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    Volixibat

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 1025216-57-2, Sar-548304 free acid, X2jz0451h8, N-(3-o-benzyl-6-o-sulfo-beta-d-glucopyranosyl)-n'-{3-[(3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1h-1lambda6-benzothiepin-5-yl]phenyl}urea, Volixibat [usan:inn], Unii-x2jz0451h8
    Molecular Formula
    C38H51N3O12S2
    Molecular Weight
    806.0  g/mol
    InChI Key
    ULVBLFBUTQMAGZ-RTNCXNSASA-N
    FDA UNII
    X2JZ0451H8
    Volixibat, also known as SHP626 or LUM002, is an investigational drug that will potentially be used for the treatment of Non-Alcoholic Steatohepatitis (NASH). If approved for use, it will be the first available agent for the treatment of NASH. Volixibat is a selective inhibitor of the apical sodium-dependent bile acid transporter (ASBT), a transmembrane protein primarily expressed by enterocytes of the ileum. Also known as the ileal bile acid transporter (IBAT), ASBT is primarily responsible for the enterohepatic recirculation of bile acids and ultimately for hepatic lipid and glucose metabolism. Inhibiting this enzyme results in a decrease of bile acids returning to the liver, which is helpful for the treatment of NASH as abnormal cholesterol metabolism and accumulation of free cholesterol in the liver have been implicated in its pathogenesis. According to Shire, the pharmaceutical manufacturer of Volixibat, it has been granted fast track status by the Food and Drug Administration due to promising initial results and a need for therapeutic treatments for NASH.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2R,3R,4S,5R,6R)-6-[[3-[(3S,4R,5R)-3-butyl-7-(dimethylamino)-3-ethyl-4-hydroxy-1,1-dioxo-4,5-dihydro-2H-16-benzothiepin-5-yl]phenyl]carbamoylamino]-3,5-dihydroxy-4-phenylmethoxyoxan-2-yl]methyl hydrogen sulfate
    2.1.2 InChI
    InChI=1S/C38H51N3O12S2/c1-5-7-18-38(6-2)23-54(46,47)30-17-16-27(41(3)4)20-28(30)31(35(38)44)25-14-11-15-26(19-25)39-37(45)40-36-33(43)34(51-21-24-12-9-8-10-13-24)32(42)29(53-36)22-52-55(48,49)50/h8-17,19-20,29,31-36,42-44H,5-7,18,21-23H2,1-4H3,(H2,39,40,45)(H,48,49,50)/t29-,31-,32-,33-,34+,35-,36-,38-/m1/s1
    2.1.3 InChI Key
    ULVBLFBUTQMAGZ-RTNCXNSASA-N
    2.1.4 Canonical SMILES
    CCCCC1(CS(=O)(=O)C2=C(C=C(C=C2)N(C)C)C(C1O)C3=CC(=CC=C3)NC(=O)NC4C(C(C(C(O4)COS(=O)(=O)O)O)OCC5=CC=CC=C5)O)CC
    2.1.5 Isomeric SMILES
    CCCC[C@@]1(CS(=O)(=O)C2=C(C=C(C=C2)N(C)C)[C@H]([C@H]1O)C3=CC(=CC=C3)NC(=O)N[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COS(=O)(=O)O)O)OCC5=CC=CC=C5)O)CC
    2.2 Other Identifiers
    2.2.1 UNII
    X2JZ0451H8
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Lum002

    2. Shp626

    2.3.2 Depositor-Supplied Synonyms

    1. 1025216-57-2

    2. Sar-548304 Free Acid

    3. X2jz0451h8

    4. N-(3-o-benzyl-6-o-sulfo-beta-d-glucopyranosyl)-n'-{3-[(3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-4-hydroxy-1,1-dioxo-2,3,4,5-tetrahydro-1h-1lambda6-benzothiepin-5-yl]phenyl}urea

    5. Volixibat [usan:inn]

    6. Unii-x2jz0451h8

    7. Starbld0000127

    8. Volixibat [inn]

    9. Volixibat [usan]

    10. Volixibat [who-dd]

    11. Chembl3707222

    12. Schembl12196537

    13. Dtxsid001098929

    14. Db13914

    15. Urea, N-(3-((3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-2,3,4,5-tetrahydro-4-hydroxy-1,1-dioxido-1-benzothiepin-5-yl)phenyl)-n'-(3-o-(phenylmethyl)-6-o-sulfo-beta-d-glucopyranosyl)-

    16. Hy-101190

    17. Cs-0020958

    18. Q27293432

    19. [(2r,3r,4s,5r,6r)-6-[[3-[(3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-4-hydroxy-1,1-dioxo-4,5-dihydro-2h-1lambda6-benzothiepin-5-yl]phenyl]carbamoylamino]-3,5-dihydroxy-4-phenylmethoxyoxan-2-yl]methyl Hydrogen Sulfate

    20. N-[3-[(3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-2,3,4,5-tetrahydro-4-hydroxy-1,1-dioxido-1-benzothiepin-5-yl]phenyl]-n'-[3-o-(phenylmethyl)-6-o-sulfo-beta-d-glucopyranosyl]urea

    21. Urea, N-(3-((3s,4r,5r)-3-butyl-7-(dimethylamino)-3-ethyl-2,3,4,5-tetrahydro-4-hydroxy-1,1-dioxido-1-benzothiepin-5-yl)phenyl)-n'-(3-o-(phenylmethyl)-6-o-sulfo-.beta.-d-glucopyranosyl)-

    2.4 Create Date
    2008-10-27
    3 Chemical and Physical Properties
    Molecular Weight 806.0 g/mol
    Molecular Formula C38H51N3O12S2
    XLogP33.1
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count14
    Exact Mass805.29141642 g/mol
    Monoisotopic Mass805.29141642 g/mol
    Topological Polar Surface Area238 Ų
    Heavy Atom Count55
    Formal Charge0
    Complexity1450
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    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

    Volixibat is an investigational drug that has not been approved for use in any conditions.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Lipid Regulating Agents

    Substances that alter the metabolism of LIPIDS. (See all compounds classified as Lipid Regulating Agents.)

    5.2 Mechanism of Action

    Volixibat is a selective inhibitor of the apical sodium-dependent bile acid transporter (ASBT), a transmembrane protein primarily expressed by enterocytes of the ileum. ASBT is primarily responsible for the recirculation of bile acids and therefore for hepatic lipid and glucose metabolism. Inhibiting this enzyme results in a decrease of bile acids returning to the liver, which is helpful for the treatment of NASH as abnormal cholesterol metabolism and accumulation of free cholesterol in the liver have been implicated in its pathogenesis.