Cilazapril

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Cilazapril
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) ☒N
    Key: HHHKFGXWKKUNCY-UHFFFAOYSA-N ☒N
  • 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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Infobox references

Cilazapril is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used for the treatment of hypertension and congestive heart failure.[1][2]

It was patented in 1982 and approved for medical use in 1990.[3]

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.[4]

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. ^ 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.