Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H21N3O |
| Molecular Weight | 319.4002 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=NC=CN1CCC(C(N)=O)(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=SQKXYSGRELMAAU-UHFFFAOYSA-N
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)
| Molecular Formula | C20H21N3O |
| Molecular Weight | 319.4002 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/25636812
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/25636812
Imidafenacin (KRP-197/ONO-8025) is the latest antimuscarinic (AM) developed for the treatment of overactive bladder syndrome (OAB) and, at the moment, it is marketed only in Japan. It has high affinities for the M3 and M1 muscarinic receptor subtypes, a low affinity for M2 receptors, and a potent inhibitory activity against rhythmic bladder contractions. Imidafenacin has excellent efficacy, tolerability, and safety. It is indicated for patients with nocturia, nocturnal polyuria, and benign prostatic hyperplasia.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0006813 |
6.8 nM [IC50] | ||
Target ID: CHEMBL216 |
7.55 nM [Ki] | ||
Target ID: CHEMBL245 |
1.42 nM [Ki] | ||
Target ID: GO:0061526 |
0.747 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Uritos Approved UseFor the treatment of Overactive bladder Launch Date2007 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.86 ng × eq/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17567733/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
416 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18251758/ |
0.1 mg single, oral dose: 0.1 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
476 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18251758/ |
0.028 mg single, intravenous dose: 0.028 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1240 pg/mL |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1240 pg/mL |
0.25 mg 2 times / day multiple, oral dose: 0.25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
109 pg/mL |
0.025 mg single, oral dose: 0.025 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
180 pg/mL |
0.05 mg single, oral dose: 0.05 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
382 pg/mL |
0.1 mg single, oral dose: 0.1 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1010 pg/mL |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1940 pg/mL |
0.5 mg single, oral dose: 0.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
83.06 ng × eq × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17567733/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2060 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18251758/ |
0.1 mg single, oral dose: 0.1 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
993 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18251758/ |
0.028 mg single, intravenous dose: 0.028 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5580 pg × h/mL |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
72.11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17567733/ |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18251758/ |
0.1 mg single, oral dose: 0.1 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18251758/ |
0.028 mg single, intravenous dose: 0.028 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2.8 h |
0.25 mg single, oral dose: 0.25 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.7 h |
0.25 mg 2 times / day multiple, oral dose: 0.25 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
IMIDAFENACIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
0.25 mg 2 times / day multiple, oral Highest studied dose Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Other AEs: Dry mouth... |
0.25 mg 2 times / day multiple, oral Highest studied dose Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Dry mouth... AEs leading to discontinuation/dose reduction: Dry mouth (8.9%) Sources: |
0.5 mg single, oral Highest studied dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
Other AEs: Tachyarrhythmia, Dry mouth... Other AEs: Tachyarrhythmia Sources: Dry mouth Leucocyturia |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Dry mouth | 0.25 mg 2 times / day multiple, oral Highest studied dose Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
|
| Dry mouth | 8.9% Disc. AE |
0.25 mg 2 times / day multiple, oral Highest studied dose Dose: 0.25 mg, 2 times / day Route: oral Route: multiple Dose: 0.25 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Dry mouth | 0.5 mg single, oral Highest studied dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
|
| Leucocyturia | 0.5 mg single, oral Highest studied dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
|
| Tachyarrhythmia | 0.5 mg single, oral Highest studied dose Dose: 0.5 mg Route: oral Route: single Dose: 0.5 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Synthesis and antimuscarinic activity of a series of 4-(1-Imidazolyl)-2,2-diphenylbutyramides: discovery of potent and subtype-selective antimuscarinic agents. | 1999 Jun |
|
| Biomimetic oxidation of 2-methylimidazole derivative with a chemical model system for cytochrome P-450. | 2002 Aug |
|
| Pharmacological effects of KRP-197 on the human isolated urinary bladder. | 2003 |
|
| Drug-drug interactions in the metabolism of imidafenacin: role of the human cytochrome P450 enzymes and UDP-glucuronic acid transferases, and potential of imidafenacin to inhibit human cytochrome P450 enzymes. | 2007 Feb |
|
| Synthesis of the metabolites of 4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide (KRP-197/ONO-8025). | 2007 Jul |
|
| Absorption, metabolism, and excretion of [14C]imidafenacin, a new compound for treatment of overactive bladder, after oral administration to healthy male subjects. | 2007 Sep |
|
| No effect of imidafenacin, a novel antimuscarinic drug, on digoxin pharmacokinetics in healthy subjects. | 2008 |
|
| Absolute bioavailability of imidafenacin after oral administration to healthy subjects. | 2008 Feb |
|
| Effect of itraconazole on the pharmacokinetics of imidafenacin in healthy subjects. | 2008 Mar |
|
| [Pharmacological and clinical profile of imidafenacin developed as a new therapeutic agent for overactive bladder]. | 2008 May |
|
| Long-term safety, tolerability, and efficacy of the novel anti-muscarinic agent imidafenacin in Japanese patients with overactive bladder. | 2008 Oct |
|
| A randomized, double-blind, placebo-controlled phase II dose-finding study of the novel anti-muscarinic agent imidafenacin in Japanese patients with overactive bladder. | 2008 Sep |
|
| Response to "Suspected differential interactions of digoxin with imidafenacin and propantheline; some thoughts for introspection". | 2009 |
|
| Suspected differential interactions of digoxin with imidafenacin and propantheline; some thoughts for introspection. | 2009 |
|
| Application of a novel combination of near-infrared spectroscopy and a humidity-controlled 96-well plate to the characterization of the polymorphism of imidafenacin. | 2010 Nov |
Patents
Sample Use Guides
Usually, for adults, a single dose of 0.1mg as imidafenacin is orally administered, twice daily, after each meal in the morning and evening. If the desired efficacy is not observed a single dose can be increased up to 0.2mg (0.4mg daily).
Route of Administration:
Oral
| Substance Class |
Chemical
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C29704
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| Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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EXCRETED UNCHANGED |
URINE
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
2h plasma
PLASMA
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METABOLITE -> PARENT |
2h plasma
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
2h plasma
PLASMA
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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