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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C19H24NO3.Ca
Molecular Weight 668.876
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MITIGLINIDE CALCIUM ANHYDROUS

SMILES

[Ca++].[H][C@@]12CN(C[C@]1([H])CCCC2)C(=O)C[C@H](CC3=CC=CC=C3)C([O-])=O.[H][C@@]45CN(C[C@]4([H])CCCC5)C(=O)C[C@H](CC6=CC=CC=C6)C([O-])=O

InChI

InChIKey=PMRVFZXOCRHXFE-FMEJWYFOSA-L
InChI=1S/2C19H25NO3.Ca/c2*21-18(20-12-15-8-4-5-9-16(15)13-20)11-17(19(22)23)10-14-6-2-1-3-7-14;/h2*1-3,6-7,15-17H,4-5,8-13H2,(H,22,23);/q;;+2/p-2/t2*15-,16+,17-;/m00./s1

HIDE SMILES / InChI
Molecular Formula C19H24NO3
Molecular Weight 314.3988
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula Ca
Molecular Weight 40.078
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Mitiglinide is a drug for the treatment of type 2 diabetes currently marked under tradename Glufast. Glufast® is available as the tablet for oral use, containing 5 mg or 10 mg of Mitiglinide calcium hydrate. The recommended dose is 10 mg three times daily just before each meal (within 5 minutes). Mitiglinide was approved by Pharmaceuticals and Medical Devices Agency of Japan (PMDA) on January 29, 2004, and is currently co-marketed in Japan by Kissei and Takeda. Mitiglinide is a rapid-acting insulin secretion-stimulating agent, its belongs to the meglitinide (glinide) class of blood glucose-lowering drugs. Mitiglinide is thought to stimulate insulin secretion by closing the ATP-sensitive K(+) (K(ATP)) channels in pancreatic beta-cells.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 4.0 nM [IC50]
Inhibitor
8297
 3.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Glufast

Approved Use

Unknown

Launch Date

1.07524797E12
PubMed

PubMed

TitleDatePubMed
Effects of mitiglinide (S 21403) on Kir6.2/SUR1, Kir6.2/SUR2A and Kir6.2/SUR2B types of ATP-sensitive potassium channel.
2001 Apr
Absence of exacerbation of myocardial stunning in anesthetized dogs treated with KAD-1229, a novel hypoglycemic agent.
2001 Nov 23
Effect of KAD-1229, a novel hypoglycaemic agent, on plasma glucose levels after meal load in type 2 diabetic rats.
2002 May-Jun
[Mitiglinide (KAD-1229)].
2002 Sep
[Nateglinide and mitiglinide].
2003 Jul
[Achieving better control of blood sugar--understanding of oral hypoglycemic agents according to their characteristics in pharmacological action mechanism (discussion)].
2004 Apr
The impact of ATP-sensitive K+ channel subtype selectivity of insulin secretagogues for the coronary vasculature and the myocardium.
2004 Dec
Characterization of the action of S 21403 (mitiglinide) on insulin secretion and biosynthesis in normal and diabetic beta-cells.
2005 Nov
Determination of mitiglinide in rat plasma by high-performance liquid chromatography with UV detection.
2006 Apr 13
[Glinide(s), sulfonylurea(s)].
2006 Nov
Imaging docking and fusion of insulin granules induced by antidiabetes agents: sulfonylurea and glinide drugs preferentially mediate the fusion of newcomer, but not previously docked, insulin granules.
2006 Oct
Long-term effect of combination therapy with mitiglinide and once daily insulin glargine in patients who were successfully switched from intensive insulin therapy in short-term study.
2007 Feb
High-performance liquid chromatography-electrospray ionization mass spectrometry determination of mitiglinide in human plasma and its pharmacokinetics.
2007 Feb
Nateglinide and mitiglinide, but not sulfonylureas, induce insulin secretion through a mechanism mediated by calcium release from endoplasmic reticulum.
2007 Jul
Insulin-releasing activity of a series of phenylalanine derivatives.
2008 Sep
[Design, synthesis and hypoglycemic activity of alpha-benzylsuccinic acid derivatives].
2009 May
Multicentre, double-blind, randomized study of mitiglinide compared with nateglinide in type 2 diabetes mellitus patients in China.
2009 May-Jun
Mitiglinide: a novel agent for the treatment of type 2 diabetes mellitus.
2010 Oct
A prospective, randomized, multicenter trial comparing the efficacy and safety of the concurrent use of long-acting insulin with mitiglinide or voglibose in patients with type 2 diabetes.
2015
Patents

Patents

CN106188077
3
WO201615394
3

Sample Use Guides

In Vivo Use Guide
Curator's Comment: https://clinicaltrials.gov/ct2/show/NCT02143765
The recommended dose is 10 mg three times daily just before each meal (within 5 minutes).
Route of Administration: Oral
In Vitro Use Guide
3T3-L1 cells were challenged during the first 4 days of differentiation with Mitiglinide at 1, 10 and 100 mkM. Seven days after the induction of 3T3-L1 cells, oil red O staining was used to detect triglyceride accumulation in 3T3-L1 cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:01:10 UTC 2023
Edited
by admin
on Sat Dec 16 05:01:10 UTC 2023
Record UNII
P5WOR98G68
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MITIGLINIDE CALCIUM ANHYDROUS
Common Name English
2H-ISOINDOLE-2-BUTANOIC ACID, OCTAHYDRO-.GAMMA.-OXO-.ALPHA.-(PHENYLMETHYL)-, CALCIUM SALT (2:1), (.ALPHA.S,3AR,7AS)-
Common Name English
MITIGLINIDE CALCIUM
WHO-DD  
Common Name English
MITIGLINIDE CALCIUM SALT ANHYDROUS [MI]
Common Name English
MITIGLINIDE CALCIUM SALT ANHYDROUS
MI  
Common Name English
(S)-2-BENZYL-4-OXO-4-(CIS-PERHYDROISOINDOL-2-YL)BUTYRIC ACID CALCIUM SALT
Common Name English
Mitiglinide calcium [WHO-DD]
Common Name English
ANHYDROUS MITIGLINIDE CALCIUM
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C98079
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C132050
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
EVMPD
SUB25644
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
PUBCHEM
5478927
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
MERCK INDEX
m7566
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
FDA UNII
P5WOR98G68
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
EVMPD
SUB25643
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
SMS_ID
100000091418
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
CAS
145525-41-3
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
EPA CompTox
DTXSID90872410
Created by admin on Sat Dec 16 05:01:11 UTC 2023 , Edited by admin on Sat Dec 16 05:01:11 UTC 2023
PRIMARY
Related Record Type Details
Structure of MITIGLINIDE CALCIUM DIHYDRATE
SOLVATE->ANHYDROUS
Structure of MITIGLINIDE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of MITIGLINIDE
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