Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H27N3O5 |
| Molecular Weight | 389.4455 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCCN3CCC[C@H](N3C2=O)C(O)=O
InChI
InChIKey=UVAUYSRYXACKSC-ULQDDVLXSA-N
InChI=1S/C20H27N3O5/c24-18-15(8-4-12-22-13-5-9-17(20(27)28)23(18)22)21-16(19(25)26)11-10-14-6-2-1-3-7-14/h1-3,6-7,15-17,21H,4-5,8-13H2,(H,25,26)(H,27,28)/t15-,16-,17-/m0/s1
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 |
|---|---|---|
| Cardiovascular effects of the new angiotensin-converting-enzyme inhibitor, cilazapril, in anesthetized and conscious dogs. | 1986 Jan-Feb |
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| Enzyme immunoassay discrimination of a new angiotensin-converting enzyme (ACE) inhibitor, cilazapril, and its active metabolite. | 1987 Mar |
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| A review of the preclinical cardiovascular pharmacology of cilazapril, a new angiotensin converting enzyme inhibitor. | 1989 |
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| Pharmacokinetic and pharmacodynamic interactions between the ACE inhibitor cilazapril and beta-adrenoceptor antagonist propranolol in healthy subjects and in hypertensive patients. | 1989 |
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| Improvement of diastolic filling in hypertensive patients treated with cilazapril. | 1991 |
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| Kinin and angiotensin II receptor antagonists in rats with chronic renal failure: chronic effects on cardio- and renoprotection of angiotensin converting enzyme inhibitors. | 1995 Dec |
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| Improvement of left ventricular diastolic dysfunction in hypertensive patients 1 month after ACE inhibition therapy: evaluation by ultrasonic automated boundary detection. | 1996 |
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| Angiotensin-converting enzyme inhibitor-induced angioedema: late onset, irregular course, and potential role of triggers. | 1997 Apr |
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| [Follow-up of patients with chronic aortic valve insufficiency with ACE inhibitor therapy]. | 1997 Dec |
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| 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 |
|
| Doctor, there's a fly in my soup! Angiotensin-converting enzyme inhibitors, endogenous opioids and visual hallucinations. | 2001 Dec |
|
| [Effect of cilazapril on insulin sensitivity in patients with essential arterial hypertension]. | 2001 May-Jun |
|
| [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 |
|
| Combination of an ACE inhibitor and indapamide improves blood pressure control, but attenuates the beneficial effects of ACE inhibition on plasma adiponectin in patients with essential hypertension. | 2009 Dec |
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
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C247
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C045980
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100000081312
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DTXSID00238043
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DB15565
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WBL76FH528
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5811
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m3545
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C75927
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90139-06-3
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6461
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SUB06266MIG
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CHEMBL2104578
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ACTIVE MOIETY
