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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3698;
ChEMBL	ChEMBL515606 ;
ChemSpider	50831 ;
DrugBank	DB01340 ;
ECHA InfoCard	100.168.764
IUPHAR/BPS	6459;
KEGG	D07699 ;
PubChem CID	56330; 40467985 (1R,9S)-(2S)-butylamino isomer;
UNII	8Q9454114Q ;
CompTox Dashboard (EPA)	DTXSID1048629 ;
	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	417.506 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).

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.

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

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

[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.

[Fis2006-3] 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.

[1]

[2]

[3]

[4]

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
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3698
ChEMBL	ChEMBL515606
ChemSpider	50831
DrugBank	DB01340
ECHA InfoCard	100.168.764
IUPHAR/BPS	6459
KEGG	D07699
PubChem CID	56330 40467985 (1R,9S)-(2S)-butylamino isomer
UNII	8Q9454114Q
CompTox Dashboard (EPA)	DTXSID1048629
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	417.506 g·mol⁻¹
log P	2.212
Acidity (pK_a)	2.285
Basicity (pK_b)	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).