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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H31N3O5
Molecular Weight 417.4986
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CILAZAPRIL ANHYDROUS

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCCN3CCC[C@H](N3C2=O)C(O)=O

InChI

InChIKey=HHHKFGXWKKUNCY-FHWLQOOXSA-N
InChI=1S/C22H31N3O5/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)/t17-,18-,19-/m0/s1

HIDE SMILES / InChI

Description

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Vascace
Primary
Vascace
PubMed

PubMed

TitleDatePubMed
Enzyme immunoassay discrimination of a new angiotensin-converting enzyme (ACE) inhibitor, cilazapril, and its active metabolite.
1987 Mar
A review of the preclinical cardiovascular pharmacology of cilazapril, a new angiotensin converting enzyme inhibitor.
1989
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
Effects of angiotensin converting enzyme inhibitors and calcium antagonists on atrial natriuretic peptide release and action and on albumin excretion rate in hypertensive insulin-dependent diabetic patients.
1992 Nov
[Follow-up of patients with chronic aortic valve insufficiency with ACE inhibitor therapy].
1997 Dec
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
Effects of cilazapril on endothelial function and pulmonary hypertension in patients with congestive heart failure.
2002 Nov
The acute effects of cilazapril on pulmonary function tests and arterial blood gas changes in patients with pulmonary hypertension.
2003
Impact of cilazapril on fibrinolytic system in hypertensive patients.
2008 Jan
Patents

Sample Use Guides

In Vivo Use Guide
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
Name Type Language
CILAZAPRIL ANHYDROUS
Common Name English
CILAZAPRIL [INN]
Common Name English
CILAZAPRIL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CILAZAPRIL [MI]
Common Name English
CILAZAPRIL [VANDF]
Common Name English
CILAZAPRIL [WHO-DD]
Common Name English
RO-312848006
Code English
(1S,9S)-9-(((S)-1-CARBOXY-3-PHENYLPROPYL)AMINO)OCTAHYDRO-10-OXO-6H-PYRIDAZINO(1,2-A)(1,2)DIAZEPINE-1-CARBOXYLIC ACID 9-ETHYL ESTER
Common Name English
RO-31-2848/006
Code English
ANHYDROUS CILAZAPRIL
Common Name English
6H-PYRIDAZINO(1,2-A)(1,2)DIAZEPINE-1-CARBOXYLIC ACID, 9-((1-(ETHOXYCARBONYL)-3-PHENYLPROPYL)AMINO)OCTAHYDRO-10-OXO-, MONOHYDRATE, (1S-(1.ALPHA.,9.ALPHA.(R*)))
Common Name English
Classification Tree Code System Code
WHO-ATC C09BA08
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
WHO-VATC QC09AA08
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
WHO-ATC C09AA08
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
WHO-VATC QC09BA08
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
NCI_THESAURUS C247
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
Code System Code Type Description
PUBCHEM
56330
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
RXCUI
21102
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY RxNorm
MESH
D017315
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
ChEMBL
CHEMBL515606
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
NCI_THESAURUS
C76134
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
INN
5675
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
WIKIPEDIA
CILAZAPRIL
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
IUPHAR
6459
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
EPA CompTox
88768-40-5
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
MERCK INDEX
M3545
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY Merck Index
CAS
88768-40-5
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
EVMPD
SUB23211
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY
EVMPD
SUB06265MIG
Created by admin on Tue Oct 22 00:20:49 UTC 2019 , Edited by admin on Tue Oct 22 00:20:49 UTC 2019
PRIMARY