(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

• ChemBase ID: 1172
• Molecular Formular: C22H31N3O5
• Molecular Mass: 417.49864
• Monoisotopic Mass: 417.22637111
• SMILES: O=C1N2N(CCC[C@H]2C(=O)O)CCC[C@@H]1N[C@@H](CCc1ccccc1)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H]1CCCN2N(C1=O)[C@@H](CCC2)C(=O)O)CCc1ccccc1
• 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
• InChIKey: HHHKFGXWKKUNCY-FHWLQOOXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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
• IUPAC Traditional name: inhibace
• Synonyms: Inhibace; Cilazapril; (1S,9S)-9-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]octahydro-10-oxo-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic Acid; Ro 31-2848; Vascace; Yipingshu

Database IDs

• CAS Number: 92077-78-6; 88768-40-5
• PubChem SID: 160964635
• PubChem CID: 56330

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4099488
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.26813108
• LogD (pH = 7.4): -1.4383031
• Log P: -0.007882288
• Molar Refractivity: 110.5637 cm^3
• Polarizability: 43.8066 Å^3
• Polar Surface Area: 99.18 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.2
• LOG S: -2.59
• Solubility (Water): 1.06e+00 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 95-97°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB01340

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: Cilazapril is an ACE inhibtor class drug used in the treatment of hypertension and heart failure.
• 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.
• External Links: Wikipedia

Toronto Research Chemicals - C441200

An ACE inhibitor. Hydrolyzed in vivo to the active diacid metabolite (Cilazaprilat). Antihypertensive.

REFERENCES

• Natoff, I.L., et al.: J. Cardiovasc. Pharmacol., 7, 569 (1985)
• Szucs, T., et al.: Drugs, 41, Suppl.1, 18 (1985)
• Pordy, R.C., et al.: Cardiology, 86, 41 (1985)