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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H19F8N5O2
Molecular Weight 489.3637
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GEMIGLIPTIN

SMILES

C1CC(CN(C[C@]([H])(CC(=O)N2CCc3c(C2)nc(C(F)(F)F)nc3C(F)(F)F)N)C1=O)(F)F

InChI

InChIKey=ZWPRRQZNBDYKLH-VIFPVBQESA-N
InChI=1S/C18H19F8N5O2/c19-16(20)3-1-12(32)31(8-16)6-9(27)5-13(33)30-4-2-10-11(7-30)28-15(18(24,25)26)29-14(10)17(21,22)23/h9H,1-8,27H2/t9-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H19F8N5O2
Molecular Weight 489.3637
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Gemigliptin, an orally active, CD26 antigen (dipeptidyl peptidase IV or DPP IV) antagonist, was developed by LG Life Sciences (Seoul, Korea) and was approved by the Ministry of Food and Drug safety in June 2012 for the treatment of Type 2 diabetes mellitus. Zemiglo is the brand name of gemigliptin. The company also signed licensing agreement with multinational pharmaceutical companies including Sanofi (Paris, France), and at present gemigliptin is approved in India, Columbia, Costa Rica, Panama, Ecuador and a few other countries. Registration studies are currently ongoing in several countries including Russia, Mexico and Thailand. Various studies have proven the efficacy and safety of gemigliptin for the treatment of T2DM, both as monotherapy as well as in combination with other anti-diabetic drugs. Gemigliptin binds to the S1, S2, and S2 extensive subsites of the DPP-4 enzyme. The piperidinone group of gemigliptin binds to the S1 subsite, where the upside F atom on the piperidin ring forms a hydrogen bond with the side chain of Tyr631 and the downside F atom makes a hydrophobic interaction with the side chain of Tyr666 and Tyr662. In addition, the key interaction occurs between the CF3 groups on the pyrimidino piperidine and the S2 extensive subsite of the DPP-4 substrate, which enhances the potency of the drug and increases its selectivity as well. Gemigliptin is a reversible and competitive inhibitor of DPP-4 enzyme with a Ki value of 7.25 ± 0.67 nM. It acts as a long-acting DPP-4 inhibitor which inhibits DPP-4 in a dose-dependent manner. In addition, it showed at least >23,000 fold selectivity for proteases such as DPP-8, DPP-9, and fibroblast activating protein – α. By preventing degradation of GLP-1 by DPP-4 inhibition, it increases insulin secretion, reduces glucagon secretion, decreases HbA1c, and prevents β-cell damage. Gemigliptin has also been investigated for the treatment of cancer and cisplatin adverse reaction.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Gemigliptin: An Update of Its Clinical Use in the Management of Type 2 Diabetes Mellitus.
2016 Oct
Gemigliptin: Newer Promising Gliptin for Type 2 Diabetes Mellitus.
2017 Nov-Dec
Patents

Sample Use Guides

The maximum daily recommended dose of Zemiglo (Gemigliptin) is 50 mg once daily. If a dose is missed, it should be taken as soon as the patient remembers. A double dose should not be taken on the same day.
Route of Administration: Oral
Gemigliptin showed the type of reversible and competitive DPP-4 inhibitor with a Ki value of 7.25±0.67 nM
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:25:45 UTC 2021
Edited
by admin
on Fri Jun 25 22:25:45 UTC 2021
Record UNII
5DHU18M5D6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GEMIGLIPTIN
INN   WHO-DD  
INN  
Official Name English
LC-150444
Code English
GEMIGLIPTIN [WHO-DD]
Common Name English
1-((2S)-2-AMINO-4-(2,4-BIS(TRIFLUOROMETHYL)-5,8-DIHYDROPYRIDO(3,4-D)PYRIMIDIN-7(6H)-YL)-4-OXOBUTYL)-5,5-DIFLUOROPIPERIDIN-2-ONE
Systematic Name English
PYRIDO(3,4-D)PYRIMIDINE, 7-((3S)-3-AMINO-4-(5,5-DIFLUORO-2-OXO-1-PIPERIDINYL)-1-OXOBUTYL)-5,6,7,8-TETRAHYDRO-2,4-BIS(TRIFLUOROMETHYL)-
Systematic Name English
GEMIGLIPTIN [INN]
Common Name English
LC15-0444
Code English
LC-15-0444
Code English
2-PIPERIDINONE, 1-((2S)-2-AMINO-4-(5,8-DIHYDRO-2,4-BIS(TRIFLUOROMETHYL)PYRIDO(3,4-D)PYRIMIDIN-7(6H)-YL)-4-OXOBUTYL)-5,5-DIFLUORO-
Systematic Name English
Classification Tree Code System Code
WHO-ATC A10BD18
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
WHO-VATC QA10BH06
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
WHO-ATC A10BH06
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
WHO-ATC A10BH52
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
NCI_THESAURUS C98086
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
Code System Code Type Description
DRUG CENTRAL
4833
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
CAS
911637-19-9
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL3707235
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
FDA UNII
5DHU18M5D6
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
NCI_THESAURUS
C118446
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
EVMPD
SUB180615
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
WIKIPEDIA
Gemigliptin
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
PUBCHEM
11953153
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
DRUG BANK
DB12412
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
INN
9291
Created by admin on Fri Jun 25 22:25:45 UTC 2021 , Edited by admin on Fri Jun 25 22:25:45 UTC 2021
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
FECAL
METABOLIC ENZYME -> SUBSTRATE
MAJOR
EXCRETED UNCHANGED
URINE
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
FECAL
METABOLITE -> PARENT
Six metabolites were detected, but only LC15-0636, the two times more potent active metabolite than gemigliptin
MAJOR
PLASMA
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC IN HEALTHY MALE SUBJECTS

ORAL ADMINISTRATION

SINGLE DOSE

Biological Half-life PHARMACOKINETIC IN HEALTHY MALE SUBJECTS

SINGLE DOSE

ORAL ADMINISTRATION