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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
Structure of IMIDAFENACIN

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)

HIDE SMILES / InChI
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

Description
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.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Imidafenacin showed little binding to brain muscarinic receptors.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 6.8 nM [IC50]
Antagonist
2849
 7.55 nM [Ki]
Antagonist
2849
 1.42 nM [Ki]
Inhibitor
8504
 0.747 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Uritos

Approved Use

For the treatment of Overactive bladder

Launch Date

2007
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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
REVIEW
https://pubmed.ncbi.nlm.nih.gov/23372610/
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

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/23372610/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
Other AEs: Dry mouth...
Other AEs:
Dry mouth
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
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:
https://pubmed.ncbi.nlm.nih.gov/23390360/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23390360/
Disc. AE: Dry mouth...
AEs leading to
discontinuation/dose reduction:
Dry mouth (8.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23390360/
0.5 mg single, oral
Highest studied dose
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
Other AEs: Tachyarrhythmia, Dry mouth...
Other AEs:
Tachyarrhythmia
Dry mouth
Leucocyturia
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/23372610/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
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:
https://pubmed.ncbi.nlm.nih.gov/23390360/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/23390360/
Dry mouth
0.5 mg single, oral
Highest studied dose
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
Leucocyturia
0.5 mg single, oral
Highest studied dose
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
Tachyarrhythmia
0.5 mg single, oral
Highest studied dose
Dose: 0.5 mg
Route: oral
Route: single
Dose: 0.5 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/23372610/
https://pubmed.ncbi.nlm.nih.gov/23390360/
PubMed

PubMed

TitleDatePubMed
Application of a novel combination of near-infrared spectroscopy and a humidity-controlled 96-well plate to the characterization of the polymorphism of imidafenacin.
2010-11
Noninvasive evaluation of brain muscarinic receptor occupancy of oxybutynin, darifenacin and imidafenacin in rats by positron emission tomography.
2010-07-31
The add-on effect of solifenacin for patients with remaining overactive bladder after treatment with tamsulosin for lower urinary tract symptoms suggestive of benign prostatic obstruction.
2010
A randomized, double-blind, placebo- and propiverine-controlled trial of the novel antimuscarinic agent imidafenacin in Japanese patients with overactive bladder.
2009-05
Comparison of the effect of anti-muscarinic agents on bladder activity, urinary ATP level, and autonomic nervous system in rats.
2009-04
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
Long-term safety, tolerability, and efficacy of the novel anti-muscarinic agent imidafenacin in Japanese patients with overactive bladder.
2008-10
A randomized, double-blind, placebo-controlled phase II dose-finding study of the novel anti-muscarinic agent imidafenacin in Japanese patients with overactive bladder.
2008-09
Validation and application of a 96-well format solid-phase extraction and liquid chromatography-tandem mass spectrometry method for the quantitation of digoxin in human plasma.
2008-06-15
[Pharmacological and clinical profile of imidafenacin developed as a new therapeutic agent for overactive bladder].
2008-05
Effect of itraconazole on the pharmacokinetics of imidafenacin in healthy subjects.
2008-03
Absolute bioavailability of imidafenacin after oral administration to healthy subjects.
2008-02
Population pharmacokinetic analysis of a novel muscarinic receptor antagonist, imidafenacin, in healthy volunteers and overactive bladder patients.
2008
No effect of imidafenacin, a novel antimuscarinic drug, on digoxin pharmacokinetics in healthy subjects.
2008
Absorption, metabolism, and excretion of [14C]imidafenacin, a new compound for treatment of overactive bladder, after oral administration to healthy male subjects.
2007-09
Development and validation of bioanalytical methods for imidafenacin (KRP-197/ONO-8025) and its metabolites in human urine by using liquid chromatography-tandem mass spectrometry.
2007-09
Synthesis of the metabolites of 4-(2-methyl-1H-imidazol-1-yl)-2,2-diphenylbutanamide (KRP-197/ONO-8025).
2007-07
Development and validation of bioanalytical methods for Imidafenacin (KRP-197/ONO-8025) and its metabolites in human plasma by liquid chromatography-tandem mass spectrometry.
2007-06-15
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.
2007-02
Pharmacological effects of imidafenacin (KRP-197/ONO-8025), a new bladder selective anti-cholinergic agent, in rats. Comparison of effects on urinary bladder capacity and contraction, salivary secretion and performance in the Morris water maze task.
2007
Effects of imidafenacin (KRP-197/ONO-8025), a new anti-cholinergic agent, on muscarinic acetylcholine receptors. High affinities for M3 and M1 receptor subtypes and selectivity for urinary bladder over salivary gland.
2007
Pharmacological effects of KRP-197 on the human isolated urinary bladder.
2003
Biomimetic oxidation of 2-methylimidazole derivative with a chemical model system for cytochrome P-450.
2002-08
Synthesis and antimuscarinic activity of a series of 4-(1-Imidazolyl)-2,2-diphenylbutyramides: discovery of potent and subtype-selective antimuscarinic agents.
1999-06
Patents

Patents

07868183
1
JP2003201281A
1
JP2010013485A
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
10(–8) to 10(–7) M Imidafenacin (KRP-197) significantly decreased electrical field stimulation-induced acetylcholine release and the contractile responses in a concentration-dependent manner.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:41:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:41:17 GMT 2025
Record UNII
XJR8Y07LJO
Record Status Validated (UNII)
Record Version
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Name Type Language
STAYBLA
Preferred Name English
IMIDAFENACIN
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
URITOS
Brand Name English
IMIDAFENACIN [JAN]
Common Name English
KRP-197
Code English
IMIDAFENACIN [MART.]
Common Name English
ONO-8025
Code English
Imidafenacin [WHO-DD]
Common Name English
imidafenacin [INN]
Common Name English
IMIDAFENACIN [MI]
Common Name English
4-(2-METHYL-1H-IMIDAZOL-1-YL)-2,2-DIPHENYLBUTANAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
Code System Code Type Description
DRUG CENTRAL
4902
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
MERCK INDEX
m11873
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
MESH
C120953
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
DRUG BANK
DB09262
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID00870104
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
FDA UNII
XJR8Y07LJO
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
NCI_THESAURUS
C83789
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
PUBCHEM
6433090
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
CAS
170105-16-5
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
WIKIPEDIA
IMIDAFENACIN
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
INN
8402
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
SMS_ID
100000124434
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL53366
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
EVMPD
SUB32180
Created by admin on Mon Mar 31 18:41:17 GMT 2025 , Edited by admin on Mon Mar 31 18:41:17 GMT 2025
PRIMARY
Related Record Type Details
MUSCARINIC ACETYLCHOLINE RECEPTOR M1
TARGET -> INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
Structure of IMIDAFENACIN
EXCRETED UNCHANGED
URINE
MUSCARINIC ACETYLCHOLINE RECEPTOR M3
TARGET -> INHIBITOR
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A4
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of 4-(2-METHYL-4,5-DIOXOIMIDAZOLIDIN-1-YL)-2,2-DIPHENYLBUTANAMIDE
METABOLITE -> PARENT
2h plasma
PLASMA
Structure of 4-((ACETIMIDOYL)AMINO)-2,2-DIPHENYLBUTANAMIDE
METABOLITE -> PARENT
2h plasma
PLASMA
Structure of 2-ACETYLAMINO-N-(3-CARBAMOYL-3,3-DIPHENYLPROPYL)ACETAMIDE
METABOLITE -> PARENT
URINE
Structure of 3,3-DIPHENYL-2-PYRROLIDINONE
METABOLITE -> PARENT
Structure of N1-(4-AMINO-4-OXO-3,3-DIPHENYLBUTYL)ETHANEDIAMIDE
METABOLITE -> PARENT
URINE
Structure of 4-(2-METHYLIMIDAZOL-1-YL)-2,2-DIPHENYL-BUTANAMIDE N-OXIDE
METABOLITE -> PARENT
URINE
Structure of N-(3-CARBAMOYL-3-(4-HYDROXYPHENYL)-3-PHENYLPROPYL)OXAMIDE
METABOLITE -> PARENT
Structure of 2-((4-AMINO-4-OXO-3,3-DIPHENYLBUTYL)AMINO)-2-OXOACETIC ACID
METABOLITE -> PARENT
URINE
Structure of (2S,3S,4S,5R,6R)-6-(3-(4-AMINO-4-OXO-3,3-DIPHENYL-BUTYL)-2-METHYL-IMIDAZOL-1-YL)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
2h plasma
PLASMA
Related Record Type Details
Structure of IMIDAFENACIN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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