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    Imidafenacin

    ACTIVE PHARMA INGREDIENTS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

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    2D Structure
    Also known as: 170105-16-5, Uritos, Staybla, Krp-197, 4-(2-methyl-1h-imidazol-1-yl)-2,2-diphenylbutanamide, Imidafenacin [inn]
    Molecular Formula
    C20H21N3O
    Molecular Weight
    319.4  g/mol
    InChI Key
    SQKXYSGRELMAAU-UHFFFAOYSA-N
    FDA UNII
    XJR8Y07LJO
    Imidafenacin is an antispasmodic agent with anticholinergic effects. It antagonizes muscarinic receptors in the bladder to reduce the frequency of urination in the treatment of overactive bladder. It is marketed in Japan under the tradenames Staybla by Ono Pharmaceutical and Uritos by Kyojin Pharmaceutical.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-(2-methylimidazol-1-yl)-2,2-diphenylbutanamide
    2.1.2 InChI
    InChI=1S/C20H21N3O/c1-16-22-13-15-23(16)14-12-20(19(21)24,17-8-4-2-5-9-17)18-10-6-3-7-11-18/h2-11,13,15H,12,14H2,1H3,(H2,21,24)
    2.1.3 InChI Key
    SQKXYSGRELMAAU-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=NC=CN1CCC(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    XJR8Y07LJO
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Krp 197

    2. Krp-197

    2.3.2 Depositor-Supplied Synonyms

    1. 170105-16-5

    2. Uritos

    3. Staybla

    4. Krp-197

    5. 4-(2-methyl-1h-imidazol-1-yl)-2,2-diphenylbutanamide

    6. Imidafenacin [inn]

    7. 4-(2-methyl-1-imidazolyl)-2,2-diphenylbutanamide

    8. Ono-8025

    9. Xjr8y07ljo

    10. 4-(2-methylimidazol-1-yl)-2,2-diphenylbutanamide

    11. Krp-197;ono-8025

    12. Krp 197

    13. Ono 8025

    14. Unii-xjr8y07ljo

    15. Staybla (tn)

    16. Uritos (tn)

    17. Imidafenacin (jan/inn)

    18. Imidafenacin [mi]

    19. Imidafenacin [jan]

    20. Imidafenacin [mart.]

    21. Chembl53366

    22. Imidafenacin [who-dd]

    23. Schembl929680

    24. Zinc7368

    25. Dtxsid00870104

    26. Chebi:134720

    27. Hms3886c04

    28. Bcp10054

    29. Ex-a4417

    30. Hy-b0662

    31. Mfcd09833703

    32. S5385

    33. Akos030526649

    34. Am84591

    35. Ccg-267694

    36. Cs-3681

    37. Db09262

    38. Ncgc00183110-01

    39. Ncgc00183110-02

    40. As-47648

    41. Db-119256

    42. Imidafenacin Hydrochloride, >=95% (hplc)

    43. Ft-0670290

    44. D06273

    45. F14841

    46. 105i165

    47. A882053

    48. L001601

    49. J-521484

    50. Q6003989

    51. 1h-imidazole-1-butanamide, 2-methyl-alpha,alpha-diphenyl-

    52. 4-(2-methyl-1-imidazolyl)-2,2-diphenylbutanamide Hydrochloride

    53. 2-methyl-

    54. A,

    55. A-diphenyl-1h-imidazole-1-butanamide Hydrochloride

    56. 4-(2-methyl-1h-imidazol-1-yl)-2,2-diphenylbutanamide, Aldrichcpr

    2.4 Create Date
    2006-04-28
    3 Chemical and Physical Properties
    Molecular Weight 319.4 g/mol
    Molecular Formula C20H21N3O
    XLogP32.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count6
    Exact Mass319.168462302 g/mol
    Monoisotopic Mass319.168462302 g/mol
    Topological Polar Surface Area60.9 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity395
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Used in the treatment of overactive bladder.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Imidafenacin is an antimuscarinic agent which acts to reduce the frequency of urination in patients with overactive bladder.

    5.2 Absorption, Distribution and Excretion

    Absorption

    The absolute oral bioavailability is 57.8%. Tmax is 1-3 h after administration.

    Route of Elimination

    10% is excreted in the urine as the parent compound. Most is eliminated by metabolism thought to be mediated by CYP3A4 and UGT1A4.

    Volume of Distribution

    The estimated volume of distribution is 43.9 L.

    Clearance

    The estimated clearance is 21.2 L/h.

    5.3 Metabolism/Metabolites

    Thought to be metabolized v by CYP3A4 and UGT1A4. No active metabolites have been observed.

    5.4 Biological Half-Life

    The half life of elimination is 3 h.

    5.5 Mechanism of Action

    Imidafenacin binds to and antagonizes muscarinic M1 and M3 receptors with high affinity. It also antagonizes muscarinic M2 receptors but with lower affinity. M3 receptors stimulate contraction of the detrusor muscle in the bladder via release of calcium from the sarcoplasmic reticulum. M2 receptors are also present in the detrusor muscle but serve to inhibit adenylate cyclase which reduces the relaxation mediated by adrenergic receptors. Finally, M1 receptors are present on the parasympathetic neurons which release acetylcholine in the bladder. They act as an autocrine positive feedback loop and further increase release of acetylcholine. Antagonism of these receptors by imidafenacin prevents contraction of the bladder's detrusor muscle, prevents inhibition of the relation produced by sympathetic tone, and reduces acetylcholine release. Together these reduce the frequency of urination.