Cilazapril

Cilazapril

Kekulé, stereo, skeletal formula of cilazapril ((1S,9S)-9-[(2S)-2-yl]amin,-1-carbox)
Names
IUPAC name (4S,7S)-7-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-6-oxo-1,2,3,4,7,8,9,10-octahydropyridazino[1,2-a]diazepine-4-carboxylic acid
Identifiers
CAS Number	88768-40-5 N
ChEMBL	ChEMBL515606 N
ChemSpider	50831 N
DrugBank	DB01340 Y
IUPHAR/BPS	6459
Jmol 3D model	Interactive image
KEGG	D07699 Y
PubChem	56330 40467985 (1R,9S)-(2S)-butylamino isomer
UNII	8Q9454114Q N
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	417.51 g·mol−1
log P	2.212
Acidity (pKa)	2.285
Basicity (pKb)	11.712
Pharmacology
ATC code	C09AA08
Legal status	UK: POM (Prescription only)
Routes of administration	Oral
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Cilazapril is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used for the treatment of hypertension and congestive heart failure. It is branded as Inhibace in Canada and other countries, Vascace and Dynorm in a number of European countries, among many other names. None of these is available in the United States as of May 2010.

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

Synthesis

File:Cilazapril synthesis.png

Cilazapril synthesis

See also

• Cilazapril monograph. Lexi-Comp Online, Lexi-Drugs Online, Lexi-Comp Inc. Hudson, OH. Available at: [1]. Accessed October 5, 2008.