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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.168.764 Edit this at Wikidata
KEGG
UNII
  • 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) X markN
    Key: HHHKFGXWKKUNCY-UHFFFAOYSA-N X markN
  • CCOC(=O)C(CCc1ccccc1)NC1CCCN2CCCC(N2C1=O)C(O)=O
Properties
C22H31N3O5
Molar mass 417.506 g·mol−1
log P 2.212
Acidity (pKa) 2.285
Basicity (pKb) 11.712
Pharmacology
C09AA08 (WHO)
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).
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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.[citation needed]

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.

References

  1. ↑ Szucs, T. (1991). "Cilazapril. A review". Drugs. 41 (Suppl 1): 18–24. doi:10.2165/00003495-199100411-00005. PMID 1712267. S2CID 261123720.
  2. ↑ Jasek, W, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 978-3-85200-181-4.
  3. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 469. ISBN 9783527607495.
  4. ↑ "Cilazapril". Drugs.com. Retrieved 28 May 2010.