Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H31N3O5.H2O |
| Molecular Weight | 435.5139 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCCN3CCC[C@H](N3C2=O)C(O)=O
InChI
InChIKey=JQRZBPFGBRIWSN-YOTVLOEGSA-N
InChI=1S/C22H31N3O5.H2O/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26;/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28);1H2/t17-,18-,19-;/m0./s1
| Molecular Formula | C22H31N3O5 |
| Molecular Weight | 417.4986 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| 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
https://www.ncbi.nlm.nih.gov/pubmed/7700063 | https://www.ncbi.nlm.nih.gov/pubmed/1532534
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7700063 | https://www.ncbi.nlm.nih.gov/pubmed/1532534
Cilazapril (Vascace and Dynorm are brand names in a number of European countries) is an angiotensin converting enzyme (ACE; kininase II) inhibitor. It competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Cilazapril is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat. The half-life (30–50 hours) of cilazapril allows for once daily dosing unless the hypertension is severe. Cilazapril is used for the treatment of hypertension, congestive heart failure, post-myocardial infarction, and some other indications. Adverse events were mostly observed within the first 8-16 weeks of treatment, with headache, dizziness, fatigue, nausea, cough and chest pain being the most frequent.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1808 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Vascace Approved UseVascace is used to treat the following: - High blood pressure (hypertension) - Chronic (long-term) heart failure.
It works by making your blood vessels relax and widen. This helps to lower your blood pressure. It also makes it easier for your heart to pump blood around your body if you have chronic heart failure. |
|||
| Primary | Vascace Approved UseVascace is used to treat the following: - High blood pressure (hypertension) - Chronic (long-term) heart failure.
It works by making your blood vessels relax and widen. This helps to lower your blood pressure. It also makes it easier for your heart to pump blood around your body if you have chronic heart failure. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Enzyme immunoassay discrimination of a new angiotensin-converting enzyme (ACE) inhibitor, cilazapril, and its active metabolite. | 1987 Mar |
|
| Anti-ischemic effects of cilazapril in patients with both hypertension and angina pectoris. Preliminary report of a pilot study. | 1991 |
|
| Improvement of diastolic filling in hypertensive patients treated with cilazapril. | 1991 |
|
| Angiotensin-converting enzyme inhibitor cilazapril suppresses expression of basic fibroblast growth factor messenger ribonucleic acid and protein in endothelial and intimal smooth muscle cells in a vascular injury model of spontaneous hypertensive rats. | 1998 May |
|
| The acute effects of cilazapril on pulmonary function tests and arterial blood gas changes in patients with pulmonary hypertension. | 2003 |
|
| [A prospective study on the cough mechanism induced by angiotensin-converting enzyme inhibitors in patients with hypertension]. | 2004 Sep |
|
| Nitrofurantoin-induced fulminant hepatitis mimicking autoimmune hepatitis. | 2006 Oct |
|
| Impact of cilazapril on fibrinolytic system in hypertensive patients. | 2008 Jan |
|
| Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. | 2008 Nov |
Sample Use Guides
Swallow each tablet with a drink of water. It does not matter what time of day you take yablet. However, always take it around the same time. Tablet may be taken before or after a meal.
High blood pressure (hypertension): The usual starting dose for adults is 1 mg per day.
Chronic heart failure: The usual starting dose is 0.5 mg per day.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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admin
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Fri Dec 15 15:20:59 GMT 2023
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| Record UNII |
19KW7PI29F
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Validated (UNII)
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C247
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CILAZAPRILAT IS EP IMPURITY B OF CILAZAPRIL
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IMPURITY -> PARENT |
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![Structure of 1,1-Dimethylethyl (1S,9S)-9-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate](/img/f8868d41-85cb-4cc7-802d-cd0638d7d99c.svg "Structure of 1,1-Dimethylethyl (1S,9S)-9-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate")