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

• ChemBase ID: 160865
• Molecular Formular: C33H34FN2NaO5
• Molecular Mass: 580.6216332
• Monoisotopic Mass: 580.2349447
• SMILES: c1(c(c(n(c1C(C)C)CC[C@@H](C[C@@H](CC(=O)[O-])O)O)c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1.[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)Nc1ccccc1.[Na+]
• InChI: InChI=1S/C33H35FN2O5.Na/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)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-;/m0./s1
• InChIKey: VVRPOCPLIUDBSA-WMXJXTQLSA-M

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 501121-34-2
• PubChem SID: 162255000
• PubChem CID: 46780491

CALCULATED PROPERTIES

• H Donor: 3
• LogD (pH = 5.5): 4.188813
• LogD (pH = 7.4): 2.444739
• Log P: 5.387147
• Molar Refractivity: 169.0355 cm^3
• Polarizability: 62.080032 Å^3
• Polar Surface Area: 114.62 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false
• Acid pKa: 4.3280535
• H Acceptors: 5

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White Solid
• Melting Point: 182-184°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A791735

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

REFERENCES

• Kearney, A.S., et al.: Pharm. Res., 10, 1461 (1993)
• Heinonen, T.M., et al.: Clin. Ther., 18. 853 (1993)
• Whitfield, L.R., et al.: Eur. J. Drug Metab. Pharmacokinet., 25, 97 (2000)