sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-[(1,1,1,3,3,3-2H6)propan-2-yl]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate

• ChemBase ID: 177606
• Molecular Formular: C22H27FN3NaO6S
• Molecular Mass: 503.5194532
• Monoisotopic Mass: 503.1502291
• SMILES: c1(ccc(cc1)c1nc(nc(c1/C=C/[C@H](C[C@H](CC(=O)[O-])O)O)C(C)C)N(S(=O)(=O)C)C)F.[Na+]
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)[O-])O)/C=C/c1c(nc(nc1c1ccc(cc1)F)N(S(=O)(=O)C)C)C(C)C.[Na+]
• InChI: InChI=1S/C22H28FN3O6S.Na/c1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32;/h5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30);/q;+1/p-1/b10-9+;/t16-,17-;/m1./s1
• InChIKey: RGEBGDYYHAFODH-DHMAKVBVSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-[(1,1,1,3,3,3-^2H₆)propan-2-yl]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate
• IUPAC Traditional name: sodium (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-[(1,1,1,3,3,3-^2H₆)propan-2-yl]pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate
• Synonyms: 7-[4-(4-Fluorophenyl)-6-(1-methylethyl-d6)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoic Acid Sodium Salt; Rosuvastatin-d6 Sodium Salt

Database IDs

• PubChem SID: 164233516
• PubChem CID: 71752109

CALCULATED PROPERTIES

• Acid pKa: 4.0000324
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.4135099
• LogD (pH = 7.4): -1.2360909
• Log P: 1.9229605
• Molar Refractivity: 132.2754 cm^3
• Polarizability: 48.024994 Å^3
• Polar Surface Area: 143.75 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-white solid
• Melting Point: >95°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R700502

Labelled Rosuvastatin (R700500), a selective, competitive HMG-CoA reductase inhibitor.

REFERENCES

• Watanabe, M., et al.: Bioorg. Med. Chem., 5, 437 (1997)
• Lee, E., et al.: Clin. Pharmacol. Ther., 78, 330 (1997)
• Ferdinand, K.C., et al.: Am. J. Cardiol., 97, 229 (1997)