U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H27N3O6.ClH
Molecular Weight 441.906
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMIDAPRIL HYDROCHLORIDE

SMILES

Cl.CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@@H](CN(C)C2=O)C(O)=O

InChI

InChIKey=LSLQGMMMRMDXHN-GEUPQXMHSA-N
InChI=1S/C20H27N3O6.ClH/c1-4-29-19(27)15(11-10-14-8-6-5-7-9-14)21-13(2)17(24)23-16(18(25)26)12-22(3)20(23)28;/h5-9,13,15-16,21H,4,10-12H2,1-3H3,(H,25,26);1H/t13-,15-,16-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C20H27N3O6
Molecular Weight 405.4449
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
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 https://www.medicines.org.uk/emc/medicine/31738 http://patient.info/medicine/imidapril-for-high-blood-pressure-tanatril https://www.ncbi.nlm.nih.gov/pubmed/17547476

Imidapril (Tanatril), through its active metabolite imidaprilat, acts as an ACE inhibitor to suppress the conversion of angiotensin I to angiotensin II and thereby reduce total peripheral resistance and systemic blood pressure (BP). In clinical trials, oral imidapril was an effective antihypertensive agent in the treatment of mild to moderate essential hypertension. Some evidence suggests that imidapril also improves exercise capacity in patients with chronic heart failure (CHF) and reduces urinary albumin excretion rate in patients with type 1 diabetes mellitus. Imidapril was well tolerated, with a lower incidence of dry cough than enalapril or benazepril, and is a first choice ACE inhibitor for the treatment of mild to moderate essential hypertension.

CNS Activity

Curator's Comment: non-brain-penetrating ACE inhibitor

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Tanatril

Approved Use

Tanatril is indicated for the treatment of essential hypertension in adults

Launch Date

2007
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
28.9 ng/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
27.1 ng/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.8 ng/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
20.3 ng/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
21.6 ng/mL
5 mg 1 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
18.6 ng/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.2 ng/mL
5 mg 1 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
18.1 ng/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
31.5 ng/mL
10 mg 1 times / hour multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
31.8 ng/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
23.7 ng/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
47.8 ng/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
36.1 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
18.6 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
34.3 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
12 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
113.3 ng × h/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
113.6 ng × h/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
107.8 ng × h/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
246.6 ng × h/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
112 ng × h/mL
5 mg 1 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
107.2 ng × h/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
103.9 ng × h/mL
5 mg 1 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
337.4 ng × h/mL
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
183.3 ng × h/mL
10 mg 1 times / hour multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
188.7 ng × h/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
361 ng × h/mL
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
818.7 ng × h/mL
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
168.4 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
197.1 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
124.3 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
137 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.7 h
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.6 h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
14.8 h
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.6 h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.8 h
5 mg 1 times / day multiple, oral
dose: 5 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.4 h
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
17.7 h
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.5 h
10 mg 1 times / hour multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.5 h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
20.6 h
10 mg 1 times / day multiple, oral
dose: 10 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.4 h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.94 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.83 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.78 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
6.85 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
IMIDAPRILAT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
15%
IMIDAPRIL plasma
Homo sapiens
49%
IMIDAPRILAT plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
40 mg 1 times / day multiple, oral
Higher than recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Nervousness, Palpitations...
Other AEs: Vomiting...
AEs leading to
discontinuation/dose reduction:
Nervousness (3.1%)
Palpitations (3.1%)
Other AEs:
Vomiting (3.1%)
Sources:
5 mg 1 times / day multiple, oral
Recommended
Dose: 5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
AEs

AEs

AESignificanceDosePopulation
Vomiting 3.1%
40 mg 1 times / day multiple, oral
Higher than recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Nervousness 3.1%
Disc. AE
40 mg 1 times / day multiple, oral
Higher than recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Palpitations 3.1%
Disc. AE
40 mg 1 times / day multiple, oral
Higher than recommended
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Imidapril: a review of its use in essential hypertension, Type 1 diabetic nephropathy and chronic heart failure.
2007
Imidapril in heart failure.
2006-09
[Studies on angiotensin I converting enzyme (ACE) inhibitory effect of imidapril. (I). Inhibition of various tissue ACEs in vitro].
1992-07
Patents

Sample Use Guides

Adult: PO Initial: 5 mg once daily at bedtime. Maintenance: 10 mg/day. Max: 20 mg/day. Should be taken on an empty stomach. Take 15 min before meals. However, when initiating therapy, 1st dose should be given at bedtime.
Route of Administration: Oral
In Vitro Use Guide
Imidapril inhibited activity on Angiotensin I converting enzyme (ACE) obtained from pig renal cortex with IC50 9.9uM
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:17:15 GMT 2025
Edited
by admin
on Mon Mar 31 18:17:15 GMT 2025
Record UNII
7NSF9GG1NU
Record Status Validated (UNII)
Record Version
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Name Type Language
IMIDAPRIL MONOHYDROCHLORIDE
MI  
Preferred Name English
IMIDAPRIL HYDROCHLORIDE
JAN   MART.   WHO-DD  
Common Name English
4-IMIDAZOLIDINECARBOXYLIC ACID, 3-((2S)-2-(((1S)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1-METHYL-2-OXO-, MONOHYDROCHLORIDE, (4S)-
Common Name English
IMIDAPRIL HYDROCHLORIDE [JAN]
Common Name English
IMIDAPRIL HYDROCHLORIDE [MART.]
Common Name English
IMIDAPRIL MONOHYDROCHLORIDE [MI]
Common Name English
TA 6366
Code English
TA-6366
Code English
4-IMIDAZOLIDINECARBOXYLIC ACID, 3-((2S)-2-(((1S)-1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1-METHYL-2-OXO-, HYDROCHLORIDE (1:1), (4S)-
Common Name English
3-((2S)-2-((1S)-N-(1-ETHOXYCARBONYL-3-PHENYLPROPYL)AMINO)-PROPIONYL)-1-METHYL-2-OXOIMIDAZOLIDINE-4-CARBOXYLIC ACID, HYDROCHLORIDE-, 4S-
Common Name English
4-IMIDAZOLIDINECARBOXYLIC ACID, 3-(2-((1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)-1-OXOPROPYL)-1-METHYL-2-OXO-, MONOHYDROCHLORIDE, (4S-(3(R*(R*)),4R*))-
Common Name English
IMIDAPRIL HCL
Common Name English
Imidapril hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C247
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
Code System Code Type Description
FDA UNII
7NSF9GG1NU
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID7046912
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
EVMPD
SUB02642MIG
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
RXCUI
259335
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C99550
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL317094
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
MERCK INDEX
m6222
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY Merck Index
CAS
89396-94-1
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
DRUG BANK
DBSALT002072
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
SMS_ID
100000092320
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
PUBCHEM
5485193
Created by admin on Mon Mar 31 18:17:15 GMT 2025 , Edited by admin on Mon Mar 31 18:17:15 GMT 2025
PRIMARY
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