calcium bis((5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate) trihydrate

• ChemBase ID: 179688
• Molecular Formular: C66H74CaF2N4O13
• Molecular Mass: 1209.3875664
• Monoisotopic Mass: 1208.48463587
• SMILES: c1(c(n(c(c1c1ccccc1)c1ccc(cc1)F)CC[C@H](CC(CC(=O)[O-])O)O)C(C)C)C(=O)Nc1ccccc1.c1(c(n(c(c1c1ccccc1)c1ccc(cc1)F)CC[C@H](CC(CC(=O)[O-])O)O)C(C)C)C(=O)Nc1ccccc1.[Ca+2].O.O.O
• Canonical SMILES: O[C@@H](CC(CC(=O)[O-])O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1.O[C@@H](CC(CC(=O)[O-])O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1.O.O.O.[Ca+2]
• InChI: InChI=1S/2C33H35FN2O5.Ca.3H2O/c2*1-21(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;;;;/h2*3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40);;3*1H2/q;;+2;;;/p-2/t2*26-,27?;;;;/m11..../s1
• InChIKey: SHZPNDRIDUBNMH-INLVCVPQSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: calcium bis((5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate) trihydrate
• IUPAC Traditional name: calcium bis((5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate) trihydrate
• Synonyms: Lipitor; Torvast; Totalip; Xarator; Atorvastatin Calcium

Database IDs

• CAS Number: 134523-03-8
• PubChem SID: 164235598
• PubChem CID: 51052071

CALCULATED PROPERTIES

• Acid pKa: 4.3280535
• H Acceptors: 5
• 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: 24
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: HMG-CoA reductase inhibitor

Product Information

• Salt Data: Ca2+, 3 H2O
• Application(s): Antihypercholesterolaemic agent

REFERENCES

• Shaw, M.K. et al., Biochem. Biophys. Res. Commun., 1990, 170, 726, (pharmacol)
• Eur. Pat., 1991, Warner-Lambert, 409 281; CA, 115, 29107u, (synth, pharmacol)
• Roth, B.D. et al., J. Med. Chem., 1991, 34, 357; 463, (synth)
• Baumann, K.L. et al., Tet. Lett., 1992, 33, 2279; 2283, (synth, pmr)
• Kearney, A.S. et al., Pharm. Res., 1993, 10, 1461, (props)
• Dostal, L.A. et al., Teratology, 1994, 50, 387, (tox)
• Auerbach, B.J. et al., Atherosclerosis (Amsterdam), 1995, 115, 173, (pharmacol)
• Lea, A.P. et al., Drugs, 1997, 54, 828-847, (rev)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1268