TORCETRAPIB

Investigational

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

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Description

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
Cholesteryl ester transfer protein 15	Inhibitor 8,504		25.2 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Hyperlipidemia 82	Primary	Phase III 665	Unknown
Hypercholesterolemia 51	Primary	Phase III 665	Unknown
Coronary heart disease 43	Primary	Phase III 665	Unknown
Fredrickson type IV hypertriglyceridemia 1	Primary	Phase III 665	Unknown
Fredrickson type III hyperlipoproteinemia 1	Primary	Phase III 665	Unknown

C_max

Value	Dose	Analyte	Population
373 nM	60 mg 1 times / day multiple, oral	TORCETRAPIB plasma	Homo sapiens
527 ng/mL	120 mg single, oral	TORCETRAPIB plasma	Homo sapiens
576 ng/mL	120 mg single, oral	TORCETRAPIB plasma	Homo sapiens
2920 ng/mL	120 mg single, oral	BISTRIFLUOROMETHYLBENZOIC ACID plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
3670 nM × h	60 mg 1 times / day multiple, oral	TORCETRAPIB plasma	Homo sapiens
5040 ng × h/mL	120 mg single, oral	TORCETRAPIB plasma	Homo sapiens
7570 ng × h/mL	120 mg single, oral	TORCETRAPIB plasma	Homo sapiens
452000 ng × h/mL	120 mg single, oral	BISTRIFLUOROMETHYLBENZOIC ACID plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.4 h	60 mg 1 times / day multiple, oral	TORCETRAPIB plasma	Homo sapiens
9.1 h	120 mg single, oral	TORCETRAPIB plasma	Homo sapiens
201 h	120 mg single, oral	TORCETRAPIB plasma	Homo sapiens
211 h	120 mg single, oral	TORCETRAPIB plasma	Homo sapiens
117 h	120 mg single, oral	BISTRIFLUOROMETHYLBENZOIC ACID plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 substrate 1,946	substrate 1,193 inhibitor 2,438	inhibitor 2,507 substrate 1,388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2A6 626 CYP2B6 776 CYP2C8 810 P-gp 2,052 CYP3A5 446 CYP2C19 1,119 CYP1A1 389 CYP1A2 1,197 CYP2E1 729 CYP1B1 104 CYP4A11 137	CYP11B2 1

Drug as perpetrator

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Target	Modality	Activity
CYP2C9 2,497	inhibitor 4,027	no
CYP2D6 2,546	inhibitor 4,027	no
CYP3A4 2,633	inhibitor 4,027	yes [IC50 1.6933 uM]
CYP11B2 12	inducer 1,966	yes

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Drug as victim

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Target	Modality	Activity
CYP1A1 389	substrate 4,014	no
CYP1A2 1,197	substrate 4,014	no
CYP1B1 104	substrate 4,014	no
CYP2A6 626	substrate 4,014	no
CYP2B6 776	substrate 4,014	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY105534	https://www.001chemical.com/chem/search?q=DY105534
1PlusChem LLC	1P002SUI	https://www.1pchem.com/search?query=1P002SUI
A2B Chem	AB29898	http://a2bchem.com/prod/AB29898
Aceschem	ACF022979	https://www.aceschem.com/catalog/search.do?q=ACF022979
AK Scientific	Y0216	https://aksci.com/item_detail.php?cat=Y0216

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PubMed

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Title	Date	PubMed
Gateways to clinical trials.	2004 Dec	15672123
Increasing high-density lipoprotein cholesterol through cholesteryl Ester transfer protein inhibition: a next step in the fight against cardiovascular disease?	2005 Dec	16503868
Raising high-density lipoprotein with cholesteryl ester transfer protein inhibitors.	2006 Apr	16487747
Targeting cholesteryl ester transfer protein for the prevention and management of cardiovascular disease.	2006 Feb 7	16458126
Therapeutic elevation of HDL-cholesterol to prevent atherosclerosis and coronary heart disease.	2006 Sep	16574234

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Patents

Sample Use Guides

In Vivo Use Guide

Patients were receiving torcetrapib at a dose 10, 30, 60, or 90 mg/day.

Route of Administration: Oral

In Vitro Use Guide

For determination of in vitro potency, a pool of plasma from 3 individuals having a CETP concentration 1.95 ug/mL (37 nM) was tested and treated with 10-1000 nM of torcetrapib.

Show entries

Name

Type

Language

CP-529,414

Preferred Name

English

TORCETRAPIB

Official Name

English

torcetrapib [INN]

Common Name

English

Torcetrapib [WHO-DD]

Common Name

English

CP-529414

Code

English

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Classification Tree

Code System

Code

Agent Affecting Digestive System or Metabolism

NCI_THESAURUS

C29703

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Code System

Code

Type

Description

CAS

262352-17-0

PRIMARY

WIKIPEDIA

TORCETRAPIB

PRIMARY

USAN

NN-58

PRIMARY

EPA CompTox

DTXSID20180873

PRIMARY

FDA UNII

4N4457MV2U

PRIMARY

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ACTIVE MOIETY


					4N4457MV2U

TORCETRAPIB

METABOLITE (PARENT)


					QD76GO5OT6

DE(ETHOXYCARBONYL)-2-HYDROXYETHOXYCARBONYL-TORCETRAPIB

METABOLITE (PARENT)


					51Y529EB2B

2-(6-(TRIFLUOROMETHYL)QUINOLIN-2-YL)ETHANOL

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator