Cilazapril

Cilazapril

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
ChEMBL	ChEMBL515606
ChemSpider	50831
DrugBank	DB01340
IUPHAR/BPS	6459
Jmol 3D model	Interactive image
KEGG	D07699
PubChem	56330 40467985 (1R,9S)-(2S)-butylamino isomer
UNII	8Q9454114Q
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) Key: HHHKFGXWKKUNCY-UHFFFAOYSA-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 (WHO)
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).
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Infobox references

Cilazapril is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used for the treatment of hypertension and congestive heart failure.^[1][2] It is branded as Dynorm, Inhibace, Vascace and many other names in various countries. None of these is available in the United States as of May 2010.^[3]

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

References

1. Szucs, T. (1991). "Cilazapril. A review". Drugs. 41 Suppl 1: 18–24. doi:10.2165/00003495-199100411-00005. PMID 1712267.
2. Jasek, W, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 978-3-85200-181-4.
3. Drugs.com: Cilazapril