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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H24N6O
Molecular Weight 328.4121
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of K-579

SMILES

CC1(CCN(CC1)C2=NC=CC=N2)NCC(=O)N3CCC[C@H]3C#N

InChI

InChIKey=JERPHRNGJBSFAP-AWEZNQCLSA-N
InChI=1S/C17H24N6O/c1-17(21-13-15(24)23-9-2-4-14(23)12-18)5-10-22(11-6-17)16-19-7-3-8-20-16/h3,7-8,14,21H,2,4-6,9-11,13H2,1H3/t14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H24N6O
Molecular Weight 328.4121
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15556158 | https://www.ncbi.nlm.nih.gov/pubmed/26101059 | https://www.ncbi.nlm.nih.gov/pubmed/26101059

K-579 ((S)-1-[4-methyl-1-(2-pyrimidinyl)-4-piperidylamino]acetyl-2-pyrrolidinecarbonitrile) is potent and slower binding dipeptidyl peptidase IV inhibitor which was investigated as an antidiabetic drug. K579 suppressed the blood glucose elevation after an oral glucose tolerance test with the increment of plasma insulin and active forms of Glucagon-like peptide-1 (GLP-1). During repetitive glucose loading using Zucker fatty rats, pretreatment with K579 attenuated the glucose excursion after the second glucose loading as well as the first glucose loading without inducing hypoglycemia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Nerve growth factor induces endothelial cell invasion and cord formation by promoting matrix metalloproteinase-2 expression through the phosphatidylinositol 3-kinase/Akt signaling pathway and AP-2 transcription factor.
2007 Oct 19
Patents

Sample Use Guides

Zucker fatty rats was treatment with K579 at a doses 0.1, 0.3 or 1mg/kg
Route of Administration: Oral
GLUTag cells were seeded onto poly-D lysine coated 96 well plates at 8000 cells/well and grown for approximately 48 h. Cells were incubated in assay buffer containing test ligand for1 h at 37 °C. Cells were then washed by four exchanges of fresh buffer, before exposure to buffer containing the diepetidyl peptidase IV inhibitor K-579(100nM)7test compoundfor2hat37 °C. Supernatant was then removed and GLP-1 concentration measured by the 1 concentration measured by the Millipore ELISA kit, as per the manufacturers instructions. Fluorescencewas measured at abs/emof355/460nm using a TecanSafire, and samples compared to a standard curve.
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:59:48 GMT 2023
Edited
by admin
on Sat Dec 16 07:59:48 GMT 2023
Record UNII
74P4VV90RU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
K-579
Common Name English
2-PYRROLIDINECARBONITRILE, 1-(2-((4-METHYL-1-(2-PYRIMIDINYL)-4-PIPERIDINYL)AMINO)ACETYL)-, (2S)-
Systematic Name English
2-PYRROLIDINECARBONITRILE, 1-(((4-METHYL-1-(2-PYRIMIDINYL)-4-PIPERIDINYL)AMINO)ACETYL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
9818824
Created by admin on Sat Dec 16 07:59:48 GMT 2023 , Edited by admin on Sat Dec 16 07:59:48 GMT 2023
PRIMARY
CAS
440100-64-1
Created by admin on Sat Dec 16 07:59:48 GMT 2023 , Edited by admin on Sat Dec 16 07:59:48 GMT 2023
PRIMARY
FDA UNII
74P4VV90RU
Created by admin on Sat Dec 16 07:59:48 GMT 2023 , Edited by admin on Sat Dec 16 07:59:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID10431306
Created by admin on Sat Dec 16 07:59:48 GMT 2023 , Edited by admin on Sat Dec 16 07:59:48 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY