Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H27N3O6 |
| Molecular Weight | 405.4449 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
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=KLZWOWYOHUKJIG-BPUTZDHNSA-N
InChI=1S/C20H27N3O6/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)/t13-,15-,16-/m0/s1
| 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 |
DescriptionSources: https://www.drugs.com/uk/pdf/leaflet/815031.pdfCurator'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
Sources: https://www.drugs.com/uk/pdf/leaflet/815031.pdf
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
Sources: http://www.medscape.org/viewarticle/493130_7
Curator's Comment: non-brain-penetrating ACE inhibitor
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2096989 |
|||
Target ID: CHEMBL1808 |
9.9 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Tanatril Approved UseTanatril is indicated for the treatment of essential hypertension in adults Launch Date2007 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15% |
IMIDAPRIL plasma | Homo sapiens |
||
49% |
IMIDAPRILAT plasma | Homo sapiens |
Doses
| Dose | Population | Adverse 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%) Other AEs:Palpitations (3.1%) 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
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| Title | Date | PubMed |
|---|---|---|
| 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 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2913292
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
Edited
Mon Mar 31 18:25:03 GMT 2025
by
admin
on
Mon Mar 31 18:25:03 GMT 2025
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| Record UNII |
BW7H1TJS22
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| Record Status |
Validated (UNII)
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| Record Version |
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Official Name | English | ||
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Preferred Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
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WHO-ATC |
C09AA16
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NCI_THESAURUS |
C247
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WHO-VATC |
QC09AA16
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100000083936
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60245
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5464343
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BW7H1TJS22
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6394
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IMIDAPRIL
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6377
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CHEMBL317094
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m6222
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C72908
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89371-37-9
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DTXSID2048242
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135654
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C065166
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SUB08143MIG
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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