sodium (3R,5R)-7-[5-(4-fluorophenyl)-2-oxo-4-phenyl-3-(phenylcarbamoyl)-3-(propan-2-yl)-2,3-dihydro-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 160742
• Molecular Formular: C33H34FN2NaO6
• Molecular Mass: 596.6210332
• Monoisotopic Mass: 596.22985932
• SMILES: C1(=C(N(C(=O)C1(C(=O)Nc1ccccc1)C(C)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)c1ccc(cc1)F)c1ccccc1.[Na+]
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)[O-])O)CCN1C(=C(C(C1=O)(C(C)C)C(=O)Nc1ccccc1)c1ccccc1)c1ccc(cc1)F.[Na+]
• InChI: InChI=1S/C33H35FN2O6.Na/c1-21(2)33(31(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)30(23-13-15-24(34)16-14-23)36(32(33)42)18-17-26(37)19-27(38)20-28(39)40;/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40);/q;+1/p-1/t26-,27-,33?;/m1./s1
• InChIKey: AWDUSRYVYMXRPW-LGZZEMPASA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5R)-7-[5-(4-fluorophenyl)-2-oxo-4-phenyl-3-(phenylcarbamoyl)-3-(propan-2-yl)-2,3-dihydro-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: sodium (3R,5R)-7-[5-(4-fluorophenyl)-3-isopropyl-2-oxo-4-phenyl-3-(phenylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR,δR)-5-(4-Fluorophenyl)-2,3-dihydro-β,δ-dihydroxy-3-(1-methylethyl)-2-oxo-4-phenyl-3-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic Acid Sodium Salt; Atorvastatin Lactam Sodium Salt Impurity

Database IDs

• CAS Number: 148217-40-7
• PubChem SID: 162254877
• PubChem CID: 71313455

CALCULATED PROPERTIES

• Acid pKa: 3.987573
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.264063
• LogD (pH = 7.4): 0.61932427
• Log P: 3.7854793
• Molar Refractivity: 169.0207 cm^3
• Polarizability: 60.02998 Å^3
• Polar Surface Area: 130.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 133-136°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A791775

A photodegradation product of Atorvastatin (a cyclic impurity of Atorvastatin).

REFERENCES

• Roger, D., et al.: Clin. Exp. Dermatol., 19, 88 (1994)
• Cosa, G., et al.: Photochem. Photobiol., 80, 159 (1994)
• Kerwin, B., et al.: J. Pharm. Sci., 96, 1468 (1994)