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PZ0170

Sigma-Aldrich

Torcetrapib

≥98% (HPLC)

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Synonym(s):
(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
Empirical Formula (Hill Notation):
C26H25F9N2O4
CAS Number:
262352-17-0
Molecular Weight:
600.47
MDL number:
MFCD09260777
UNSPSC Code:
12352200
PubChem Substance ID:
329823744
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D >-70°

color

white

solubility

DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

CCOC(=O)N1[C@H](CC)C[C@H](N(Cc2cc(cc(c2)C(F)(F)F)C(F)(F)F)C(=O)OC)c3cc(ccc13)C(F)(F)F

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

InChI key

CMSGWTNRGKRWGS-NQIIRXRSSA-N

Application

Torcetrapib has been used as a reference standard in the medium chain-lipid based formulations.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Philip J Barter et al.
Journal of lipid research, 53(11), 2436-2442 (2012-09-04)
Development of the cholesteryl ester transfer protein (CETP) inhibitor, torcetrapib, was halted after the ILLUMINATE trial revealed an increase in both all-cause mortality (ACM) and major cardiovascular events (MCVEs) associated with its use. We now report that the harm caused
Shengjun Fan et al.
BMC systems biology, 6, 152-152 (2012-12-12)
Torcetrapib, a cholesteryl ester transfer protein (CETP) inhibitor which raises high-density lipoprotein (HDL) cholesterol and reduces low-density lipoprotein (LDL) cholesterol level, has been documented to increase mortality and cardiac events associated with adverse effects. However, it is still unclear the
Anatol Kontush et al.
Nature clinical practice. Cardiovascular medicine, 5(6), 329-336 (2008-04-24)
Subnormal levels of HDL cholesterol constitute a major cardiovascular risk factor. Inhibitors of cholesteryl ester transfer protein (CETP) are presently the most potent HDL-raising agents. Torcetrapib was the first CETP inhibitor to enter a large-scale, prospective, placebo-controlled interventional trial, which
Philip J Barter et al.
Circulation, 124(5), 555-562 (2011-08-02)
High-density lipoproteins have antidiabetic properties in vitro. Furthermore, elevated high-density lipoprotein levels accompanying a genetic deficiency of cholesteryl ester transfer protein are associated with decreased levels of plasma glucose. We now investigate effects on glucose homeostasis of inhibiting cholesteryl ester
Margaret R Diffenderfer et al.
Journal of lipid research, 53(6), 1190-1199 (2012-04-05)
Cholesteryl ester transfer protein (CETP) facilitates the transfer of HDL cholesteryl ester to triglyceride-rich lipoproteins (TRL). This study aimed to determine the effects of CETP inhibition with torcetrapib on TRL composition and apoB-48 metabolism. Study subjects with low HDL cholesterol
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