sodium (3R,5S)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate hydrate

• ChemBase ID: 155064
• Molecular Formular: C24H27FNNaO5
• Molecular Mass: 451.4630532
• Monoisotopic Mass: 451.17709547
• SMILES: CC(C)n1c2ccccc2c(c1/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)c1ccc(cc1)F.O.[Na+]
• Canonical SMILES: [O-]C(=O)C[C@@H](C[C@@H](/C=C/c1c(c2ccc(cc2)F)c2c(n1C(C)C)cccc2)O)O.O.[Na+]
• InChI: InChI=1S/C24H26FNO4.Na.H2O/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30;;/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30);;1H2/q;+1;/p-1/t18-,19-;;/m1../s1
• InChIKey: KKEMYLLTGGQWCE-BAMQSBMESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5S)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate hydrate
• IUPAC Traditional name: sodium (3R,5S)-7-[3-(4-fluorophenyl)-1-isopropylindol-2-yl]-3,5-dihydroxyhept-6-enoate hydrate
• Synonyms: (±)-(3R*,5S*,6E)-7-[3-(4-Fluorophenyl)-1-(1-methyethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid sodium salt hydrate; Fluvastatin sodium hydrate

Database IDs

• MDL Number: MFCD20488050
• PubChem SID: 162249202
• PubChem CID: 71312069

CALCULATED PROPERTIES

• Acid pKa: 4.55701
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.837187
• LogD (pH = 7.4): 1.0636245
• Log P: 3.8259492
• Molar Refractivity: 125.6924 cm^3
• Polarizability: 45.93319 Å^3
• Polar Surface Area: 85.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥9 mg/mL
• Apperance: white to tan powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C24H25FNO4 ·Na · xH2O

DETAILS

Sigma Aldrich - SML0038

Biochem/physiol Actions
Fluvastatin is a competitive inhibitor of hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase, the enzyme that catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Fluvastatin is antilipemic and is used to reduce plasma cholesterol levels and prevent cardiovascular disease.