Cilazapril

Base Information

• Chemical Name: Cilazapril
• CAS No.: 88768-40-5
• Molecular Formula: C22H31N3O5
• Molecular Weight: 417.505
• European Community (EC) Number: 641-006-9
• UNII: 8Q9454114Q
• DSSTox Substance ID: DTXSID1048629
• Nikkaji Number: J33.155D
• Wikipedia: Cilazapril
• Wikidata: Q867350
• NCI Thesaurus Code: C76134
• Pharos Ligand ID: Q7XCQ3KPXJ3S
• Metabolomics Workbench ID: 43506
• ChEMBL ID: CHEMBL515606
• Mol file: 88768-40-5.mol

Synonyms:Cilazapril;Cilazapril Anhydrous;Cilazapril Hydrate;Cilazapril Monohydrate;Cilazapril Monohydrobromide;Cilazapril, (S*)-Isomer;Cilazapril, Anhydrous;Inhibace;Ro 31 2848;Ro 31-2848;Ro 312848;Ro-31-2848;Ro312848

Chemical Property of Cilazapril

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 3.73E-15mmHg at 25°C
• Melting Point: 95-97 °C
• Refractive Index: 1.591
• Boiling Point: 598.1 °C at 760 mmHg
• Flash Point: 315.5 °C
• PSA: 99.18000
• Density: 1.26 g/cm³
• LogP: 1.86220
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 417.22637110
• Heavy Atom Count: 30
• Complexity: 608

Purity/Quality:

99% ^*data from raw suppliers

Cilazapril ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC2CCCN3CCCC(N3C2=O)C(=O)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCCN3CCC[C@H](N3C2=O)C(=O)O
• Description: Cilazapril is a prodrug form of the angiotensin converting enzyme (ACE) inhibitor cilazaprilat. In vivo, cilazapril (0.1 mg/kg) inhibits plasma ACE activity and inhibits the angiotensin I-induced pressor response in anesthetized rats and cats. It decreases systolic blood pressure in spontaneously hypertensive rats when administered at a dose of 30 mg/kg. Cilazapril (10 mg/kg, p.o.) decreases blood pressure in volume-depleted renal hypertensive dogs. Formulations containing cilazapril have been used in the treatment of hypertension.
• Uses: An ACE inhibitor. Hydrolyzed in vivo to the active diacid metabolite (Cilazaprilat). Antihypertensive An ACE inhibitor. Hydrolyzed in vivo to the active diacid metabolite (Cilazaprilat). Antihypertensive.

Technology Process of Cilazapril

There total 15 articles about Cilazapril which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

(1S,9S)-t-butyl 9-<(1S)-ethoxycarbonyl-3-phenylpropylamino>octahydro-10-oxo-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate (106860-19-9) → cilazapril (88768-40-5,106928-09-0)

Guidance literature:

With hydrogenchloride; In dichloromethane; for 16h; Ambient temperature;

Reference yield: 86.73%

C26H41N5O4 → cilazapril (88768-40-5,106928-09-0)

Guidance literature:

C₂₆H₄₁N₅O₄; With acetic acid; In water; at 20 ℃; for 4 - 5h;

With 4-methyl-morpholine; (R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester; In toluene; at 75 - 80 ℃; for 15h;

With hydrogenchloride; In dichloromethane; at -5 - 0 ℃; for 6h;

Reference yield: 85.0%

→ cilazapril (88768-40-5,106928-09-0)

Guidance literature:

Purification / work up;

upstream raw materials:

(1S,9S)-t-butyl 9-<(1S)-ethoxycarbonyl-3-phenylpropylamino>octahydro-10-oxo-6H-pyridazino<1,2-a><1,2>diazepine-1-carboxylate

(R)-2-hydroxy4-phenylbutanoic acid

ethyl (R)-2-hydroxy-4-phenylbutyrate

ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate

Downstream raw materials:

ethanol

cilazaprilat

Refernces

• 1、 -. "A NOVEL PROCESS FOR THE PREPARATION OF CILAZAPRIL". Page 4-5. . Retrieved 2008/06/13.
• 2、 Attwood, Michael R.,Hassall, Cedric H.,Kroehn, Antonin,Lawton, Geoffrey,Redshaw, Sally. "The Design and Synthesis of the Angiotensin Converting Enzyme Inhibitor Cilazapril and Related Bicyclic Compounds". . p. 1011 - 1020. Retrieved 2007/10/02.