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Details

Stereochemistry ACHIRAL
Molecular Formula C22H30N2O2
Molecular Weight 354.4858
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TAK-100

SMILES

CCC1=NC(CC(C)(C)C)=C(CN)C(C2=CC=C(C)C=C2)=C1CC(O)=O

InChI

InChIKey=HQVOROHHYWZJLD-UHFFFAOYSA-N
InChI=1S/C22H30N2O2/c1-6-18-16(11-20(25)26)21(15-9-7-14(2)8-10-15)17(13-23)19(24-18)12-22(3,4)5/h7-10H,6,11-13,23H2,1-5H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula C22H30N2O2
Molecular Weight 354.4858
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Discovery of a 3-pyridylacetic acid derivative (TAK-100) as a potent, selective and orally active dipeptidyl peptidase IV (DPP-4) inhibitor.
2011 Feb 10
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:46:03 GMT 2023
Edited
by admin
on Sat Dec 16 11:46:03 GMT 2023
Record UNII
6TEM3HH2EG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TAK-100
Common Name English
2-(5-(AMINOMETHYL)-6-(2,2-DIMETHYLPROPYL)-2-ETHYL-4-(P-TOLYL)-3-PYRIDYL)ACETIC ACID
Systematic Name English
5-(AMINOMETHYL)-6-(2,2-DIMETHYLPROPYL)-2-ETHYL-4-(4-METHYLPHENYL)-3-PYRIDINEACETIC ACID
Common Name English
3-PYRIDINEACETIC ACID, 5-(AMINOMETHYL)-6-(2,2-DIMETHYLPROPYL)-2-ETHYL-4-(4-METHYLPHENYL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
11996845
Created by admin on Sat Dec 16 11:46:03 GMT 2023 , Edited by admin on Sat Dec 16 11:46:03 GMT 2023
PRIMARY
FDA UNII
6TEM3HH2EG
Created by admin on Sat Dec 16 11:46:03 GMT 2023 , Edited by admin on Sat Dec 16 11:46:03 GMT 2023
PRIMARY
CAS
907609-33-0
Created by admin on Sat Dec 16 11:46:03 GMT 2023 , Edited by admin on Sat Dec 16 11:46:03 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY
Inhibition of dipeptidyl peptidase IV (DPP-4) is an exciting new approach for the treatment of diabetes. After further optimization, we identified a hydrate of (5-(aminomethyl)-6-(2,2-dimethylpropyl)-2-ethyl-4-(4-methylphenyl)pyridin-3-yl)acetic acid (30c) as a potent and selective DPP-4 inhibitor. The desired interactions with the critical active-site residues, such as a salt-bridge interaction with Arg125, were confirmed by X-ray cocrystal structure analysis. In addition, compound 30c showed a desired preclinical safety profile, and it was encoded as TAK-100. 30c (TAK-100) Data for inhibition of dipeptidyl peptidase IV (DPP-4): IC50-PP-4a = 5.3(5.1-5.4)nM, IC50-DPP-2b = >100000nM, IC50-DPP-8c = >100000nM, IC50-DPP-9d = 60000(48000-79000)nM
ACTIVE MOIETY
Originator: Takeda; Class: Antihyperglycaemic; Mechanism of Action: CD26 antigen inhibitor; Highest Development Phase: Discontinued for Type 2 diabetes mellitus; Most Recent Events: 21 May 2010 Discontinued - Phase-I for Type-2 diabetes mellitus in Japan (PO), 06 May 2010 TAK 100 is still in phase I trials for Type-2 diabetes in Japan, 31 Jan 2008 Phase-I clinical trials in Type-2 diabetes mellitus in Japan (PO)