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    Chemistry

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    Also known as: 654671-78-0, Sitagliptin (phosphate), Mk-0431, Chembl393336, 494p4635i6, Mk0431
    Molecular Formula
    C16H18F6N5O5P
    Molecular Weight
    505.31  g/mol
    InChI Key
    IQFYVLUXQXSJJN-SBSPUUFOSA-N
    FDA UNII
    494P4635I6
    Sitagliptin Phosphate
    A pyrazine-derived DIPEPTIDYL-PEPTIDASE IV INHIBITOR and HYPOGLYCEMIC AGENT that increases the levels of the INCRETIN hormones GLUCAGON-LIKE PEPTIDE-1 (GLP-1) and glucose-dependent insulinotropic polypeptide (GIP). It is used in the treatment of TYPE 2 DIABETES.
    1 2D Structure

    Sitagliptin Phosphate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3R)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one;phosphoric acid
    2.1.2 InChI
    InChI=1S/C16H15F6N5O.H3O4P/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22;1-5(2,3)4/h4,6,9H,1-3,5,7,23H2;(H3,1,2,3,4)/t9-;/m1./s1
    2.1.3 InChI Key
    IQFYVLUXQXSJJN-SBSPUUFOSA-N
    2.1.4 Canonical SMILES
    C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(CC3=CC(=C(C=C3F)F)F)N.OP(=O)(O)O
    2.1.5 Isomeric SMILES
    C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C[C@@H](CC3=CC(=C(C=C3F)F)F)N.OP(=O)(O)O
    2.2 Other Identifiers
    2.2.1 UNII
    494P4635I6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 0431, Mk

    2. 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8h)-yl)-1-(2,4,5-trifluorophenyl)butan-2-amine

    3. Anhydrous, Sitagliptin Phosphate

    4. Januvia

    5. Mk 0431

    6. Mk-0431

    7. Mk0431

    8. Monohydrate, Sitagliptin Monophosphate

    9. Monohydrate, Sitagliptin Phosphate

    10. Monophosphate Monohydrate, Sitagliptin

    11. Phosphate Anhydrous, Sitagliptin

    12. Phosphate Monohydrate, Sitagliptin

    13. Phosphate, Sitagliptin

    14. Sitagliptin

    15. Sitagliptin Monophosphate Monohydrate

    16. Sitagliptin Phosphate Anhydrous

    17. Sitagliptin Phosphate Monohydrate

    2.3.2 Depositor-Supplied Synonyms

    1. 654671-78-0

    2. Sitagliptin (phosphate)

    3. Mk-0431

    4. Chembl393336

    5. 494p4635i6

    6. Mk0431

    7. (2r)-4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8h)-yl)-1-(2,4,5-trifluorophenyl)butan-2-amine Phosphate Salt

    8. (3r)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)butan-1-one;phosphoric Acid

    9. (r)-3-amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl)-4-(2,4,5-trifluorophenyl)butan-1-one Phosphate

    10. 1-butanone, 3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8h)-yl]-4-(2,4,5-trifluorophenyl)-, (3r)-, Phosphate (1:1)

    11. Sitagliptin Monophosphate

    12. Sitagliptin Phosphate Anhydrous

    13. (3r)-3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)-1-butanone; Phosphoric Acid

    14. Mk 0431

    15. Sr-05000001748

    16. Unii-494p4635i6

    17. (2r)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8h)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine Phosphate Salt

    18. Mk 431

    19. Mk-0431 Phosphate

    20. Schembl877069

    21. Dtxsid10215789

    22. Hy-13749a

    23. Mfcd09952339

    24. Akos015896098

    25. Sitagliptin Phosphate [who-dd]

    26. Ks-1214

    27. 4-oxo-4-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8h)-yl)-1-(2,4,5-trifluorophenyl)butan-2-amine Phosphate

    28. Sitagliptin Monophosphate Anhydrous [mi]

    29. 671s780

    30. A835125

    31. Sr-05000001748-2

    32. Q27259224

    33. Sitagliptin Phosphate Anhydrous Component Of Janumet

    34. (3r)-3-amino-1-[5,6-dihydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazin-7(8h)-yl]-4-(2,4,5-trifluorophenyl)-1-butanone Phosphate

    35. (3r)-3-azanyl-1-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-[2,4,5-tris(fluoranyl)phenyl]butan-1-one; Phosphoric Acid

    36. 1,2,4-triazolo(4,3-a)pyrazine, 7-((3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl)-5,6,7,8-tetrahydro-3-(trifluoromethyl)-, Phosphate (1:1)

    37. 1269630-53-6

    38. 7-((3r)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl)-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,2,4-triazolo(4,3-a)pyrazinemonophosphate

    39. 7-(3r)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl-5,6,7,8-tetrahydro-3-(trifluoromethyl)-1,2,4-triazolo[4,3-a]pyrazine Phosphate

    2.4 Create Date
    2006-04-29
    3 Chemical and Physical Properties
    Molecular Weight 505.31 g/mol
    Molecular Formula C16H18F6N5O5P
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count4
    Exact Mass505.09497466 g/mol
    Monoisotopic Mass505.09497466 g/mol
    Topological Polar Surface Area155 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity616
    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 4  
    Drug NameJanuvia
    PubMed HealthSitagliptin (By mouth)
    Drug ClassesAntidiabetic
    Drug LabelJANUVIA Tablets contain sitagliptin phosphate, an orally-active inhibitor of the dipeptidyl peptidase-4 (DPP-4) enzyme. Sitagliptin phosphate monohydrate is described chemically as 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahy...
    Active IngredientSitagliptin phosphate
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 50mg base; eq 25mg base
    Market StatusPrescription
    CompanyMerck Sharp Dohme

    2 of 4  
    Drug NameSitagliptin phosphate
    Active IngredientSitagliptin phosphate
    Dosage FormTablet
    Routeoral; Oral
    Strengtheq 100mg base; 25mg; eq 50mg base; 100mg; 50mg; eq 25mg base
    Market StatusTentative Approval
    CompanyMylan Pharms; Apotex; Sandoz; Sun Pharma Global; Watson Labs

    3 of 4  
    Drug NameJanuvia
    PubMed HealthSitagliptin (By mouth)
    Drug ClassesAntidiabetic
    Drug LabelJANUVIA Tablets contain sitagliptin phosphate, an orally-active inhibitor of the dipeptidyl peptidase-4 (DPP-4) enzyme. Sitagliptin phosphate monohydrate is described chemically as 7-[(3R)-3-amino-1-oxo-4-(2,4,5-trifluorophenyl)butyl]-5,6,7,8-tetrahy...
    Active IngredientSitagliptin phosphate
    Dosage FormTablet
    RouteOral
    Strengtheq 100mg base; eq 50mg base; eq 25mg base
    Market StatusPrescription
    CompanyMerck Sharp Dohme

    4 of 4  
    Drug NameSitagliptin phosphate
    Active IngredientSitagliptin phosphate
    Dosage FormTablet
    Routeoral; Oral
    Strengtheq 100mg base; 25mg; eq 50mg base; 100mg; 50mg; eq 25mg base
    Market StatusTentative Approval
    CompanyMylan Pharms; Apotex; Sandoz; Sun Pharma Global; Watson Labs

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    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.)

    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.)

    API Reference Price

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    04-Jan-2021
    29-Nov-2024
    KGS
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