cilazapril   Click here for help

GtoPdb Ligand ID: 6459

Synonyms: Inhibace® | Ro 31-2848006 | Vascace®
Approved drug
cilazapril is an approved drug
Compound class: Synthetic organic
Comment: Cilazapril is a prodrug. It is metabolically converted to the drug cilazaprilat. Cilazapril does not appear to have marketing approval for human use in the US or EU, although national approval agencies may have granted marketing authorisation.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 99.18
Molecular weight 417.23
XLogP 2.15
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCOC(=O)C(NC1CCCN2N(C1=O)C(CCC2)C(=O)O)CCc1ccccc1
Isomeric SMILES CCOC(=O)[C@@H](N[C@H]1CCCN2N(C1=O)[C@@H](CCC2)C(=O)O)CCc1ccccc1
InChI 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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
Withdrawn drug? Yes
Is prodrug? Yes
Active form cilazaprilat
IUPAC Name Click here for help
(1S,9S)-9-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-10-oxo-1,2,3,4,6,7,8,9-octahydropyridazino[1,2-a]diazepine-1-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5675 cilazapril
Synonyms Click here for help
Inhibace® | Ro 31-2848006 | Vascace®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9619030
Reactome Reaction Reactome logo R-HSA-9619024
Other databases
CAS Registry No. 88768-40-5
ChEMBL Ligand CHEMBL515606
DrugBank Ligand DB01340
DrugCentral Ligand 641, 641
GtoPdb PubChem SID 178103074
PubChem CID 56330
Search Google for chemical match using the InChIKey HHHKFGXWKKUNCY-FHWLQOOXSA-N
Search Google for chemicals with the same backbone HHHKFGXWKKUNCY
Search PubMed clinical trials cilazapril
Search PubMed titles cilazapril
Search PubMed titles/abstracts cilazapril
UniChem Compound Search for chemical match using the InChIKey HHHKFGXWKKUNCY-FHWLQOOXSA-N
UniChem Connectivity Search for chemical match using the InChIKey HHHKFGXWKKUNCY-FHWLQOOXSA-N
Wikipedia Cilazapril