Cilazapril

Cilazapril

Kekulé, stereo, skeletal formula of cilazapril ((1S,9S)-9-[(2S)-2-yl]amin,-1-carbox) Kekulé, stereo, skeletal formula of cilazapril ((1S,9S)-9-[(2S)-2-yl]amin,-1-carbox)
Names
Preferred IUPAC name (1S,9S)-9-{[(2S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid
Identifiers
CAS Number	88768-40-5 ☒N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3698
ChEMBL	ChEMBL515606 ☒N
ChemSpider	50831 ☒N
DrugBank	DB01340 checkY
ECHA InfoCard
E number
IUPHAR/BPS	6459
KEGG	D07699 checkY
PubChem CID	56330 40467985 (1R,9S)-(2S)-butylamino isomer
UNII	8Q9454114Q ☒N
CompTox Dashboard (EPA)	{{#property:P3117}}
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) ☒N Key: HHHKFGXWKKUNCY-UHFFFAOYSA-N ☒N
SMILES CCOC(=O)C(CCc1ccccc1)NC1CCCN2CCCC(N2C1=O)C(O)=O
Properties
Chemical formula	C22H31N3O5
Molar mass	417.506 g·mol−1
log P	2.212
Acidity (pKa)	2.285
Basicity (pKb)	11.712
Pharmacology
ATC code	C09AA08 (WHO)
Routes of administration	Oral
Legal status	UK: POM (Prescription only)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is checkY☒N ?) Infobox references

Cilazapril is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used for the treatment of hypertension and congestive heart failure.

It was patented in 1982 and approved for medical use in 1990.

Chemistry

Of the eight possible stereoisomers, only the all-(S)-form is medically viable.

Brand names

It is branded as Dynorm, Inhibace, Vascace and many other names in various countries. None of these are available in the United States as of May 2010.