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    Remogliflozin Etabonate

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    2D Structure
    Also known as: 442201-24-3, Gsk-189075, Gsk-189075a, Gsk189075a, Remogliflozin etabonate [inn], Tr0qt6qsul
    Molecular Formula
    C26H38N2O9
    Molecular Weight
    522.6  g/mol
    InChI Key
    UAOCLDQAQNNEAX-ABMICEGHSA-N
    FDA UNII
    TR0QT6QSUL
    Remogliflozin Etabonate is an orally available prodrug of remogliflozin, a benzylpyrazole glucoside-based inhibitor of renal sodium-glucose co-transporter subtype 2 (SGLT2) with antihyperglycemic activity. Upon administration and absorption, the inactive prodrug is converted to its active form remogliflozin and acts selectively on the sodium-glucose co-transporter subtype 2 (SGLT2).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    ethyl [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-methyl-1-propan-2-yl-4-[(4-propan-2-yloxyphenyl)methyl]pyrazol-3-yl]oxyoxan-2-yl]methyl carbonate
    2.1.2 InChI
    InChI=1S/C26H38N2O9/c1-7-33-26(32)34-13-20-21(29)22(30)23(31)25(36-20)37-24-19(16(6)28(27-24)14(2)3)12-17-8-10-18(11-9-17)35-15(4)5/h8-11,14-15,20-23,25,29-31H,7,12-13H2,1-6H3/t20-,21-,22+,23-,25+/m1/s1
    2.1.3 InChI Key
    UAOCLDQAQNNEAX-ABMICEGHSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)OCC1C(C(C(C(O1)OC2=NN(C(=C2CC3=CC=C(C=C3)OC(C)C)C)C(C)C)O)O)O
    2.1.5 Isomeric SMILES
    CCOC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=NN(C(=C2CC3=CC=C(C=C3)OC(C)C)C)C(C)C)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    TR0QT6QSUL
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(4-isopropoxybenzyl)-1-isopropyl-5-methyl-1h-pyrazol-3-yl 6-o-(ethoxycarbonyl)-beta-d-glucopyranoside

    2.3.2 Depositor-Supplied Synonyms

    1. 442201-24-3

    2. Gsk-189075

    3. Gsk-189075a

    4. Gsk189075a

    5. Remogliflozin Etabonate [inn]

    6. Tr0qt6qsul

    7. Ethyl (((2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-((4-(4-isopropoxybenzyl)-1-isopropyl-5-methyl-1h-pyrazol-3-yl)oxy)tetrahydro-2h-pyran-2-yl)methyl) Carbonate

    8. Ethyl [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[5-methyl-1-propan-2-yl-4-[(4-propan-2-yloxyphenyl)methyl]pyrazol-3-yl]oxyoxan-2-yl]methyl Carbonate

    9. 5-methyl-4-(4-(1-methylethoxy)benzyl)-1-(1-methylethyl)-1h-pyrazol-3-yl 6-o-(ethoxycarbonyl)-beta-d-glucopyranoside

    10. Unii-tr0qt6qsul

    11. Kgt-1681

    12. Remogliflozin Etabonate [usan]

    13. Beta-d-glucopyranoside, 5-methyl-4-((4-(1-methylethoxy)phenyl)methyl)-1-(1-methylethyl)-1h-pyrazol-3-yl, 6-(ethyl Carbonate)

    14. Beta-d-glucopyranoside, 5-methyl-4-[[4-(1-methylethoxy)phenyl]methyl]-1-(1-methylethyl)-1h-pyrazol-3-yl, 6-(ethyl Carbonate)

    15. S0993

    16. Schembl721678

    17. Chembl2028665

    18. Dtxsid50963191

    19. Chebi:177541

    20. Gsk 189075a

    21. Zinc3979756

    22. Remogliflozin Etabonate (usan/inn)

    23. Bdbm50559516

    24. Gsk189075

    25. Bhv-091009

    26. Db12935

    27. Remogliflozin Etabonate (gsk189075)

    28. Remogliflozin Etabonate [who-dd]

    29. Br162756

    30. Hy-14945

    31. Cs-0003650

    32. D10055

    33. Q7312052

    34. 3-(6-o-ethoxycarbonyl-beta-d-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)-methyl]-1-isopropyl-5-methylpyrazole

    35. 3-(6-o-ethoxycarbonyl-beta-d-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole

    36. 4-(4-isopropoxybenzyl)-1-isopropyl-5-methyl-1h-pyrazole-3-yl 6-o-(ethoxycarbonyl)-beta-d-glucopyranoside

    37. 5-methyl-1-(propan-2-yl)-4-((4-((propan-2-yl)oxy)phenyl)methyl)-1h-pyrazol-3-yl 6-o-(ethoxycarbonyl)-.beta.-d-glucopyranoside

    38. 5-methyl-4-(4-(1-methylethoxy)benzyl)-1-(1-methylethyl)-1h-pyrazol-3-yl 6-o- (ethoxycarbonyl)-.beta.-d-glucopyranoside

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 522.6 g/mol
    Molecular Formula C26H38N2O9
    XLogP33
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count12
    Exact Mass522.25773079 g/mol
    Monoisotopic Mass522.25773079 g/mol
    Topological Polar Surface Area142 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity704
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Sodium-Glucose Transporter 2 Inhibitors

    Compounds that inhibit SODIUM-GLUCOSE TRANSPORTER 2. They lower blood sugar by preventing the reabsorption of glucose by the kidney and are used in the treatment of TYPE 2 DIABETES MELLITUS. (See all compounds classified as Sodium-Glucose Transporter 2 Inhibitors.)