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    Chemistry

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    Also known as: 850649-62-6, Nesina, Syr 322, Syr-322, Alogliptin (benzoate), (r)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)methyl)benzonitrile benzoate
    Molecular Formula
    C25H27N5O4
    Molecular Weight
    461.5  g/mol
    InChI Key
    KEJICOXJTRHYAK-XFULWGLBSA-N
    FDA UNII
    EEN99869SC
    Alogliptin Benzoate
    Alogliptin Benzoate is the benzoate salt form of alogliptin, a selective, orally bioavailable, pyrimidinedione-based inhibitor of dipeptidyl peptidase 4 (DPP-4), with hypoglycemic activity. In addition to its effect on glucose levels, alogliptin may inhibit inflammatory responses by preventing the toll-like receptor 4 (TLR-4)-mediated formation of proinflammatory cytokines.
    1 2D Structure

    Alogliptin Benzoate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[[6-[(3R)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;benzoic acid
    2.1.2 InChI
    InChI=1S/C18H21N5O2.C7H6O2/c1-21-17(24)9-16(22-8-4-7-15(20)12-22)23(18(21)25)11-14-6-3-2-5-13(14)10-19;8-7(9)6-4-2-1-3-5-6/h2-3,5-6,9,15H,4,7-8,11-12,20H2,1H3;1-5H,(H,8,9)/t15-;/m1./s1
    2.1.3 InChI Key
    KEJICOXJTRHYAK-XFULWGLBSA-N
    2.1.4 Canonical SMILES
    CN1C(=O)C=C(N(C1=O)CC2=CC=CC=C2C#N)N3CCCC(C3)N.C1=CC=C(C=C1)C(=O)O
    2.1.5 Isomeric SMILES
    CN1C(=O)C=C(N(C1=O)CC2=CC=CC=C2C#N)N3CCC[C@H](C3)N.C1=CC=C(C=C1)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    EEN99869SC
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-((6-((3r)-3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)methyl) Benzonitrile

    2. Alogliptin

    3. Nesina

    4. Syr 322

    5. Syr-322

    6. Syr322

    2.3.2 Depositor-Supplied Synonyms

    1. 850649-62-6

    2. Nesina

    3. Syr 322

    4. Syr-322

    5. Alogliptin (benzoate)

    6. (r)-2-((6-(3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)methyl)benzonitrile Benzoate

    7. 850649-62-6 (benzoate)

    8. Alogliptin (as Benzoate)

    9. Een99869sc

    10. Chebi:72324

    11. 2-((6-((3r)-3-amino-1-piperidinyl)-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)- Pyrimidinyl)methyl)benzonitrile Monobenzoate

    12. 2-[[6-[(3r)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxopyrimidin-1-yl]methyl]benzonitrile;benzoic Acid

    13. 6-((3r)-3-aminopiperidin-1-yl)-1-(2-cyanobenzyl)-3-methylpyrimidin-2,4(1h,3h)-dione Monobenzoate

    14. Benzonitrile, 2-((6-((3r)-3-amino-1-piperidinyl)-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)-pyrimidinyl)methyl)-, Monobenzoate

    15. Alogliptin, Benzoate

    16. Alogliptin Benzoate [usan]

    17. Unii-een99869sc

    18. Mfcd09833195

    19. Alogliptin Benzoate [usan:jan]

    20. Vipidia (tn)

    21. Nesina (tn)

    22. Alogliptin Monobenzoate

    23. Alogliptin(syr-322)

    24. Schembl476231

    25. Chembl227529

    26. Alogliptin Benzoate [mi]

    27. Alogliptin Benzoate (jan/usan)

    28. Alogliptin Benzoate [jan]

    29. Dtxsid20582095

    30. Alogliptin Benzoate [vandf]

    31. Alogliptin Benzoate [mart.]

    32. Bcp08885

    33. Hy-a0023

    34. Ac-021

    35. Alogliptin Benzoate [who-dd]

    36. Akos015917686

    37. Cs-0761

    38. Alogliptin Benzoate [orange Book]

    39. 2-[[6-[(3r)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)-pyrimidinyl]methyl]benzonitrile Benzoate

    40. As-14073

    41. Oseni Component Alogliptin Benzoate

    42. Kazano Component Alogliptin Benzoate

    43. Alogliptin Pound Syr-322 Pound(c)benzoate

    44. Alogliptin Benzoate Component Of Oseni

    45. Am20090704

    46. Alogliptin Benzoate Component Of Kazano

    47. D06553

    48. Q27888443

    49. Syr 322 Benzoate; Syr-322 Benzoate; Syr322 Benzoate

    50. (3r)-1-[3-(2-cyanobenzyl)-1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl]piperidin-3-aminium Benzoate

    51. 2-((6-((3r)-3-aminopiperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)methyl)benzonitrile Monobenzoate

    52. 2-({6-[(3r)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl}methyl)benzonitrile Benzoate

    53. Benzoic Acid--2-({6-[(3r)-3-aminopiperidin-1-yl]-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl}methyl)benzonitrile (1/1)

    54. Benzonitrile, 2-[[6-[(3r)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2h)-pyrimidinyl]methyl]-, Benzoate (1:1)

    2.4 Create Date
    2007-06-18
    3 Chemical and Physical Properties
    Molecular Weight 461.5 g/mol
    Molecular Formula C25H27N5O4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass461.20630436 g/mol
    Monoisotopic Mass461.20630436 g/mol
    Topological Polar Surface Area131 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity726
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameNesina
    PubMed HealthAlogliptin (By mouth)
    Drug ClassesAntidiabetic
    Drug LabelNESINA tablets contain the active ingredient alogliptin, which is a selective, orally bioavailable inhibitor of the enzymatic activity of dipeptidyl peptidase-4 (DPP-4).Chemically, alogliptin is prepared as a benzoate salt, which is identified as 2-(...
    Active IngredientAlogliptin benzoate
    Dosage FormTablet
    RouteOral
    Strengtheq 12.5mg base; eq 6.25mg base; eq 25mg base
    Market StatusPrescription
    CompanyTakeda Pharms Usa

    2 of 2  
    Drug NameNesina
    PubMed HealthAlogliptin (By mouth)
    Drug ClassesAntidiabetic
    Drug LabelNESINA tablets contain the active ingredient alogliptin, which is a selective, orally bioavailable inhibitor of the enzymatic activity of dipeptidyl peptidase-4 (DPP-4).Chemically, alogliptin is prepared as a benzoate salt, which is identified as 2-(...
    Active IngredientAlogliptin benzoate
    Dosage FormTablet
    RouteOral
    Strengtheq 12.5mg base; eq 6.25mg base; eq 25mg base
    Market StatusPrescription
    CompanyTakeda Pharms Usa

    4.2 Drug Indication

    Vipidia is indicated in adults aged 18 years and older with type 2 diabetes mellitus to improve glycaemic control in combination with other glucose lowering medicinal products including insulin, when these, together with diet and exercise, do not provide adequate glycaemic control (see sections 4. 4, 4. 5 and 5. 1 for available data on different combinations).

    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.)

    Incretins

    Peptides which stimulate INSULIN release from the PANCREATIC BETA CELLS following oral nutrient ingestion, or postprandially. (See all compounds classified as Incretins.)

    5.2 ATC Code

    A10BH04

    API Reference Price

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    02-Jan-2021
    16-Aug-2024
    KGS
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    Average Price (USD/KGS)

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