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    Vildagliptin

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Vildagliptin, 274901-16-5, (2r)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile, Vildagliptin (2r)-isomer, Schembl671629, Dtxsid301119534
    Molecular Formula
    C17H25N3O2
    Molecular Weight
    303.4  g/mol
    InChI Key
    SYOKIDBDQMKNDQ-JULPFRMLSA-N
    A pyrrolidine-carbonitrile derivative and potent inhibitor of DIPEPTIDYL PEPTIDASE 4 that is used in the treatment of TYPE 2 DIABETES MELLITUS.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile
    2.1.2 InChI
    InChI=1S/C17H25N3O2/c18-9-14-2-1-3-20(14)15(21)10-19-16-5-12-4-13(6-16)8-17(22,7-12)11-16/h12-14,19,22H,1-8,10-11H2/t12?,13?,14-,16?,17?/m1/s1
    2.1.3 InChI Key
    SYOKIDBDQMKNDQ-JULPFRMLSA-N
    2.1.4 Canonical SMILES
    C1CC(N(C1)C(=O)CNC23CC4CC(C2)CC(C4)(C3)O)C#N
    2.1.5 Isomeric SMILES
    C1C[C@@H](N(C1)C(=O)CNC23CC4CC(C2)CC(C4)(C3)O)C#N
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. (2s)-(((3-hydroxyadamantan-1-yl)amino)acetyl)pyrrolidine-2-carbonitrile

    2. Galvus

    3. Nvp Laf237

    4. Nvp-laf237

    5. Vildagliptin

    2.2.2 Depositor-Supplied Synonyms

    1. Vildagliptin

    2. 274901-16-5

    3. (2r)-1-[2-[(3-hydroxy-1-adamantyl)amino]acetyl]pyrrolidine-2-carbonitrile

    4. Vildagliptin (2r)-isomer

    5. Schembl671629

    6. Dtxsid301119534

    7. Akos015969326

    8. F78360

    9. A819091

    10. (2r)-1-[2-[(3-hydroxy-1-adamantyl)amino]-1-oxoethyl]-2-pyrrolidinecarbonitrile

    11. (2r)-1-[2-[(3-oxidanyl-1-adamantyl)amino]ethanoyl]pyrrolidine-2-carbonitrile

    12. (2r)-1-[2-[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-2-pyrrolidine Carbonitrile; (r)-1-(2-(((1r,3s,5r,7s)-3-hydroxyadamantan-1-yl)amino)acetyl)pyrrolidine-2-carbonitrile

    13. Rel-(2r)-1-[2-[(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)amino]acetyl]-2-pyrrolidinecarbonitrile

    2.2.3 Other Synonyms

    1. Jalra

    2. Equa

    2.3 Create Date
    2008-07-11
    3 Chemical and Physical Properties
    Molecular Weight 303.4 g/mol
    Molecular Formula C17H25N3O2
    XLogP30.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass303.19467705 g/mol
    Monoisotopic Mass303.19467705 g/mol
    Topological Polar Surface Area76.4 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity523
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count2
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Vildagliptin is indicated as an adjunct to diet and exercise to improve glycaemic control in adults with type 2 diabetes mellitus:

    as monotherapy in patients in whom metformin is inappropriate due to contraindications or intolerance. in combination with other medicinal products for the treatment of diabetes, including insulin, when these do not provide adequate glycaemic control

    Vildagliptin is indicated as an adjunct to diet and exercise to improve glycaemic control in adults with type 2 diabetes mellitus:

    - as monotherapy in patients in whom metformin is inappropriate due to contraindications or intolerance.

    - in combination with other medicinal products for the treatment of diabetes, including insulin, when these do not provide adequate glycaemic control (see sections 4. 4, 4. 5 and 5. 1 for available data on different combinations).

    Vildagliptin is indicated as an adjunct to diet and exercise to improve glycaemic control in adults with type 2 diabetes mellitus:

    - as monotherapy in patients in whom metformin is inappropriate due to contraindications or intolerance.

    - in combination with other medicinal products for the treatment of diabetes, including insulin, when these do not provide adequate glycaemic control (see sections 4. 4, 4. 5 and 5. 1 for available data on different combinations).

    Treatment of type II diabetes mellitus

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Dipeptidyl-Peptidase IV Inhibitors

    Compounds that suppress the degradation of INCRETINS by blocking the action of DIPEPTIDYL-PEPTIDASE IV. This helps to correct the defective INSULIN and GLUCAGON secretion characteristic of TYPE 2 DIABETES MELLITUS by stimulating insulin secretion and suppressing glucagon release. (See all compounds classified as Dipeptidyl-Peptidase IV Inhibitors.)

    Hypoglycemic Agents

    Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)

    5.2 ATC Code

    A10BH02

    A10BH02

    A10BH02

    A - Alimentary tract and metabolism

    A10 - Drugs used in diabetes

    A10B - Blood glucose lowering drugs, excl. insulins

    A10BH - Dipeptidyl peptidase 4 (dpp-4) inhibitors

    A10BH02 - Vildagliptin