disodium (3R,5R)-7-[2-(4-fluorophenyl)-4-[(4-oxidophenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 170258
• Molecular Formular: C33H33FN2Na2O6
• Molecular Mass: 618.6028632
• Monoisotopic Mass: 618.21180357
• SMILES: c1(c(n(c(c1C(=O)Nc1ccc(cc1)[O-])C(C)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)c1ccc(cc1)F)c1ccccc1.[Na+].[Na+]
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)[O-])O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccc(cc1)[O-].[Na+].[Na+]
• InChI: InChI=1S/C33H35FN2O6.2Na/c1-20(2)31-30(33(42)35-24-12-14-25(37)15-13-24)29(21-6-4-3-5-7-21)32(22-8-10-23(34)11-9-22)36(31)17-16-26(38)18-27(39)19-28(40)41;;/h3-15,20,26-27,37-39H,16-19H2,1-2H3,(H,35,42)(H,40,41);;/q;2*+1/p-2/t26-,27-;;/m1../s1
• InChIKey: LTONRNZYFYCVRP-AJUXDCMMSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (3R,5R)-7-[2-(4-fluorophenyl)-4-[(4-oxidophenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: disodium (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-4-[(4-oxidophenyl)carbamoyl]-3-phenylpyrrol-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR,δR)-2-(4-Fluorophenyl)-β,δ-dihydroxy-4-[[(4-hydroxyphenyl)amino]carbonyl]-5-(1-methylethyl)-3-phenyl-1H-pyrrole-1-heptanoic Acid Disodium Salt; BMS 241423-01; PD 142542; p-Hydroxyatorvastatin Disodium Salt; 4-Hydroxy Atorvastatin Disodium Salt

Database IDs

• CAS Number: 1276537-18-8
• PubChem SID: 164226168
• PubChem CID: 45039408

CALCULATED PROPERTIES

• Acid pKa: 4.3280535
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.8852012
• LogD (pH = 7.4): 2.1372104
• Log P: 5.0835814
• Molar Refractivity: 181.5667 cm^3
• Polarizability: 62.413193 Å^3
• Polar Surface Area: 137.68 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: >175°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - H828960

A metabolite of Atorvastatin, a selective, competitive HMG-CoA reductase inhibitor. Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia.

REFERENCES

• Smith, S., et al.: Am. J. Cardiol., 80, 10H (1997)
• Jacobsen, W., et al.: Drug Metab. Dispos., 28, 1369 (1997)
• Istvan, E., et al.: Science, 292, 1160 (1997)
• Tabernero, L., et al.: J. Biol. Chem., 278, 19933 (1997)
• Bratton, L., et al.: Bioorg. Med. Chem