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    Sotagliflozin

    ACTIVE PHARMA INGREDIENTS

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    $ API Ref.Price (USD/KG) : 2,909Xls

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    2D Structure
    Also known as: 1018899-04-1, Lx-4211, Lx4211, Lp-802034, (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2h-pyran-3,4,5-triol, 6b4zbs263y
    Molecular Formula
    C21H25ClO5S
    Molecular Weight
    424.9  g/mol
    InChI Key
    QKDRXGFQVGOQKS-CRSSMBPESA-N
    FDA UNII
    6B4ZBS263Y
    Sotagliflozin is an orally bioavailable inhibitor of the sodium-glucose co-transporter subtype 1 (SGLT1) and 2 (SGLT2), with potential antihyperglycemic activity. Upon oral administration, sotagliflozin binds to and blocks both SGLT1 in the gastrointestinal (GI) tract and SGLT2 in the kidneys, thereby suppressing the absorption of glucose from the GI tract and the reabsorption of glucose by the proximal tubule into the bloodstream, respectively. This decreases glucose uptake and enhances the urinary excretion of glucose, which lowers and/or normalizes blood glucose levels. SGLT1 is the primary transporter responsible for glucose absorption from the GI tract. SGLT2, a transport protein exclusively expressed in the proximal renal tubules, mediates approximately 90% of renal glucose reabsorption from tubular fluid.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyloxane-3,4,5-triol
    2.1.2 InChI
    InChI=1S/C21H25ClO5S/c1-3-26-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(27-20)28-2/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1
    2.1.3 InChI Key
    QKDRXGFQVGOQKS-CRSSMBPESA-N
    2.1.4 Canonical SMILES
    CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)SC)O)O)O)Cl
    2.1.5 Isomeric SMILES
    CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)SC)O)O)O)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    6B4ZBS263Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2h-pyran-3,4,5-triol

    2. Lx-4211

    3. Lx4211

    2.3.2 Depositor-Supplied Synonyms

    1. 1018899-04-1

    2. Lx-4211

    3. Lx4211

    4. Lp-802034

    5. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2h-pyran-3,4,5-triol

    6. 6b4zbs263y

    7. Sar439954

    8. Sar-439954

    9. (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyloxane-3,4,5-triol

    10. Zynquista

    11. Beta-l-xylopyranoside, Methyl 5-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-1-thio-, (5s)-

    12. Sotagliflozin [usan:inn]

    13. Unii-6b4zbs263y

    14. Beta-l-xylopyranoside, Methyl 5-c-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-thio-, (5s)-

    15. Mfcd22493506

    16. Lx 4211

    17. Lp 802034

    18. Sotagliflozin [mi]

    19. Sotagliflozin (lx4211)

    20. Sotagliflozin [inn]

    21. Sotagliflozin (usan/inn)

    22. Sotagliflozin [usan]

    23. Sotagliflozin (lx-4211)

    24. Sotagliflozin [who-dd]

    25. Gtpl8312

    26. Schembl1038287

    27. Chembl3039507

    28. Dtxsid20144314

    29. Amy12393

    30. Ex-a1167

    31. Bdbm50235017

    32. S8103

    33. Zinc95641922

    34. Akos025290846

    35. Ccg-268940

    36. Cs-1069

    37. Db12713

    38. Ac-29890

    39. As-35202

    40. Bl161424

    41. Hy-15516

    42. D10669

    43. A852129

    44. Q27088840

    45. (2s,3r,4r,5s,6r)-2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-tetrahydro-6-(methylthio)-2h-pyran-3,4,5-triol;lx4211

    46. (2s,3r,4r,5s,6r)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2h-pyran-3,4,5-triol

    47. .beta.-l-xylopyranoside, Methyl 5-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-1-thio-, (5s)-

    48. Methyl (5s)-5-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-1-thio-.beta.-l-xylopyranoside

    2.4 Create Date
    2008-07-07
    3 Chemical and Physical Properties
    Molecular Weight 424.9 g/mol
    Molecular Formula C21H25ClO5S
    XLogP33.2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass424.1111228 g/mol
    Monoisotopic Mass424.1111228 g/mol
    Topological Polar Surface Area104 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity476
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    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

    Zynquista is indicated as an adjunct to insulin therapy to improve glycaemic control in adults with type 1 diabetes mellitus with a Body Mass Index (BMI) 27 kg/m2, who have failed to achieve adequate glycaemic control despite optimal insulin therapy.

    Treatment of type II diabetes mellitus

    Treatment of type I diabetes mellitus

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 ATC Code

    A10

    A - Alimentary tract and metabolism

    A10 - Drugs used in diabetes

    A10B - Blood glucose lowering drugs, excl. insulins

    A10BK - Sodium-glucose co-transporter 2 (sglt2) inhibitors

    A10BK06 - Sotagliflozin