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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H13N5
Molecular Weight 155.2012
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMEGLIMIN

SMILES

C[C@]1([H])NC(=N)NC(=N1)N(C)C

InChI

InChIKey=GFICWFZTBXUVIG-SCSAIBSYSA-N
InChI=1S/C6H13N5/c1-4-8-5(7)10-6(9-4)11(2)3/h4H,1-3H3,(H3,7,8,9,10)/t4-/m1/s1

HIDE SMILES / InChI

Molecular Formula C6H13N5
Molecular Weight 155.2012
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Imeglimin is the first in class tetrahydrotriazine‐containing oral glucose-lowering agent that has been studied in clinical trials as a possible monotherapy or add-on therapy to lower fasting plasma glucose. It is being developed as an alternative and a complement to drugs that act on insulin‐resistant organs or drugs acting on insulin secretion and β‐cell protection. When investigated in preclinical studies, Imeglimin showed that it can target insulin‐resistant organs by decreasing excessive hepatic glucose production and increasing muscle glucose uptake. It also showed a potential to restore appropriate glucose‐stimulated insulin secretion and protect β‐cells from cell death under high glucose conditions. Imeglimin acts on the liver, muscle, and the pancreas (6), three key organs involved in the pathophysiology of type 2 diabetes through suspected mechanisms targeting the mitochondria and reduced oxidative stress. Imeglimin decreases hepatic glucose production and increases muscle glucose uptake. Recently, Imeglimin demonstrated increased insulin secretion in response to glucose in diabetic patients during a hyperglycemic clamp study. In clinical trials, Imeglimin treatment for 7 days raised the insulin secretory response to glucose, improved β-cell glucose sensitivity and tended to decrease hepatic insulin extraction. Imeglimin did not affect glucagon secretion.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Imeglimin: A Potential New Multi-Target Drug for Type 2 Diabetes.
2015 Sep
Patents

Patents

Sample Use Guides

1500 mg or placebo twice daily for 7 days
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:50:43 UTC 2021
Edited
by admin
on Sat Jun 26 12:50:43 UTC 2021
Record UNII
UU226QGU97
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IMEGLIMIN
INN   WHO-DD  
INN  
Official Name English
IMEGLIMIN [INN]
Common Name English
(4R)-6-(DIMETHYLAMINO)-4-METHYL-4,5-DIHYDRO-1,3,5-TRIAZIN-2-AMINE
Systematic Name English
IMEGLIMIN [WHO-DD]
Common Name English
EMD-387008
Code English
Classification Tree Code System Code
NCI_THESAURUS C29711
Created by admin on Sat Jun 26 12:50:43 UTC 2021 , Edited by admin on Sat Jun 26 12:50:43 UTC 2021
Code System Code Type Description
PUBCHEM
24812808
Created by admin on Sat Jun 26 12:50:43 UTC 2021 , Edited by admin on Sat Jun 26 12:50:43 UTC 2021
PRIMARY
INN
8969
Created by admin on Sat Jun 26 12:50:43 UTC 2021 , Edited by admin on Sat Jun 26 12:50:43 UTC 2021
PRIMARY
EPA CompTox
775351-65-0
Created by admin on Sat Jun 26 12:50:43 UTC 2021 , Edited by admin on Sat Jun 26 12:50:43 UTC 2021
PRIMARY
FDA UNII
UU226QGU97
Created by admin on Sat Jun 26 12:50:43 UTC 2021 , Edited by admin on Sat Jun 26 12:50:43 UTC 2021
PRIMARY
CAS
775351-65-0
Created by admin on Sat Jun 26 12:50:43 UTC 2021 , Edited by admin on Sat Jun 26 12:50:43 UTC 2021
PRIMARY
DRUG BANK
DB12509
Created by admin on Sat Jun 26 12:50:43 UTC 2021 , Edited by admin on Sat Jun 26 12:50:43 UTC 2021
PRIMARY
NCI_THESAURUS
C132841
Created by admin on Sat Jun 26 12:50:43 UTC 2021 , Edited by admin on Sat Jun 26 12:50:43 UTC 2021
PRIMARY
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Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC SINGLE ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC SINGLE ORAL ADMINISTRATION