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Cilazapril

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Antihypertensive drug of the ACE inhibitor class

Cilazapril
Names
Kekulé, stereo, skeletal formula of cilazapril ((1S,9S)-9-[(2S)-2-yl]amin,-1-carbox)
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
CAS Number	88768-40-5^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3698
ChEMBL	ChEMBL515606^N
ChemSpider	50831^N
DrugBank	DB01340^Y
ECHA InfoCard	100.168.764
IUPHAR/BPS	6459
KEGG	D07699^Y
PubChem CID	56330 40467985 (1R,9S)-(2S)-butylamino isomer
UNII	8Q9454114Q^N
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)^N Key: HHHKFGXWKKUNCY-UHFFFAOYSA-N^N
SMILES CCOC(=O)C(CCc1ccccc1)NC1CCCN2CCCC(N2C1=O)C(O)=O
Properties
Chemical formula	C₂₂H₃₁N₃O₅
Molar mass	417.506 g·mol⁻¹
logP	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 theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Cilazapril is anangiotensin-converting enzyme inhibitor (ACE inhibitor) used for the treatment ofhypertension andcongestive heart failure.^[1]^[2]

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

Chemistry

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Of the eight possiblestereoisomers, only the all-(S)-form is medically viable.^{[citation needed]}

Brand names

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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

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^Szucs, T. (1991). "Cilazapril. A review".Drugs.41 (Suppl 1):18–24.doi:10.2165/00003495-199100411-00005.PMID 1712267.S2CID 261123720.
^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.

v t e Antihypertensive drugs acting on therenin–angiotensin system (C09)
ACE inhibitors ("-pril")	Sulfhydryl-containing:Captopril Rentiapril Zofenopril (+nebivolol) Dicarboxylate-containing:Enalapril^# (+lercanidipine,+nitrendipine) Benazepril (+amlodipine,+pimobendan) Cilazapril Delapril (+manidipine) Imidapril Lisinopril (+amlodipine,+HCT) Moexipril Perindopril (+amlodipine,+bisoprolol,+indapamide,+amlodipine and indapamide,+bisoprolol and amlodipine,+bisoprolol, amlodipine, and indapamide) Quinapril (+HCT) Ramipril (+amlodipine,+amlodipine and HCT,+bisoprolol,+felodipine) Spirapril Temocapril Trandolapril (+verapamil) Phosphonate-containing:Ceronapril Fosinopril (+HCT) Other/ungrouped:Alacepril
AIIRAs ("-sartan")	Azilsartan Candesartan (+amlodipine,+amlodipine and HCT) Eprosartan Fimasartan Irbesartan (+amlodipine,+amlodipine and HCT,+HCT) Losartan (+amlodipine,+HCT) Olmesartan (+amlodipine,+amlodipine and HCT,+HCT) Tasosartan^§ Telmisartan (+amlodipine,+amlodipine and HCT,+amlodipine and indapamide,+HCT) Valsartan (+aliskiren,+amlodipine,+amlodipine and HCT,+HCT,+lercanidipine,+nebivolol,+sacubitril)
Renin inhibitors ("-kiren")	Aliskiren (+amlodipine,+HCT,+amlodipine and HCT) Remikiren^§
DualACE/NEP inhibitors	Gemopatrilat Ilepatril Omapatrilat Sampatrilat
Neprilysin inhibitors	Sacubitril (+valsartan)
Other	Sparsentan
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

v t e Angiotensin receptor modulators
ATRTooltip Angiotensin receptor	Agonists:Angiotensin II Angiotensin III Angiotensin IV L-163,491 Saralasin Antagonists:Abitesartan Azilsartan Candesartan Elisartan Embusartan Eprosartan EXP-3174 Fimasartan Forasartan Irbesartan Losartan Milfasartan Olmesartan Olodanrigan PD123319 Pomisartan Pratosartan Ripisartan Saprisartan Sparsentan Tasosartan Telmisartan Valsartan Zolasartan ACE inhibitors:Alacepril Benazepril Captopril Cilazapril Delapril Enalapril Enalaprilat Fosinopril Gemopatrilat Imidapril Lisinopril Moexipril Omapatrilat Perindopril Quinapril Quinaprilat Ramipril Rentiapril Rescinnamine Spirapril Spiraprilat Temocapril Trandolapril Zofenopril Zofenoprilat Renin inhibitors:Aliskiren Ciprokiren Ditekiren Enalkiren Imarikiren Pepstatin Remikiren Terlakiren Zankiren Propeptides:Angiotensinogen Angiotensin I
Combinations:	Amlodipine/valsartan Olmesartan/amlodipine Olmesartan/amlodipine/hydrochlorothiazide Valsartan/hydrochlorothiazide Valsartan/hydrochlorothiazide/amlodipine

Angiotensin receptor modulators

ATRTooltip Angiotensin receptor

Propeptides:Angiotensinogen
Angiotensin I

Combinations:

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