Cilazapril (CED0008499)

Record Information

Version

1.0

Creation Date

2016-05-22 06:35:51 UTC

Update Date

2026-08-21 22:59:55 UTC

Accession Number

CHEM019869

Identification

Common Name

Cilazapril

Class

Small Molecule

Description

Cilazapril is an organic compound with the formula C22H31N3O5 and an average molecular weight of 417.50 g/mol. Cilazapril belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. It is utilized in healthcare, pharmaceuticals, and veterinary products as an ACE inhibitor, with oral administration serving as the recorded exposure route. The compound acts as an inhibitor of the protein target Angiotensin-converting enzyme (ACE).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cilazapril anhydrous	ChEBI
Cilazaprilum	ChEBI
Dynorm	ChEBI
Inhibace	ChEBI
Ro 34-2848	ChEBI
Vascace	ChEBI
Vascase	ChEBI
Monohydrate, cilazapril	HMDB
Cilazapril monohydrate	HMDB
Cilazapril, (s*)-isomer	HMDB
Hydrate, cilazapril	HMDB
Anhydrous, cilazapril	HMDB
Cilazapril hydrate	HMDB
Cilazapril monohydrobromide	HMDB
Cilazapril, anhydrous	HMDB
Monohydrobromide, cilazapril	HMDB

Chemical Formula

C₂₂H₃₁N₃O₅

Average Molecular Mass

417.499 g/mol

Monoisotopic Mass

417.226 g/mol

CAS Registry Number

88768-40-5

IUPAC Name

(1S,9S)-9-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

Traditional Name

inhibace

SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]1CCCN2CCC[C@H](N2C1=O)C(O)=O

InChI Identifier

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

InChI Key

HHHKFGXWKKUNCY-FHWLQOOXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Alpha-amino acid ester
Alpha-amino acid or derivatives
1,2-diazepane
Fatty acid ester
Diazepane
Aralkylamine
Dicarboxylic acid or derivatives
1,2-diazinane
Pyridazine
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Carboxylic acid hydrazide
Amino acid
Amino acid or derivatives
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.06 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	-0.0079	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.41	ChemAxon
pKa (Strongest Basic)	5.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.18 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.56 m³·mol⁻¹	ChemAxon
Polarizability	44.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-3119000000-cf816839d9e62aaeb51d	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-014i-3100900000-8a98b7cfd4306c863f3b	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0114900000-46b169656e56da84df00	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00r6-3339300000-597e65efc2ccd4259fc6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-7930000000-01cd40a3307d1d9136e1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0100-2609400000-2b63f9aade5f2408e90c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fs-2029000000-ef46b50c866af838f6d5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-9413000000-bf81f08b26484eff95d0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0001900000-2155fa52bd310940aaa1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00kf-0129300000-d64d5ab791860881b405	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0560-5901000000-8c919145e29e13e6d804	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0001900000-13fb2fadf7c261ea1f97	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-3289700000-05092f6b096b7ae757aa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0019-2982000000-4f5dadbd2ce238e96eef	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2224.0	Log mg/kg	[1300:4000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
295	ACE inhibitors	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

4 pathways

Cilazapril Action Pathway

Cilazapril Metabolism Pathway

Cilazapril ACE inhibitor Action Pathway

Cilazapril Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Angiotensin-converting enzyme	P12821	Humans	Predicted (SEA)	4.67095
Click to view 3D structure	Angiotensin-converting enzyme	P12822	Oryctolagus cuniculus	Predicted (SEA)	3.81461
Click to view 3D structure	Angiotensin-converting enzyme	P47820	Rattus norvegicus	Predicted (SEA)	3.11397
Click to view 3D structure	Prolyl endopeptidase	Q9XTA2	Bos taurus	Predicted (SEA)	4.35956
Click to view 3D structure	Neprilysin	P07861	Rattus norvegicus	Predicted (SEA)	32.6188
Click to view 3D structure	Prolyl endopeptidase	P23687	Sus scrofa	Predicted (SEA)	7.62922
Click to view 3D structure	Angiotensin-converting enzyme 2	Q5EGZ1	Rattus norvegicus	Predicted (SEA)	2.02408
Click to view 3D structure	FK506 binding protein 12	Q8QGU2	Gallus gallus	Predicted (SEA)	2.56902
Click to view 3D structure	Prolyl endopeptidase	P48147	Humans	Predicted (SEA)	13.7793
Click to view 3D structure	Prolyl endopeptidase	P27028	Elizabethkingia meningoseptica	Predicted (SEA)	9.41976
Click to view 3D structure	Prolyl endopeptidase	Q9QUR6	Mus musculus	Predicted (SEA)	6.53933
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	474.958
Click to view 3D structure	Peptidyl-prolyl cis-trans isomerase FKBP1A	Q62658	Rattus norvegicus	Predicted (SEA)	3.11397
Click to view 3D structure	Neprilysin	P08049	Oryctolagus cuniculus	Predicted (SEA)	86.8797
Click to view 3D structure	Cathepsin B	P07858	Humans	Predicted (SEA)	179.832
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	285.707
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	325.176
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	284.072
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	223.817
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	144.566
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	441.327
Click to view 3D structure	Interleukin-2 receptor subunit alpha	P01589	Humans	Predicted (SEA)	11.2881
Click to view 3D structure	Prolyl endopeptidase	O70196	Rattus norvegicus	Predicted (SEA)	6.53933
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	222.804
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	163.873