ethyl (2R,4S)-4-({[3,5-bis(trifluoromethyl)phenyl]methyl}(methoxycarbonyl)amino)-2-ethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate

• ChemBase ID: 129947
• Molecular Formular: C26H25F9N2O4
• Molecular Mass: 600.4733288
• Monoisotopic Mass: 600.16706127
• SMILES: FC(F)(F)c1cc(cc(c1)C(F)(F)F)CN(C(=O)OC)[C@@H]1c2c(ccc(c2)C(F)(F)F)N(C(=O)OCC)[C@@H](C1)CC
• Canonical SMILES: CCOC(=O)N1[C@H](CC)C[C@@H](c2c1ccc(c2)C(F)(F)F)N(C(=O)OC)Cc1cc(cc(c1)C(F)(F)F)C(F)(F)F
• InChI: InChI=1S/C26H25F9N2O4/c1-4-18-12-21(19-11-15(24(27,28)29)6-7-20(19)37(18)23(39)41-5-2)36(22(38)40-3)13-14-8-16(25(30,31)32)10-17(9-14)26(33,34)35/h6-11,18,21H,4-5,12-13H2,1-3H3/t18-,21+/m1/s1
• InChIKey: CMSGWTNRGKRWGS-NQIIRXRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R,4S)-4-({[3,5-bis(trifluoromethyl)phenyl]methyl}(methoxycarbonyl)amino)-2-ethyl-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate
• IUPAC Traditional name: torcetrapib
• Synonyms: (2R,4S)-4-[[[3,5-Bis(trifluoromethyl)phenyl]methyl](methoxycarbonyl)amino]-2-ethyl-3,4-dihydro-6-(trifluoromethyl)-1(2H)-quinolinecarboxylic Acid Ethyl Ester; (-)-Torcetrapib; CP 529414; (2R,4S)-4-((3,5-Bis-trifluoromethylbenzyl)methoxycarbonylamino)-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester; CP-529,414; CP-529414; Torcetrapib; Torcetrapib

Database IDs

• CAS Number: 262352-17-0
• MDL Number: MFCD09260777
• PubChem SID: 162224233
• PubChem CID: 159325
• CHEBI ID: 49203
• CHEMBL: 479527
• Chemspider ID: 140123
• KEGG ID: D06195
• Wikipedia Title: Torcetrapib

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 7.0840216
• LogD (pH = 7.4): 7.0840216
• Log P: 7.0840216
• Molar Refractivity: 128.8897 cm^3
• Polarizability: 47.115524 Å^3
• Polar Surface Area: 59.08 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >5 mg/mL; Methanol
• Apperance: Off-White Low Melting Solid; white powder
• Optical Rotation: [α]/D >-70°

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C26H25F9N2O4

DETAILS

Sigma Aldrich - PZ0170

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Torcetrapib is a Cholesteryl ester transfer protein (CETP) inhibitor. CETP normally transfers cholesterol from HDL cholesterol to very low density or low density lipoproteins (VLDL or LDL). Inhibition of this process results in higher HDL levels (the "good" cholesterol-containing particle) and reduces LDL levels (the "bad" cholesterol). Unfortunately clinical trials were stopped because of excessive all cause mortality. Reasons are still being investigated, but may be related to some off target effects such as an increase in aldosterone secretion not found in some other CETP inhibitors.

Toronto Research Chemicals - T546500

Cholesteryl ester transfer protein (CETP) inhibitor. Antilipemic; antiatherosclerotic.

REFERENCES

• Burnett, J.R., et al.: Curr. Opin. Invest. Drugs, 6, 944 (2005)
• Clark, R.W., et al.: J. Lipid Res., 47, 537 (2005)