]dioxol-5-yl)cyclopropanecarbonyl]amino}-3-methyl-pyridin-2-yl)benzoic Acid

    2.4 Create Date
    2007-08-20
    3 Chemical and Physical Properties
    Molecular Weight 452.4 g/mol
    Molecular Formula C24H18F2N2O5
    XLogP34.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass452.11837800 g/mol
    Monoisotopic Mass452.11837800 g/mol
    Topological Polar Surface Area97.8 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity776
    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 Indication

    When given in combination with [DB08820] as the fixed dose combination product Orkambi, lumacaftor is indicated for the treatment of cystic fibrosis (CF) in patients age 6 years and older who are homozygous for the F508del mutation in the CFTR gene.

    FDA Label

    Treatment of cystic fibrosis

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Results from clinical trials indicated that treatment with Orkambi (lumacaftor/ [DB08820]) results in improved lung function, reduced chance of experiencing a pulmonary exacerbation, reduced sweat chloride, increased weight gain, and improvements in CF symptoms and quality of life. Orkambi was not found to increase the QTc interval to any clinically relevant extent.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    LUMACAFTOR
    5.2.2 FDA UNII
    EGP8L81APK
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors
    5.3 ATC Code

    R07AX30

    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

    5.4 Absorption, Distribution and Excretion

    Absorption

    Following administration of Orkambi (lumacaftor/[DB08820]) with fat containing foods, peak plasma concentrations were reached at 4 hours (Tmax). It's recommended that Orkambi should be taken with fat-containing foods as they increase absorption of lumacaftor by approximately 2-fold, and[DB08820 by 3-fold.

    Route of Elimination

    Lumacaftor is primarily excreted unchanged in the feces (51%). A minimal amount of the parent compound and its metabolites are excreted in the urine.

    Volume of Distribution

    Following oral administration of 200 mg of lumacaftor every 24 hours to cystic fibrosis patients in a fed state for 28 days, the mean (+/-SD) for apparent volumes of distribution was 86.0 (69.8) L.

    Clearance

    The typical apparent clearance, CL/F (CV), of lumacaftor was estimated to be 2.38 L/hr.

    5.5 Metabolism/Metabolites

    Lumacaftor is mostly excreted unchanged in the feces and is not extensively metabolized. When metabolism does occur, oxidation and glucuronidation are the main processes involved.

    5.6 Biological Half-Life

    The half-life of lumacaftor is approximately 26 hours.

    5.7 Mechanism of Action

    Lumacaftor improves CF symptoms and underlying disease pathology by aiding the conformational stability of F508del-mutated CFTR, resulting in increased processing and trafficking of mature protein to the cell surface. More specifically, lumacaftor acts as a protein-folding chaperone, preventing misfolding of CFTR ion channels and consequent destruction during processing in the endoplasmic reticulum.

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    DMF Number : 33887

    Submission : 2019-06-12

    Status : Active

    Type : II

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