(2R,6R,9S)-9-[(2S)-2-(acetylsulfanyl)-3-methylbutanamido]-8-oxo-7-azatricyclo[9.4.0.02,7]pentadeca-1(11),12,14-triene-6-carboxylic acid

• ChemBase ID: 171522
• Molecular Formular: C22H28N2O5S
• Molecular Mass: 432.53312
• Monoisotopic Mass: 432.17189301
• SMILES: C1[C@H]2N([C@H](CC1)C(=O)O)C(=O)[C@H](Cc1c2cccc1)NC(=O)[C@H](C(C)C)SC(=O)C
• Canonical SMILES: CC(=O)S[C@H](C(=O)N[C@H]1Cc2ccccc2[C@@H]2N(C1=O)[C@H](CCC2)C(=O)O)C(C)C
• InChI: InChI=1S/C22H28N2O5S/c1-12(2)19(30-13(3)25)20(26)23-16-11-14-7-4-5-8-15(14)17-9-6-10-18(22(28)29)24(17)21(16)27/h4-5,7-8,12,16-19H,6,9-11H2,1-3H3,(H,23,26)(H,28,29)/t16-,17+,18+,19-/m0/s1
• InChIKey: FXKFFTMLFPWYFH-MANSERQUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,6R,9S)-9-[(2S)-2-(acetylsulfanyl)-3-methylbutanamido]-8-oxo-7-azatricyclo[9.4.0.0^2,^7]pentadeca-1(11),12,14-triene-6-carboxylic acid
• IUPAC Traditional name: (2R,6R,9S)-9-[(2S)-2-(acetylsulfanyl)-3-methylbutanamido]-8-oxo-7-azatricyclo[9.4.0.0^2,^7]pentadeca-1(11),12,14-triene-6-carboxylic acid
• Synonyms: (4S,7S,12bR)-7-[[(2S)-2-(Acetylthio)-3-methyl-1-oxobutyl]amino]-1,2,3,4,6,7,8,12b-octahydro-6-oxo-pyrido[2,1-a][2]benzazepine-4-carboxylic Acid; AVE-7688; Ilepatril

Database IDs

• CAS Number: 473289-62-2
• PubChem SID: 164227432
• PubChem CID: 71749452

CALCULATED PROPERTIES

• Acid pKa: 3.5993142
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.5155844
• LogD (pH = 7.4): -0.9316792
• Log P: 2.4116037
• Molar Refractivity: 113.1589 cm^3
• Polarizability: 44.485023 Å^3
• Polar Surface Area: 103.78 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - I266500

A dual angiotensin-converting enzyme and neutral endopeptidase inhibitor, for the potential treatment of hypertension and diabetic nephropathy. Ilepatril is currently in phase IIb/III clinical trials for hypertension and phase II trials for diabetic nephr

REFERENCES

• Tabrizchi, R., et al.: Drugs, 63, 2185 (2003)
• Azizi, M., et al.: Clin. Pharmacol. Ther., 79 49 (2003)
• Davidson, E., et al.: Diabetes, 56, 355 (2003)
• Del Colle, S., et al.: J. Cardiovasc. Pharmacol., 50, 487 (2003)