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Safety Information

PZ0170

Sigma-Aldrich

Torcetrapib

≥98% (HPLC)

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

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About This Item

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

Cholesteryl ester transfer protein (CETP) inhibitor.
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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000227243
0000087590
0000087591
0000227243
0000087591

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Alexander J M Rennings et al.
Expert opinion on investigational drugs, 17(10), 1589-1597 (2008-09-24)
Despite reduction in low-density lipoprotein cholesterol, there is still a considerable amount of residual atherosclerosis-related disease. Epidemiological and pathophysiological data strongly favour increasing plasma high-density lipoprotein (HDL) cholesterol levels as antiatherogenic therapy, for example with cholesteryl ester transfer inhibition (CETP).
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
Raphaël Duivenvoorden et al.
Current opinion in lipidology, 23(6), 518-524 (2012-09-27)
Cholesteryl ester transfer protein (CETP)-inhibiting drugs effectively raise HDL cholesterol. In 2007, the CETP inhibitor torcetrapib unexpectedly showed increased fatality and cardiovascular events, possibly related to increased blood pressure and aldosterone levels caused by torcetrapib. Since then, novel CETP inhibiting
Douglas G Johns et al.
Drugs, 72(4), 491-507 (2012-02-24)
Lowering of serum low-density lipoprotein cholesterol (LDL-C) levels remains the primary aim of lipid management. Much progress has been made in reducing rates of cardiovascular disease morbidity and mortality, largely through increased awareness of lipid-lowering therapies and particularly through the
Stephen J Nicholls
Current cardiology reports, 14(3), 245-250 (2012-03-01)
Considerable attention focuses on the ability to develop therapeutic agents that elevate levels of high-density lipoprotein cholesterol (HDL-C). Cholesteryl ester transfer protein (CETP) inhibitors have been developed on the basis of their ability to raise HDL-C to a greater extent
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