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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.