Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C26H25F9N2O4 |
| Molecular Weight | 600.4733 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)N1[C@H](CC)C[C@H](N(CC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)C(=O)OC)C3=CC(=CC=C13)C(F)(F)F
InChI
InChIKey=CMSGWTNRGKRWGS-NQIIRXRSSA-N
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
| Molecular Formula | C26H25F9N2O4 |
| Molecular Weight | 600.4733 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Torcetrapib is a CETP inhibitor which was developed by Pfizer for the treatment of diseases associated with elevated level of cholesterol. The drug was tested in phase III (in combination with atorvastatin) of clinical trials in coronary heart disease patients as well as in patients with hyperlipoproteinemia, hypertriglyceridemia, hypercholesterolemia, hyperlipidemia, however its development was terminated due to the high risk of death and heart problems.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3572 |
25.2 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
373 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14739125/ |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
527 ng/mL EXPERIMENT https://doi.org/10.1124/dmd.108.0231761 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
576 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18694908 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2920 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18694908 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
BISTRIFLUOROMETHYLBENZOIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3670 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14739125/ |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
5040 ng × h/mL EXPERIMENT https://doi.org/10.1124/dmd.108.0231761 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
7570 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18694908 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
452000 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18694908 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
BISTRIFLUOROMETHYLBENZOIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14739125/ |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.1 h EXPERIMENT https://doi.org/10.1124/dmd.108.0231761 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
201 h EXPERIMENT https://doi.org/10.1124/dmd.108.0231761 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
211 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18694908 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
TORCETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
117 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18694908 |
120 mg single, oral dose: 120 mg route of administration: Oral experiment type: SINGLE co-administered: |
BISTRIFLUOROMETHYLBENZOIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| yes [IC50 1.6933 uM] | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [Km 1.8 uM] | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Early changes in arterial structure and function following statin initiation: quantification by magnetic resonance imaging. | 2008-04 |
|
| Development of a self-emulsifying formulation that reduces the food effect for torcetrapib. | 2008-03-03 |
|
| Effects of the cholesteryl ester transfer protein inhibitor torcetrapib on VLDL apolipoprotein E metabolism. | 2008-03 |
|
| The conscientious judgement of a DSMB--statistical stopping rules re-examined. | 2008-01 |
|
| Inhibition of CETP by torcetrapib attenuates the atherogenicity of postprandial TG-rich lipoproteins in type IIB hyperlipidemia. | 2008-01 |
|
| Chiral bioanalysis of torcetrapib enantiomers in hamster plasma by normal-phase liquid chromatography and detection by atmospheric pressure chemical ionization tandem mass spectrometry. | 2007-12-15 |
|
| Refocusing on use of cholesteryl ester transfer protein inhibitors. | 2007-12-03 |
|
| Increasing high-density lipoprotein cholesterol, inhibition of cholesteryl ester transfer protein, and heart disease risk reduction. | 2007-12-03 |
|
| Regulatory considerations in the development of high-density lipoprotein therapies. | 2007-12-03 |
|
| Illuminating HDL--is it still a viable therapeutic target? | 2007-11-22 |
|
| Effects of torcetrapib in patients at high risk for coronary events. | 2007-11-22 |
|
| Analysis of arterial intimal hyperplasia: review and hypothesis. | 2007-10-31 |
|
| Development and validation of an enantioselective HPLC-UV method using Chiralpak AD-H to quantify (+)- and (-)-torcetrapib enantiomers in hamster plasma--application to a pharmacokinetic study. | 2007-10-01 |
|
| The withdrawal of torcetrapib from drug development: implications for the future of drugs that alter HDL metabolism. | 2007-10 |
|
| The continuing complexities of high-density lipoprotein metabolism in drug discovery and development. | 2007-09 |
|
| Does torcetrapib reduce the progression of atherosclerotic disease? | 2007-09 |
|
| A concise asymmetric synthesis of torcetrapib. | 2007-08-03 |
|
| The role of CETP inhibition in dyslipidemia. | 2007-08 |
|
| Torcetrapib and carotid intima-media thickness in mixed dyslipidaemia (RADIANCE 2 study): a randomised, double-blind trial. | 2007-07-14 |
|
| HDL cholesterol and atherosclerosis. | 2007-07-14 |
|
| Where are we with high-density lipoprotein raising and inhibition of cholesteryl ester transfer for heart disease risk reduction? | 2007-07 |
|
| 'Linkage' pharmaceutical evergreening in Canada and Australia. | 2007-06-01 |
|
| Development of torcetrapib, a lipid-lowering drug, abandoned. | 2007-06 |
|
| Inhibition of CETP activity by torcetrapib reduces susceptibility to diet-induced atherosclerosis in New Zealand White rabbits. | 2007-06 |
|
| Man on a mission. | 2007-05-31 |
|
| HDL: back to the drawing board. | 2007-05 |
|
| Where now for new drugs for atherosclerosis? | 2007-05 |
|
| World Hypertension Day 2007. | 2007-05 |
|
| Inhibition of cholesteryl ester transfer protein by torcetrapib modestly increases macrophage cholesterol efflux to HDL. | 2007-05 |
|
| Effect of torcetrapib on carotid atherosclerosis in familial hypercholesterolemia. | 2007-04-19 |
|
| New clues to HDL's benefits revealed. | 2007-04-11 |
|
| Cholesterol, cholesterol-lowering agents/statins, and urologic disease: Part VI--The recent rise and fall of the HDL-boosting drug torceptrapib. | 2007-04 |
|
| Designs of RADIANCE 1 and 2: carotid ultrasound studies comparing the effects of torcetrapib/atorvastatin with atorvastatin alone on atherosclerosis. | 2007-04 |
|
| Niacin into the void. Failure of HDL cholesterol drug may B this vitamin's big chance. | 2007-04 |
|
| Off-target properties of pharmacotherapy and the importance of mechanistic investigations in early clinical phase drug development. | 2007-04 |
|
| CETP inhibitors to increase HDL cholesterol levels. | 2007-03-29 |
|
| Effect of torcetrapib on the progression of coronary atherosclerosis. | 2007-03-29 |
|
| [Advances in the study of anti-atherosclerosis drugs]. | 2007-03 |
|
| New drug fizzles at raising HDL. Tried-and-true strategies are still excellent ways to boost good cholesterol. | 2007-03 |
|
| Identifying and attaining LDL-C goals: mission accomplished? Next target: new therapeutic options to raise HDL-C levels. | 2007-03 |
|
| The hypertension peril and drug development. | 2007-02-17 |
|
| Early termination of drug trials. | 2007-02-17 |
|
| Drug designed to raise HDL levels falls down. | 2007-02 |
|
| The failure of torcetrapib: was it the molecule or the mechanism? | 2007-02 |
|
| CETP inhibition in cardiovascular risk management: a critical appraisal. | 2007-02 |
|
| When the party's over. | 2007-01-04 |
|
| The strange case of Dr HDL and Mr HDL: does a NO's story illuminate the mystery of HDL's dark side uncovered by Dr HDL's drug targeting CETP? | 2007 |
|
| Intensive statin treatment or combination therapy in high-risk patients. | 2007 |
|
| Solving the HDL mystery. | 2006-12-18 |
|
| The potential for CETP inhibition to reduce cardiovascular disease risk. | 2006-12 |
Patents
Sample Use Guides
Patients were receiving torcetrapib at a dose 10, 30, 60, or 90 mg/day.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:18:41 GMT 2025
by
admin
on
Mon Mar 31 18:18:41 GMT 2025
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| Record UNII |
4N4457MV2U
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C29703
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262352-17-0
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TORCETRAPIB
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NN-58
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DTXSID20180873
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4N4457MV2U
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100000089212
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C483909
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159325
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DB06281
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m10978
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C91058
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CHEMBL479527
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SUB25213
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLIC ENZYME -> SUBSTRATE |
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SOLVATE->ANHYDROUS | |||
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EXCRETED UNCHANGED |
FECAL
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TARGET -> INHIBITOR |
SELECTIVE
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT |
Other peaks (M2, M6A and M6B, M7, M12, M13, M24, and M25) represented <2% of the dose
FECAL
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
Other peaks (M2, M6A and M6B, M7, M12, M13, M24, and M25) represented <2% of the dose.
FECAL
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
Other peaks (M2, M6A and M6B, M7, M12, M13, M24, and M25) represented <2% of the dose
FECAL
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METABOLITE -> PARENT |
FECAL
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
Other peaks (M2, M6A and M6B, M7, M12, M13, M24, and M25) represented <2% of the dose.
FECAL
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
Modest decreases in LDL and increases in HDL levels were observed, but trials were halted due to progression of coronary atherosclerosis and an increase in mortality.
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
|---|---|---|---|---|---|---|
| Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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| Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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