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    Danegaptide

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: 943134-39-2, Gap-134, (2s,4r)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid, Danegaptida, Zp1609, Pa0y7735at
    Molecular Formula
    C14H17N3O4
    Molecular Weight
    291.30  g/mol
    InChI Key
    BIZKIHUJGMSVFD-MNOVXSKESA-N
    FDA UNII
    PA0Y7735AT
    an antiarrhythmia agent with cytoprotective activity
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C14H17N3O4/c15-7-12(18)17-8-10(6-11(17)14(20)21)16-13(19)9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,19)(H,20,21)/t10-,11+/m1/s1
    2.1.3 InChI Key
    BIZKIHUJGMSVFD-MNOVXSKESA-N
    2.2 Other Identifiers
    2.2.1 UNII
    PA0Y7735AT
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Zp1609

    2.3.2 Depositor-Supplied Synonyms

    1. 943134-39-2

    2. Gap-134

    3. (2s,4r)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic Acid

    4. Danegaptida

    5. Zp1609

    6. Pa0y7735at

    7. Zp-1609

    8. Glycyl-(4r)-4-(benzoylamino)-l-proline

    9. L-proline, Glycyl-4-(benzoylamino)-, (4r)-

    10. Dtxsid201026039

    11. (2s,4r)-1-(aminoacetyl)-4-(benzoylamino)pyrrolidine-2-carboxylic Acid

    12. Danegaptidum

    13. [2s,4r]-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic Acid

    14. Refchem:919625

    15. Dtxcid301510295

    16. 943134-39-2 (free Base)

    17. (2s,4r)-4-benzamido-1-glycylpyrrolidine-2-carboxylic Acid

    18. Mfcd16619374

    19. Danegaptide [usan]

    20. Danegaptide [usan:inn]

    21. Unii-pa0y7735at

    22. (2s,4r)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylicacid

    23. Danegaptide [inn]

    24. Danegaptide (usan/inn)

    25. Danegaptide [who-dd]

    26. Chembl560592

    27. Schembl2399763

    28. Bizkihujgmsvfd-mnovxskesa-n

    29. Chebi:177853

    30. Akos030527026

    31. Cs-1100

    32. Db11821

    33. Hy-10913

    34. Db-289821

    35. Ns00072457

    36. D09599

    37. D95155

    38. 134a392

    39. Brd-k35589454-003-01-1

    40. Q27286426

    41. (2s,4r) 1-(2-amino-acetyl)-4-benzoylamino-pyrrolidine-2-carboxylic Acid

    42. (2s,4r)-1-(2-azanylethanoyl)-4-benzamido-pyrrolidine-2-carboxylic Acid

    43. (2s4r) 1-(2-amino-acetyl)-4-benzoylamino-pyrrolidine-2-carboxylic Acid

    44. (2s4r)1-(2-amino-acetyl)-4-benzoylamino-pyrrolidine-2-carboxylic Acid

    2.4 Create Date
    2007-08-09
    3 Chemical and Physical Properties
    Molecular Weight 291.30 g/mol
    Molecular Formula C14H17N3O4
    XLogP3-2.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area113
    Heavy Atom Count21
    Formal Charge0
    Complexity420
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Mechanism of Action

    Danegaptide, a small modified dipeptide, is a selective second generation gap junction modifier with oral bioavailability. Danegaptide prevents postoperative atrial fibrillation (AF) and chronic AF in large animal models. In a canine model of acute sterile pericarditis, Danegaptide significantly reduced AF duration and overall AF burden. Danegaptide has a similar mechanism of action to its parent compound rotigaptide. Rotigaptide is a synthetic antiarrhythmic peptide (AAP) analogue which has been tested in vitro which shows prevention of prevents metabolic stress-induced atrial conduction velocity (CV) and rapidly reverts established atrial CV slowing. Rogitapeptide enhances gap junction conductance and coupling, increasing the amount of small molecules such as ions, metabolites and secondary messengers passing from one cell to another.