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Cilazapril

Cilazapril

Synopsis, Chemistry

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Also known as: 88768-40-5, Cilazapril anhydrous, Inhibace, Cilazaprilum, Vascace, Cilazapril (anhydrous)

Molecular Formula

C₂₂H₃₁N₃O₅

Molecular Weight

417.5 g/mol

InChI Key

HHHKFGXWKKUNCY-FHWLQOOXSA-N

FDA UNII

8Q9454114Q

One of the ANGIOTENSIN-CONVERTING ENZYME INHIBITORS (ACE inhibitors) used for hypertension. It is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat.

1 2D Structure

Cilazapril

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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)/t17-,18-,19-/m0/s1

2.1.3 InChI Key

HHHKFGXWKKUNCY-FHWLQOOXSA-N

2.1.4 Canonical SMILES

CCOC(=O)C(CCC1=CC=CC=C1)NC2CCCN3CCCC(N3C2=O)C(=O)O

2.1.5 Isomeric SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCCN3CCC[C@H](N3C2=O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

8Q9454114Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cilazapril Anhydrous

2. Cilazapril Hydrate

3. Cilazapril Monohydrate

4. Cilazapril Monohydrobromide

5. Cilazapril, (s*)-isomer

6. Cilazapril, Anhydrous

7. Inhibace

8. Ro 31 2848

9. Ro 31-2848

10. Ro 312848

11. Ro-31-2848

12. Ro312848

2.3.2 Depositor-Supplied Synonyms

1. 88768-40-5

2. Cilazapril Anhydrous

3. Inhibace

4. Cilazaprilum

5. Vascace

6. Cilazapril (anhydrous)

7. Dynorm

8. Cilazapril Hydrate

9. Cilazapril [inn]

10. Ro 34-2848

11. Anhydrous Cilazapril

12. Cilazapril (inn)

13. Inhibace (tn)

14. 6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic Acid, 9-(((1s)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)octahydro-10-oxo-, (1s,9s)-

15. Initiss

16. (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

17. Ncgc00182039-01

18. Cilazaprilum [latin]

19. Ro-312848006

20. 8q9454114q

21. Cilazil

22. Inibace

23. Vascase

24. Unii-8q9454114q

25. Ro-312848

26. Cilazapril [mi]

27. Cilazapril [vandf]

28. Cilazapril [who-dd]

29. Dsstox_cid_28555

30. Dsstox_rid_82827

31. Dsstox_gsid_48629

32. Schembl24962

33. Chebi:3698

34. Chembl515606

35. Gtpl6459

36. Dtxsid1048629

37. Hy-a0043

38. Zinc3781951

39. Tox21_112971

40. Ac-269

41. Akos015951168

42. Db01340

43. Ro34-2848

44. Ncgc00182039-02

45. Ro-34-2848

46. (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

47. 6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic Acid, 9-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)octahydro-10-oxo-, (1s-(1alpha,9alpha(r*)))-

48. 6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylicacid, 9-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-,(1s,9s)-

49. Cas-88768-40-5

50. Ro 31-2848006

51. D07699

52. Ab01565812_02

53. 768c405

54. A916338

55. Q867350

56. Ro-31-2848/006

57. Brd-k96177243-002-01-9

58. (1s,9s)-9-(((s)-1-carboxy-3-phenylpropyl)amino)octahydro-10-oxo-6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic Acid 9-ethyl Ester

59. (1s,9s)-9-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-10-oxooctahydro-6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic Acid

60. (1s,9s)-9-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-6h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic Acid

61. (1s,9s)-9-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-10-oxo-1,2,3,4,6,7,8,9-octahydropyridazino[1,2-a]diazepine-1-carboxylic Acid

62. (1s,9s)-9-{[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1h-pyridazino[1,2-a][1,2]diazepine-1-carboxylic Acid

63. (5s,8s)-5-{[(1s)-1-ethoxycarbonyl-3-phenyl-propyl]-amino}-6-oxo-1,7-diazabicyclo[5.4.0]undecane-8-carboxylic Acid

64. 6h-pyridazino(1,2-a)(1,2)diazepine-1-carboxylic Acid, 9-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)octahydro-10-oxo-, Monohydrate, (1s-(1.alpha.,9.alpha.(r*)))

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₁N₃O₅
Molecular Weight	417.5 g/mol
XLogP3	0.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	9
Exact Mass	417.22637110 g/mol
Monoisotopic Mass	417.22637110 g/mol
Topological Polar Surface Area	99.2 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	608
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Cilazapril is an ACE inhibtor class drug used in the treatment of hypertension and heart failure.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cilazapril inhibits the production angiotensin II. By doing so, it decreases sodium and water reabsorption (via aldosterone) and it decreases vasoconstriction. The combined effect of this is a decrease in vascular resistance, and therefore, blood pressure. The absolute bioavailability of cilazaprilat after oral administration of cilazapril is 57% based on urinary recovery data. (The absolute bioavailability of cilazaprilat after oral administration of cilazaprilat is 19%.) Ingestion of food immediately before the administration of cilazapril reduces the average peak plasma concentration of cilazaprilat by 29%, delays the peak by one hour and reduces the bioavailability of cilazaprilat by 14%. These pharmacokinetic changes have little influence on plasma ACE inhibition.

5.2 MeSH Pharmacological Classification

Angiotensin-Converting Enzyme Inhibitors

A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. (See all compounds classified as Angiotensin-Converting Enzyme Inhibitors.)

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

5.3 ATC Code

C09AA08

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C09 - Agents acting on the renin-angiotensin system

C09A - Ace inhibitors, plain

C09AA - Ace inhibitors, plain

C09AA08 - Cilazapril

5.4 Absorption, Distribution and Excretion

Absorption

Maximum plasma concentrations of cilazaprilat are reached within two hours after administration of cilazapril.

Route of Elimination

Cilazaprilat is eliminated unchanged by the kidneys. The total urinary recovery of cilazaprilat after intravenous administration of 2.5 mg is 91%.

Clearance

Total clearance is 12.3 L/h and renal clearance is 10.8 L/h. The total urinary recovery of cilazaprilat following the oral administration of 2.5 mg cilazapril is 52.6%.

5.5 Biological Half-Life

Half-lives for the periods 1 to 4 hours and 1 to 7 days after the intravenous administration of 2.5 mg cilazaprilat are 0.90 and 46.2 hours respectively.

5.6 Mechanism of Action

Cilazapril is a pyridazine ACE inhibitor. It competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. As angiotensin II is a vasoconstrictor and a negative feedback mediator for renin activity, lower angiotensin II levels results in a decrease in blood pressure, an increase in renin activity, and stimulation of baroreceptor reflex mechanisms. Kininase II, an enzyme which degrades the vasodilator bradykinin, is identical to ACE and may also be inhibited.