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    Chemistry

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    Also known as: 72599-27-0, N-butyldeoxynojirimycin, Zavesca, Butyldeoxynojirimycin, Nb-dnj, N-butylmoranoline
    Molecular Formula
    C10H21NO4
    Molecular Weight
    219.28  g/mol
    InChI Key
    UQRORFVVSGFNRO-UTINFBMNSA-N
    FDA UNII
    ADN3S497AZ
    Miglustat
    Miglustat is a synthetic, N-alkylated imino analogue of D-glucose. Miglustat competitively and reversibly binds to and inhibits the activity of UDP-glucose ceramide glucosyltransferase, which catalyzes the initial step in the synthesis of glycosphingolipids (GSL). This leads to a decrease in the production of glycosphingolipid, which has important roles in various cellular processes. Miglustat can be used in substrate reduction therapy in diseases in which the enzyme glucocerebrosidase, that is responsible for the breakdown of GSL, is deficient.
    Miglustat is a Glucosylceramide Synthase Inhibitor. The mechanism of action of miglustat is as a Glucosylceramide Synthase Inhibitor.
    1 2D Structure

    Miglustat

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R,3R,4R,5S)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol
    2.1.2 InChI
    InChI=1S/C10H21NO4/c1-2-3-4-11-5-8(13)10(15)9(14)7(11)6-12/h7-10,12-15H,2-6H2,1H3/t7-,8+,9-,10-/m1/s1
    2.1.3 InChI Key
    UQRORFVVSGFNRO-UTINFBMNSA-N
    2.1.4 Canonical SMILES
    CCCCN1CC(C(C(C1CO)O)O)O
    2.1.5 Isomeric SMILES
    CCCCN1C[C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    ADN3S497AZ
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Butyldeoxynojirimycin

    2. N-(n-butyl)deoxy-nojirimycin

    3. N-(n-butyl)deoxynojirimycin

    4. N-butyl Deoxynojirimycin

    5. N-butyldeoxynojirimycin

    6. Ogt 918

    7. Ogt-918

    8. Sc 48334

    9. Sc-48334

    10. Zavesca

    2.3.2 Depositor-Supplied Synonyms

    1. 72599-27-0

    2. N-butyldeoxynojirimycin

    3. Zavesca

    4. Butyldeoxynojirimycin

    5. Nb-dnj

    6. N-butylmoranoline

    7. (2r,3r,4r,5s)-1-butyl-2-(hydroxymethyl)piperidine-3,4,5-triol

    8. N-butyl-1-deoxynojirimycin

    9. Budnj

    10. N-butyl Deoxynojirimycin

    11. N-(n-butyl)deoxynojirimycin

    12. Ogt 918

    13. Sc-48334

    14. Ogt-918

    15. N-butyl-dnj

    16. Sc 48334

    17. 3,4,5-piperidinetriol, 1-butyl-2-(hydroxymethyl)-, (2r,3r,4r,5s)-

    18. N-butyldeoxynojirimycin.hcl

    19. Adn3s497az

    20. Chembl1029

    21. Chebi:50381

    22. 72599-27-0 (free Base)

    23. N-butyl Dnj

    24. Miglustat [usan]

    25. Dsstox_cid_25618

    26. Dsstox_rid_81006

    27. Dsstox_gsid_45618

    28. Miglustatum

    29. Vevesca

    30. Zavesca (tn)

    31. Cas-72599-27-0

    32. N-bu-dnj

    33. N-butyl-deoxynojirimycin

    34. Nbv

    35. Unii-adn3s497az

    36. Sc48334

    37. Brazaves

    38. N-(n-butyl)deoxy-nojirimycin

    39. Miglustat [usan:inn:ban]

    40. D-glucitol, 1,5-(butylimino)-1,5-dideoxy-

    41. Ncgc00018140-02

    42. Brazaves (tn)

    43. Mfcd00272581

    44. Miglustat [inn]

    45. Miglustat [jan]

    46. Miglustat [mi]

    47. 1,5-dideoxy-1,5-n-butylimino-d-glucitol

    48. Miglustat [vandf]

    49. Miglustat [mart.]

    50. Miglustat [who-dd]

    51. N-(n-butyl)-1,5-dideoxy-1,5-imino-d-glucitol

    52. Miglustat [ema Epar]

    53. Miglustat (jan/usan/inn)

    54. Schembl246893

    55. Ogt918n-butyldeoxynojirimycin

    56. Gtpl4841

    57. Ogt918

    58. Miglustat [orange Book]

    59. Dtxsid6045618

    60. Bdbm18355

    61. Hms2090n20

    62. Zinc3794711

    63. Tox21_110830

    64. Akos028109118

    65. Tox21_110830_1

    66. Db00419

    67. 3,4,5-piperidinetriol, 1-butyl-2-(hydroxymethyl)-, (2r-(2alpha,3beta,4alpha,5beta))-

    68. Ncgc00024452-03

    69. Ncgc00024452-04

    70. Hy-17020

    71. N-(n-butyl)-1-deoxynojirimycin Min. 99%

    72. N-butyldeoxynojirimycin, Film (dried In Situ)

    73. D05032

    74. P16976

    75. Ab00489939-10

    76. 1,5-(butylimino)-1,5 Dideoxy,d-glucitol

    77. A850985

    78. Q425911

    79. Sr-01000000043

    80. Sr-01000000043-2

    81. W-203639

    82. 1,5-(butylimino)-1,5-dideoxy-d-glucitol(2r,3r,4r,5s)-1-butyl-2-(hydroxymethyl)-3,4,5-piperidinetriol

    83. 134282-77-2

    2.4 Create Date
    2005-06-29
    3 Chemical and Physical Properties
    Molecular Weight 219.28 g/mol
    Molecular Formula C10H21NO4
    XLogP3-0.6
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass219.14705815 g/mol
    Monoisotopic Mass219.14705815 g/mol
    Topological Polar Surface Area84.2 Ų
    Heavy Atom Count15
    Formal Charge0
    Complexity190
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    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 NameZavesca
    PubMed HealthMiglustat (By mouth)
    Drug ClassesEndocrine-Metabolic Agent
    Drug LabelZavesca (miglustat capsules, 100 mg) is an inhibitor of the enzyme glucosylceramide synthase, which is a glucosyl transferase enzyme responsible for the first step in the synthesis of most glycosphingolipids. Zavesca is an N-alkylated imino sugar, a...
    Active IngredientMiglustat
    Dosage FormCapsule
    RouteOral
    Strength100mg
    Market StatusPrescription
    CompanyActelion Pharms

    2 of 2  
    Drug NameZavesca
    PubMed HealthMiglustat (By mouth)
    Drug ClassesEndocrine-Metabolic Agent
    Drug LabelZavesca (miglustat capsules, 100 mg) is an inhibitor of the enzyme glucosylceramide synthase, which is a glucosyl transferase enzyme responsible for the first step in the synthesis of most glycosphingolipids. Zavesca is an N-alkylated imino sugar, a...
    Active IngredientMiglustat
    Dosage FormCapsule
    RouteOral
    Strength100mg
    Market StatusPrescription
    CompanyActelion Pharms

    4.2 Drug Indication

    For the treatment of adult patients with mild to moderate type 1 (nonneuropathic) Gaucher's disease for whom enzyme replacement therapy is not a therapeutic option (e.g. due to constraints such as allergy, hypersensitivity, or poor venous access). Now approved in some countries for the treatment of progressive neurological symptoms in adult and pediatric patients with Niemann-Pick disease type C (NP-C).

    FDA Label

    Miglustat Gen. Orph is indicated for the oral treatment of adult patients with mild to moderate type 1 Gaucher disease.

    Miglustat Gen. Orph may be used only in the treatment of patients for whom enzyme replacement therapy is unsuitable.

    Miglustat Gen. Orph is indicated for the treatment of progressive neurological manifestations in adult patients and paediatric patients with Niemann-Pick type C disease.

    Yargesa is indicated for the oral treatment of adult patients with mild to moderate type 1 Gaucher disease.

    Yargesa may be used only in the treatment of patients for whom enzyme replacement therapy is unsuitable.

    Yargesa is indicated for the treatment of progressive neurological manifestations in adult patients and paediatric patients with Niemann-Pick type C disease.

    Zavesca is indicated for the oral treatment of adult patients with mild to moderate type-1 Gaucher disease. Zavesca may be used only in the treatment of patients for whom enzyme replacement therapy is unsuitable.

    Zavesca is indicated for the treatment of progressive neurological manifestations in adult patients and paediatric patients with Niemann-Pick type-C disease.

    Miglustat Dipharma is indicated for the oral treatment of adult patients with mild to moderate type 1 Gaucher disease.

    Miglustat Dipharma may be used only in the treatment of patients for whom enzyme replacement therapy is unsuitable.

    Miglustat Dipharma is indicated for the treatment of progressive neurological manifestations in adult patients and paediatric patients with Niemann-Pick type C disease.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Miglustat, an N-alkylated imino sugar, is a synthetic analogue of D-glucose. Miglustat is an inhibitor of the enzyme glucosylceramide synthase, which is a glucosyl transferase enzyme responsible for catalyzing the formation of glucosylceramide (glucocerebroside). Glucosylceramide is a substrate for the endogenous glucocerebrosidase, an enzyme that is deficient in Gaucher's disease. The accumulation of glucosylceramide due to the absence of glucocerebrosidase results in the storage of this material in the lysosomes of tissue macrophages, leading to widespread pathology due to infiltration of lipid-engorged macrophages in the viscera, lymph nodes, and bone marrow. This results in secondary hematologic consequences including sever anemia and thrombocytopenia, in addition to the characteristic progressive hepatosplenomegaly, as well as skeletal complications including osteonecrosis and osteopenia with secondary pathological fractures.

    5.2 MeSH Pharmacological Classification

    Anti-HIV Agents

    Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

    Glycoside Hydrolase Inhibitors

    Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. (See all compounds classified as Glycoside Hydrolase Inhibitors.)

    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 Active Moiety
    MIGLUSTAT
    5.3.2 FDA UNII
    ADN3S497AZ
    5.3.3 Pharmacological Classes
    Glucosylceramide Synthase Inhibitors [MoA]; Glucosylceramide Synthase Inhibitor [EPC]
    5.4 ATC Code

    A16AX06

    A16AX06

    A16AX06

    A16AX06

    A16AX06

    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

    A - Alimentary tract and metabolism

    A16 - Other alimentary tract and metabolism products

    A16A - Other alimentary tract and metabolism products

    A16AX - Various alimentary tract and metabolism products

    A16AX06 - Miglustat

    5.5 Absorption, Distribution and Excretion

    Absorption

    Mean oral bioavailability is 97%.

    5.6 Metabolism/Metabolites

    There is no evidence that miglustat is metabolized in humans.

    5.7 Biological Half-Life

    The effective half-life of miglustat is approximately 6 to 7 hours.

    5.8 Mechanism of Action

    Miglustat functions as a competitive and reversible inhibitor of the enzyme glucosylceramide synthase, the initial enzyme in a series of reactions which results in the synthesis of most glycosphingolipids. The goal of treatment with miglustat is to reduce the rate of glycosphingolipid biosynthesis so that the amount of glycosphingolipid substrate is reduced to a level which allows the residual activity of the deficient glucocerebrosidase enzyme to be more effective (substrate reduction therapy), reducing the accumulation of glucocerebroside in macrophages. In vitro and in vivo studies have shown that miglustat can reduce the synthesis of glucosylceramide-based glycosphingolipids. In clinical trials, miglustat improved liver and spleen volume, as well as hemoglobin concentration and platelet count. Inhibition of glycosphingolipid synthesis has also shown to reduce intracellular lipid storage, improve fluid-phase endosomal uptake and normalize lipid transport in peripheral blood B lymphocytes of NP-C patients, which results in a decrease in the potentially neurotoxic accumulation of gnagliosides GM2 and GM3, lactosylceramide and glucosylceramide, possibly preventing further neuronal damage. Other studies have also suggested that miglustat may indirectly modulate intracellular calcium homeostasis through its effects on glucosylceramide levels, and evidence has shown that an initiating factor in the pathogenesis of NP-C may be impaired calcium homeostasis related to sphingosine storage. Therefore, the effect that miglustat exerts on intracellular calcium levels may influence an important underlying pathogenic mechanism of NP-C.

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    08-Feb-2021
    24-Jun-2024
    KGS
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