Cilazapril - Misplaced Pages

Antihypertensive drug of the ACE inhibitor class

Cilazapril
Names

Preferred IUPAC name (1S,9S)-9-{amino}-10-oxooctahydro-6H-pyridazinodiazepine-1-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
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 , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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.

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

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 the renin–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, +HCT) Valsartan (+aliskiren, +amlodipine, +amlodipine and HCT, +HCT, +lercanidipine, +nebivolol, +sacubitril)
Renin inhibitors ("-kiren")	Aliskiren (+amlodipine, +HCT, +amlodipine and HCT) Remikiren
Dual ACE/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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