JTT-551

Details

Stereochemistry	ACHIRAL
Molecular Formula	C34H43N3O3S2
Molecular Weight	605.854
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCCC(CCC)C1=CC=C(OCC2=CC=C(C=C2)C3=CSC(CN(CC(O)=O)CC4=NC=C(S4)C(C)(C)C)=N3)C=C1

InChI

InChIKey=FKGBFRNVTCFMGU-UHFFFAOYSA-N

InChI=1S/C34H43N3O3S2/c1-6-8-25(9-7-2)26-14-16-28(17-15-26)40-22-24-10-12-27(13-11-24)29-23-41-32(36-29)20-37(21-33(38)39)19-31-35-18-30(42-31)34(3,4)5/h10-18,23,25H,6-9,19-22H2,1-5H3,(H,38,39)

HIDE SMILES / InChI

Molecular Formula	C34H43N3O3S2
Molecular Weight	605.854
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Substance Class	Chemical
Record UNII	VH3F3DR5X3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

JTT551

Preferred Name

English

JTT-551

Code

English

2-((5-TERT-BUTYLTHIAZOL-2-YL)METHYL-((4-(4-((4-(1-PROPYLBUTYL)PHENOXY)METHYL)PHENYL)THIAZOL-2-YL)METHYL)AMINO)ACETIC ACID

Systematic Name

English

GLYCINE, N-((5-(1,1-DIMETHYLETHYL)-2-THIAZOLYL)METHYL)-N-((4-(4-((4-(1-PROPYLBUTYL)PHENOXY)METHYL)PHENYL)-2-THIAZOLYL)METHYL)-

Systematic Name

English

N-((5-(1,1-DIMETHYLETHYL)-2-THIAZOLYL)METHYL)-N-((4-(4-((4-(1-PROPYLBUTYL)PHENOXY)METHYL)PHENYL)-2-THIAZOLYL)METHYL)GLYCINE

Systematic Name

English

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Code System

Code

Type

Description

FDA UNII

VH3F3DR5X3

PRIMARY

CAS

776309-04-7

PRIMARY

PUBCHEM

23080446

PRIMARY

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Related Record

Type

Details


					VH3F3DR5X3

JTT-551

ACTIVE MOIETY

Comments:

Class: Antihyperglycaemic; Mechanism of Action: Protein-tyrosine-phosphatase inhibitor; Highest Development Phase: Discontinued for Type 2 diabetes mellitus; Most Recent Events: 09 Aug 2007 Discontinued - Phase-I for Type-2 diabetes mellitus (PO),09 Aug 2007 Discontinued - Phase-I for Type-2 diabetes mellitus in Japan (PO), 31 Oct 2006 Phase-I clinical trials in Type-2 diabetes mellitus (PO)


					VH3F3DR5X3

JTT-551

ACTIVE MOIETY

Comments:

Protein tyrosine phosphatase 1B (PTP1B), a negative regulator of insulin signalling, is a novel therapeutic target for type 2 diabetes mellitus. JTT-551 showed an inhibitory effect on PTP1B with a Ki value of 0.22 microM, and a mixed-type inhibition mode. Ki values of TCPTP, CD45 and LAR were 9.3, 30 or higher and 30 or higher microM, respectively, and JTT-551 exhibited clear selectivity against the other PTPs. Moreover, JTT-551 increased the insulin-stimulated glucose uptake in L6 cells. A single administration of JTT-551 in ob/ob mice enhanced the IR phosphorylation of liver and reduced the glucose level. In db/db mice, chronic administration showed a hypoglycaemic effect without an acceleration of body weight gain. JTT-551, a newly developed PTP1B inhibitor, improves glucose metabolism by enhancement of insulin signalling and could be useful in the treatment of type 2 diabetes mellitus.


					VH3F3DR5X3

JTT-551

ACTIVE MOIETY

Comments:

Protein tyrosine phosphatase 1B (PTP1B) is a negative regulator of leptin signaling as well as insulin signaling. JTT-551 is a new PTP1B inhibitor, which is reported to improve glucose metabolism by enhancement of insulin signaling. We have evaluated an antiobesity effect of JTT-551 using diet-induced obesity (DIO) mice. A single administration of JTT-551 was provided to DIO mice with or without leptin, and DIO mice were given food containing JTT-551 for six weeks. A single administration of JTT-551 with leptin treatment enhanced the food inhibition and the signal transducer and activator of transcription 3 (STAT3) phosphorylation in hypothalamus. Moreover, chronic administration of JTT-551 showed an antiobesity effect and an improvement of glucose and lipid metabolism in DIO mice.

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