U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

Description
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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.
Primary
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

PubMed

TitleDatePubMed
Cardiovascular effects of the new angiotensin-converting-enzyme inhibitor, cilazapril, in anesthetized and conscious dogs.
1986 Jan-Feb
Pharmacokinetic and pharmacodynamic interactions between the ACE inhibitor cilazapril and beta-adrenoceptor antagonist propranolol in healthy subjects and in hypertensive patients.
1989
Anti-ischemic effects of cilazapril in patients with both hypertension and angina pectoris. Preliminary report of a pilot study.
1991
Doctor, there's a fly in my soup! Angiotensin-converting enzyme inhibitors, endogenous opioids and visual hallucinations.
2001 Dec
Effects of cilazapril on endothelial function and pulmonary hypertension in patients with congestive heart failure.
2002 Nov
Patents

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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:02:02 UTC 2023
Edited
by admin
on Sat Dec 16 17:02:02 UTC 2023
Record UNII
8Q9454114Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CILAZAPRIL ANHYDROUS
Common Name English
cilazapril [INN]
Common 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 Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
WHO-VATC QC09AA08
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
WHO-ATC C09AA08
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
WHO-VATC QC09BA08
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
NCI_THESAURUS C247
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
Code System Code Type Description
PUBCHEM
56330
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
RXCUI
21102
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY RxNorm
MESH
D017315
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL515606
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
NCI_THESAURUS
C76134
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
DRUG CENTRAL
641
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
INN
5675
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
WIKIPEDIA
CILAZAPRIL
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
DRUG BANK
DB01340
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
FDA UNII
8Q9454114Q
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
IUPHAR
6459
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID1048629
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
MERCK INDEX
m3545
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY Merck Index
CAS
88768-40-5
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
CHEBI
3698
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
EVMPD
SUB23211
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
EVMPD
SUB06265MIG
Created by admin on Sat Dec 16 17:02:02 UTC 2023 , Edited by admin on Sat Dec 16 17:02:02 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY