5-[(2,4-Dioxo-5-thiazolidinyl)methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide

Investigational

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H17F3N2O4S
Molecular Weight	438.42
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 5-[(2,4-Dioxo-5-thiazolidinyl)methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide

Structure Search

SMILES

COC1=C(C=C(CC2SC(=O)NC2=O)C=C1)C(=O)NCC3=CC=C(C=C3)C(F)(F)F

InChI

InChIKey=NFFXEUUOMTXWCX-UHFFFAOYSA-N

InChI=1S/C20H17F3N2O4S/c1-29-15-7-4-12(9-16-18(27)25-19(28)30-16)8-14(15)17(26)24-10-11-2-5-13(6-3-11)20(21,22)23/h2-8,16H,9-10H2,1H3,(H,24,26)(H,25,27,28)

HIDE SMILES / InChI

Molecular Formula	C20H17F3N2O4S
Molecular Weight	438.42
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17322144 | https://www.ncbi.nlm.nih.gov/pubmed/16772365 | https://www.ncbi.nlm.nih.gov/pubmed/16542056

MK-0767 is a potent hypoglycaemic insulin sensitizer being evaluated by Kyorin with potential as an antidiabetic agent. MK-0767 acts as a dual agonist of the peroxisome proliferator-activated receptors alpha and gamma, induced high-affinity interactions of PPARα and PPARγ with the transcriptional coactivator CBP in vitro. In ob/ob mice, MK-0767 normalized hyperglycemia and hyperinsulinemia with equal or greater potency and efficacy than pioglitazone. Treatment of hamsters with MK-0767 produced substantial reductions in blood cholesterol and triglycerides. In dogs, MK-0767 reduced serum cholesterol levels with a potency more than 10-fold greater than simvastatin. The efficacies of MK-0767 and simvastatin were additive when given together.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor gamma 118 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10691680	Agonist 2752		83.0 nM [EC50]
Peroxisome proliferator-activated receptor gamma 118 Target ID: CHEMBL2459 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10691680	Agonist 2752		140.0 nM [EC50]

C_max

Value	Dose	Analyte	Population
109.2 μg/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
40.5 μg/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
50 μg/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
89.8 μg/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
247.5 μg/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
125.6 μg/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
402 ng/mL EXPERIMENT https://dmd.aspetjournals.org/content/34/9/1457	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
8.82 μg × h/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.59 μg × h/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.5 μg × h/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.36 μg × h/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11 μg × h/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.24 μg × h/mL EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
14.5 μg × h/mL EXPERIMENT https://dmd.aspetjournals.org/content/34/9/1457	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
35.6 h EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
36.6 h EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
33.5 h EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
32.6 h EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
29.9 h EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
30.7 h EXPERIMENT https://accp1.onlinelibrary.wiley.com/doi/epdf/10.1177/0091270006297141	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
32 h EXPERIMENT https://dmd.aspetjournals.org/content/34/9/1457	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	MK-0767 plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

PubMed

Title	Date	PubMed
MK-0767, a novel dual PPARalpha/gamma agonist, displays robust antihyperglycemic and hypolipidemic activities.	2004-05-28	15120604
Combination therapy with PPARgamma and PPARalpha agonists increases glucose-stimulated insulin secretion in db/db mice.	2003-05	12676649
MK-767. Kyorin/Banyu/Merck.	2003-04	12808885
[KRP-297, MCC-555].	2001-11	11712408
Fatty-acyl-CoA thioesters inhibit recruitment of steroid receptor co-activator 1 to alpha and gamma isoforms of peroxisome-proliferator-activated receptors by competing with agonists.	2001-01-15	11139385
Fenofibrate and rosiglitazone lower serum triglycerides with opposing effects on body weight.	2000-05-10	10799317
Amelioration by KRP-297, a new thiazolidinedione, of impaired glucose uptake in skeletal muscle from obese insulin-resistant animals.	1999-11	10582556
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.	1999-07-14	10403814
(3-substituted benzyl)thiazolidine-2,4-diones as structurally new antihyperglycemic agents.	1999-02-22	10098657
A novel insulin sensitizer acts as a coligand for peroxisome proliferator-activated receptor-alpha (PPAR-alpha) and PPAR-gamma: effect of PPAR-alpha activation on abnormal lipid metabolism in liver of Zucker fatty rats.	1998-12	9836514

Patents

Sample Use Guides

In Vivo Use Guide

0.3-25 mg of MK-0767 were administered once daily for 14 days.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:25:15 GMT 2025` Edited by `admin` on `Wed Apr 02 07:25:15 GMT 2025`
Record UNII	2CP9XG3TH2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MK-767

Preferred Name

English

5-[(2,4-Dioxo-5-thiazolidinyl)methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide

Systematic Name

English

Benzamide, 5-[(2,4-dioxo-5-thiazolidinyl)methyl]-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]-

Systematic Name

English

(±)-5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[(4-trifluoromethyl)phenyl]methyl]benzamide

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID90870239

Created by admin on Wed Apr 02 07:25:15 GMT 2025 , Edited by admin on Wed Apr 02 07:25:15 GMT 2025

PRIMARY

FDA UNII

2CP9XG3TH2

Created by admin on Wed Apr 02 07:25:15 GMT 2025 , Edited by admin on Wed Apr 02 07:25:15 GMT 2025

PRIMARY

PUBCHEM

151183

Created by admin on Wed Apr 02 07:25:15 GMT 2025 , Edited by admin on Wed Apr 02 07:25:15 GMT 2025

PRIMARY

CAS

213252-19-8

Created by admin on Wed Apr 02 07:25:15 GMT 2025 , Edited by admin on Wed Apr 02 07:25:15 GMT 2025

PRIMARY

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Amount:

Name	Property Type	Parameters
Tmax	PHARMACOKINETIC	ORAL ADMINISTRATION

Biological Half-life	PHARMACOKINETIC	ORAL ADMINISTRATION

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17322144 | https://www.ncbi.nlm.nih.gov/pubmed/16772365 | https://www.ncbi.nlm.nih.gov/pubmed/16542056

Approval Year

Targets

Cmax

AUC

T1/2

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17322144 | https://www.ncbi.nlm.nih.gov/pubmed/16772365 | https://www.ncbi.nlm.nih.gov/pubmed/16542056

C_max

T_1/2