CILAZAPRIL

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1712267
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
Angiotensin-converting enzyme 97 Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1382157 \| https://www.ncbi.nlm.nih.gov/pubmed/10205231 \| https://www.ncbi.nlm.nih.gov/pubmed/10398211	Inhibitor 8297
Angiotensin-converting enzyme 97 Target ID: CHEMBL1808 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8869081	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.drugs.com/uk/vascace-5-mg-film-coated-tablets-leaflet.html	Primary		Approved 8429	Vascace Approved Use Vascace 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.
Chronic heart failure 21 Sources: https://www.drugs.com/uk/vascace-5-mg-film-coated-tablets-leaflet.html	Primary		Approved 8429	Vascace Approved Use Vascace 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	2419701
Enzyme immunoassay discrimination of a new angiotensin-converting enzyme (ACE) inhibitor, cilazapril, and its active metabolite.	1987 Mar	3035170
A review of the preclinical cardiovascular pharmacology of cilazapril, a new angiotensin converting enzyme inhibitor.	1989	2527528
Short term safety assessment of cilazapril.	1993 Nov 24	8247432
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	8903652
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	9640960
[Effect of cilazapril on insulin sensitivity in patients with essential arterial hypertension].	2001 May-Jun	11797459
The acute effects of cilazapril on pulmonary function tests and arterial blood gas changes in patients with pulmonary hypertension.	2003	15018019
Combined therapy of cilazapril and losartan has no additive effects in ameliorating adriamycin-induced glomerulopathy.	2004	15331931
[A prospective study on the cough mechanism induced by angiotensin-converting enzyme inhibitors in patients with hypertension].	2004 Sep	15498266
Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited.	2008 Nov	18713951

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

In Vitro Use Guide

Unknown

Name

Type

Language

CILAZAPRIL

Official Name

English

CILAZAPRILUM

Common Name

English

INHIBACE

Brand Name

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 monohydrate

Common Name

English

CILAZAPRIL MONOHYDRATE

Common Name

English

CILAZAPRIL [EP MONOGRAPH]

Common Name

English

JUSTOR

Brand Name

English

CILAZAPRIL [USAN]

Common Name

English

RO 31-2848/006

Code

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.A(R*)))-

Common Name

English

Cilazapril monohydrate [WHO-DD]

Common Name

English

CILAZAPRIL MONOHYDRATE [MI]

Common Name

English

CILAZAPRIL HYDRATE [JAN]

Common Name

English

INITISS

Brand Name

English

VASCACE

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C247