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

• ChemBase ID: 177605
• Molecular Formular: C44H54CaF2N6O12S2
• Molecular Mass: 1001.1373664
• Monoisotopic Mass: 1000.28351062
• 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.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.[Ca+2]
• 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.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.[Ca+2]
• InChI: InChI=1S/2C22H28FN3O6S.Ca/c2*1-13(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;/h2*5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30);/q;;+2/p-2/b2*10-9+;/t2*16-,17-;/m11./s1
• InChIKey: LALFOYNTGMUKGG-BGRFNVSISA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: calcium bis((3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate)
• IUPAC Traditional name: calcium bis((3R,5S,6E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethanesulfonamido)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate); calcium bis((3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate)
• Synonyms: Rosuvastatin calcium; (3R,5S,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3,5-dihydroxy-6-heptenoic Acid Calcium Salt; Crestor; ZD 4522 Calcium Salt; Rosuvastatin Hemicalcium; Rosuvastatin Calcium; Fortius; Rostar; S 4522; Rosuvastatin Calcium Salt; Rosuvastatin Calcium

Database IDs

• CAS Number: 147098-20-2
• PubChem SID: 164233515
• PubChem CID: 5282455

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: 48.024193 Å^3
• Polar Surface Area: 143.75 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 151-156°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Mechanism of Action: Hypolipidaemic HMG-CoA reductase inhibitor

Product Information

• Purity: 95+%
• Salt Data: Ca2+
• Application(s): Antihypercholesterolemic; preventing cardiovascular diseases

DETAILS

Toronto Research Chemicals - R700500

A selective, competitive HMG-CoA reductase inhibitor. Antilipemic.

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)
• Eur. Pat., 1993, Shionogi, 521 471; CA, 118, 254949b, (synth, pharmacol)
• Watanabe, M. et al., Bioorg. Med. Chem., 1997, 5, 437-444, (synth, pharmacol)
• Graul, A. et al., Drugs of the Future, 1999, 24, 511-513, (rev)
• McTaggart, F. et al., Am. J. Cardiol., 2001, 87, 28B-33B, (pharmacol)