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    Chemistry

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    Also known as: Eliglustat hemitartrate, Cerdelga, 928659-70-5, Agalsidase beta, Eliglustat (hemitartrate), Genz-112638
    Molecular Formula
    C50H78N4O14
    Molecular Weight
    959.2  g/mol
    InChI Key
    KUBARPMUNHKBIQ-VTHUDJRQSA-N
    FDA UNII
    N0493335P3
    Eliglustat
    Agalsidase beta is a recombinant human -galactosidase A similar to [agalsidase alfa]. While patients generally do not experience a clinically significant difference in outcomes between the two drugs, some patients may experience greater benefit with agalsidase beta. Use of agalsidase beta has decreased in Europe, in favor of agalsidase alfa, after a contamination event in 2009. Agalsidase beta was granted FDA approval on 24 April 2003.
    1 2D Structure

    Eliglustat

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(1R,2R)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]octanamide;(2R,3R)-2,3-dihydroxybutanedioic acid
    2.1.2 InChI
    InChI=1S/2C23H36N2O4.C4H6O6/c2*1-2-3-4-5-6-9-22(26)24-19(17-25-12-7-8-13-25)23(27)18-10-11-20-21(16-18)29-15-14-28-20;5-1(3(7)8)2(6)4(9)10/h2*10-11,16,19,23,27H,2-9,12-15,17H2,1H3,(H,24,26);1-2,5-6H,(H,7,8)(H,9,10)/t2*19-,23-;1-,2-/m111/s1
    2.1.3 InChI Key
    KUBARPMUNHKBIQ-VTHUDJRQSA-N
    2.1.4 Canonical SMILES
    CCCCCCCC(=O)NC(CN1CCCC1)C(C2=CC3=C(C=C2)OCCO3)O.CCCCCCCC(=O)NC(CN1CCCC1)C(C2=CC3=C(C=C2)OCCO3)O.C(C(C(=O)O)O)(C(=O)O)O
    2.1.5 Isomeric SMILES
    CCCCCCCC(=O)N[C@H](CN1CCCC1)[C@@H](C2=CC3=C(C=C2)OCCO3)O.CCCCCCCC(=O)N[C@H](CN1CCCC1)[C@@H](C2=CC3=C(C=C2)OCCO3)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    N0493335P3
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cerdelga

    2. Eliglustat

    3. Genz-112638

    2.3.2 Depositor-Supplied Synonyms

    1. Eliglustat Hemitartrate

    2. Cerdelga

    3. 928659-70-5

    4. Agalsidase Beta

    5. Eliglustat (hemitartrate)

    6. Genz-112638

    7. 104138-64-9

    8. Eliglustat Tartrate [usan]

    9. Eliglustat (tartrate)

    10. Genz 112638

    11. 928659-70-5 (tartrate)

    12. N0493335p3

    13. N-[(1r,2r)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]octanamide;(2r,3r)-2,3-dihydroxybutanedioic Acid

    14. N-((1r,2r)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)octanamide Hemi((2r,3r)-2,3-dihydroxysuccinate)

    15. Unii-n0493335p3

    16. Cerdelga (tn)

    17. Eliglustat L-tartrate

    18. Eliglustat Tartrate [mi]

    19. Chebi:83353

    20. Eliglustat Tartrate (jan/usan)

    21. Dtxsid50239166

    22. Eliglustat Tartrate [jan]

    23. Eliglustat Tartrategenz-112638

    24. Eliglustat Tartrate [who-dd]

    25. Hy-14885a

    26. Genz-112638;eliglustat Hemitartrate

    27. Cs-5423

    28. Ex-a2301-1

    29. Eliglustat Hemitartrate (genz-112638)

    30. Eliglustat Tartrate [orange Book]

    31. Ac-35333

    32. Bis(n-((1r,2r)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-hydroxy-1-(pyrrolidin-1- Ylmethyl)ethyl)octanamide) (2r,3r)-2,3-dihydroxybutanedioate

    33. Octanamide, N-((1r,2r)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-hydroxy-1-(1- Pyrrolidinylmethyl)ethyl)-, (2r,3r)-2,3-dihydroxybutanedioate (2:1)

    34. Cerdelga Component Eliglustat Tartrate

    35. S4433

    36. C16736

    37. D09894

    38. Eliglustat Tartrate Component Of Cerdelga

    39. Q27156779

    40. (1r,2r)-octanoic Acid(2-(2',3'-dihydro-benzo(1,4) Dioxin-6'-yl)-2-hydroxy-1-pyrrolidin-1-ylmethyl-ethyl)-amide-l-tartaric Acid Salt

    41. Bis{1-[(2r,3r)-3-(2,3-dihydro-1,4-benzodioxin-6-yl)-3-hydroxy-2-(octanoylamino)propyl]pyrrolidinium} (2r,3r)-2,3-dihydroxysuccinate

    42. Bis{n-[(1r,2r)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl]octanamide} (2r,3r)-2,3-dihydroxysuccinic Acid

    43. N-((1r,2r)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxy-3-(pyrrolidin-1-yl)propan-2-yl)octanamide ((2r,3r)-2,3-dihydroxysuccinate)(2:1)

    44. Octanamide, N-((1r,2r)-2-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-hydroxy-1-(1-pyrrolidinylmethyl)ethyl)-, (2r,3r)-2,3-dihydroxybutanedioate (2:1)

    2.4 Create Date
    2011-06-02
    3 Chemical and Physical Properties
    Molecular Weight 959.2 g/mol
    Molecular Formula C50H78N4O14
    Hydrogen Bond Donor Count8
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count25
    Exact Mass958.55145317 g/mol
    Monoisotopic Mass958.55145317 g/mol
    Topological Polar Surface Area257 Ų
    Heavy Atom Count68
    Formal Charge0
    Complexity617
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Indication

    Agalsidase beta is indicated in the treatment of Fabry disease.

    FDA Label

    Cerdelga is indicated for the long-term treatment of adult patients with Gaucher disease type 1 (GD1), who are CYP2D6 poor metabolisers (PMs), intermediate metabolisers (IMs) or extensive metabolisers (EMs).

    Treatment of Gaucher disease Type 1 and Type 3, Treatment of Gaucher disease Type 2

    Fabrazyme is indicated for long-term enzyme replacement therapy in patients with a confirmed diagnosis of Fabry disease (-galactosidase-A deficiency).

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Agalsidase beta is a recombinant human -galactosidase A used as enzyme replacement therapy in the treatment of Fabry disease. It has a long duration of action and a wide therapeutic index. Patients should be counselled regarding the risk of infusion related reactions and hypersensitivity.

    5.2 MeSH Pharmacological Classification

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    alpha-Glucosidases [CS]; Hydrolytic Lysosomal Neutral Glycosphingolipid-specific Enzyme [EPC]
    5.4 ATC Code

    A16AX10

    A16AB04

    A - Alimentary tract and metabolism

    A16 - Other alimentary tract and metabolism products

    A16A - Other alimentary tract and metabolism products

    A16AB - Enzymes

    A16AB04 - Agalsidase beta

    5.5 Absorption, Distribution and Excretion

    Absorption

    A 1 mg/kg dose of agalsidase beta with a mean infusion length of 115 minutes reaches a Cmax 5.0 1.1 g/mL with an AUC of 496 137 g\*min/mL.

    Route of Elimination

    After nonspecific proteolysis, the amino acids from protein drugs are reused for protein synthesis or further broken down and eliminated by the kidneys.

    Volume of Distribution

    A 1 mg/kg dose of agalsidase beta with a mean infusion length of 115 minutes has a VSS of 112 13 mL/kg.

    Clearance

    A 1 mg/kg dose of agalsidase beta with a mean infusion length of 115 minutes has a clearance of 2.1 0.7 mL/min/kg.

    5.6 Metabolism/Metabolites

    Data regarding the metabolism of agalsidase beta is not readily available. However, protein drugs are expected to be degraded by proteases and other catalytic enzymes to smaller peptides and amino acids.

    5.7 Biological Half-Life

    agalsidase beta has a half like of 67 12 min for a 1 mg/kg dose with a mean infusion length of 115 minutes.

    5.8 Mechanism of Action

    -galactosidase A is uptaken by cells via the mannose 6 phosphate receptor. Agalsidase beta hydrolyzes globotriaosylceramide and other glycosphingolipids that would normally be hydrolyzed by endogenous -galactosidase A. Preventing the accumulation of glycosphingolipids prevents or reduces the severity of manifestations of Fabry disease such as renal failure, cardiomyopathy, or cerebrovascular events.

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    13-Sep-2022
    11-Sep-2024
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