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    Dapagliflozin Propanediol

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    2D Structure
    Also known as: 960404-48-2, Dapagliflozin propanediol monohydrate, Dapagliflozin propanediol hydrate, Farxiga, Dapagliflozin ((2s)-1,2-propanediol, hydrate), Bms-512148-05
    Molecular Formula
    C24H35ClO9
    Molecular Weight
    503.0  g/mol
    InChI Key
    GOADIQFWSVMMRJ-UPGAGZFNSA-N
    FDA UNII
    887K2391VH
    Dapagliflozin Propanediol is the propanediol form of dapagliflozin, a selective sodium-glucose co-transporter subtype 2 (SGLT2) inhibitor with antihyperglycemic activity. Upon administration, dapagliflozin selectively targets and inhibits SGLT2, thereby preventing the reabsorption of glucose by the kidneys.
    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-(hydroxymethyl)oxane-3,4,5-triol;(2S)-propane-1,2-diol;hydrate
    2.1.2 InChI
    InChI=1S/C21H25ClO6.C3H8O2.H2O/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21;1-3(5)2-4;/h3-8,10,17-21,23-26H,2,9,11H2,1H3;3-5H,2H2,1H3;1H2/t17-,18-,19+,20-,21+;3-;/m10./s1
    2.1.3 InChI Key
    GOADIQFWSVMMRJ-UPGAGZFNSA-N
    2.1.4 Canonical SMILES
    CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)CO)O)O)O)Cl.CC(CO)O.O
    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)CO)O)O)O)Cl.C[C@@H](CO)O.O
    2.2 Other Identifiers
    2.2.1 UNII
    887K2391VH
    2.3 Synonyms
    2.3.1 MeSH Synonyms

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

    2. 2-(3-(4-ethoxybenzyl)-4-chlorophenyl)-6-hydroxymethyltetrahydro-2h-pyran-3,4,5-triol

    3. Bms 512148

    4. Bms-512148

    5. Bms512148

    6. Dapagliflozin

    7. Farxiga

    8. Forxiga

    2.3.2 Depositor-Supplied Synonyms

    1. 960404-48-2

    2. Dapagliflozin Propanediol Monohydrate

    3. Dapagliflozin Propanediol Hydrate

    4. Farxiga

    5. Dapagliflozin ((2s)-1,2-propanediol, Hydrate)

    6. Bms-512148-05

    7. Dapagliflozin S-propylene Glycol Monohydrate

    8. Dapagliflozin Propylene Glycolate Hydrate

    9. Chebi:85079

    10. Dapagliflozin Propanediol [usan]

    11. Dapagliflozin Mixture With Propylene Glycol, Hydrate

    12. 887k2391vh

    13. (2s,3r,4r,5s,6r)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol;(2s)-propane-1,2-diol;hydrate

    14. Dapagliflozin [usan:inn]

    15. Dapagliflozin Propylene Glycol Hydrate

    16. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol Compound With (s)-propane-1,2-diol (1:1) Hydrate

    17. D-glucitol, 1,5-anhydro-1-c-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-, (1s)-, Compd. With (2s)-1,2-propanediol, Hydrate (1:1:1)

    18. Unii-887k2391vh

    19. Dapagliflozin Propylene Glycolate Hydrate [jan]

    20. Dapagliflozin (s)-propylene Glycol Hydrate

    21. Chembl2103802

    22. Dtxsid00914678

    23. Ex-a2824

    24. Dapagliflozin Propylene Glycol

    25. Hy-10450a

    26. Mfcd28167768

    27. S5566

    28. Akos027250601

    29. Ccg-269711

    30. Ac-29230

    31. As-64915

    32. Dapagliflozin (2s)-1,2-propanediol Hydrate

    33. F20667

    34. Bms-512148 (2s)-1,2-propanediol, Hydrate

    35. Dapagliflozin (2s)-1,2-propanediol Monohydrate

    36. Xigduo Component Dapagliflozin Propanediol

    37. A900162

    38. Dapagliflozin Propanediol Component Of Xigduo

    39. Dapagliflozin Propanediol Monohydrate [who-dd]

    40. Q27158320

    41. Dapagliflozin Propanediol Monohydrate [ema Epar]

    42. Dapagliflozin Compound With (2s)-1,2-propanediol Hydrate

    43. Dapagliflozin Compound With (2s)-1,2-propanediol Hydrate [mi]

    44. (2s)-propane-1,2-diol (2s,3r,4r,5s,6r)-2-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-6-(hydroxymethyl)oxane-3,4,5-triol Hydrate

    45. (2s)-propane-1,2-diol--(1s)-1,5-anhydro-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-d-glucitol--water (1/1/1)

    46. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro- 2h-pyran-3,4,5-triol, (2s)-propane-1,2-diol (1:1) Monohydrate

    47. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol (s)-propane-1,2-diol Hydrate

    48. (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol, (2s)-propane-1,2-diol (1:1) Monohydrate

    49. 1700615-13-9

    2.4 Create Date
    2008-09-29
    3 Chemical and Physical Properties
    Molecular Weight 503.0 g/mol
    Molecular Formula C24H35ClO9
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count7
    Exact Mass502.1969604 g/mol
    Monoisotopic Mass502.1969604 g/mol
    Topological Polar Surface Area141 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity493
    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

    Forxiga is indicated in adults and children aged 10 years and above for the treatment of insufficiently controlled type 2 diabetes mellitus as an adjunct to diet and exercise

    - as monotherapy when metformin is considered inappropriate due to intolerance.

    - in addition to other medicinal products for the treatment of type 2 diabetes.

    For study results with respect to combination of therapies, effects on glycaemic control, cardiovascular and renal events, and the populations studied.

    Heart failure

    - Forxiga is indicated in adults for the treatment of symptomatic chronic heart failure with reduced ejection fraction.

    Chronic kidney disease

    - Forxiga is indicated in adults for the treatment of chronic kidney disease.

    Type 2 diabetes mellitus

    Edistride is indicated in adults and children aged 10 years and above for the treatment of insufficiently controlled type 2 diabetes mellitus as an adjunct to diet and exercise

    - as monotherapy when metformin is considered inappropriate due to intolerance.

    - in addition to other medicinal products for the treatment of type 2 diabetes.

    For study results with respect to combination of therapies, effects on glycaemic control, cardiovascular and renal events, and the populations studied, see sections 4. 4, 4. 5 and 5. 1.

    Heart failure

    Edistride is indicated in adults for the treatment of symptomatic chronic heart failure with reduced ejection fraction.

    Chronic kidney disease

    Edistride is indicated in adults for the treatment of chronic kidney disease.

    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

    A10BK01

    A10BK01