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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

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

2004
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
Effect of KAD-1229, a nonsulfonylurea hypoglycemic agent, on plasma glucose and insulin in streptozotocin-induced diabetic dogs.
2001 Feb
Absence of exacerbation of myocardial stunning in anesthetized dogs treated with KAD-1229, a novel hypoglycemic agent.
2001 Nov 23
The effects of mitiglinide (KAD-1229), a new anti-diabetic drug, on ATP-sensitive K+ channels and insulin secretion: comparison with the sulfonylureas and nateglinide.
2001 Nov 9
Pharmacology of the meglitinide analogs: new treatment options for type 2 diabetes mellitus.
2003
[Nateglinide and mitiglinide].
2003 Jul
Mitiglinide: KAD 1229, S 21403.
2004
[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
[Pharmacological and clinical profile of mitiglinide calcium hydrate (Glufast), a new insulinotropic agent with rapid onset].
2004 Oct
[Significance of insulin secretion pattern lectured by "glinides" in the treatment of postprandial hyperglycemia].
2005 Dec
[Effects of mitiglinide in treatment of impaired glucose tolerance].
2005 Feb
[Selection of oral antidiabetic drugs].
2005 Feb
Characterization of the action of S 21403 (mitiglinide) on insulin secretion and biosynthesis in normal and diabetic beta-cells.
2005 Nov
Effects of S21403 (mitiglinide) on postprandial generation of oxidative stress and inflammation in type 2 diabetic patients.
2005 Sep
Effects of mitiglinide on glucose-induced insulin release into the portal vein and fat-induced triglyceride elevation in prediabetic and diabetic OLETF rats.
2006 Apr
Effects of mitiglinide and sulfonylureas in isolated canine coronary arteries and perfused rat hearts.
2006 Feb 15
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
High-performance liquid chromatography-electrospray ionization mass spectrometry determination of mitiglinide in human plasma and its pharmacokinetics.
2007 Feb
Insulin-releasing activity of a series of phenylalanine derivatives.
2008 Sep
Postprandial hyperglycemia as an etiological factor in vascular failure.
2009 Apr 29
Ca(2+) channels on the move.
2009 Dec 29
Pleiotropic effects of mitiglinide in type 2 diabetes mellitus.
2009 Nov-Dec
Efficacy and safety of mitiglinide in diabetic patients on maintenance hemodialysis.
2010
Combination therapy with mitiglinide and voglibose improves glycemic control in type 2 diabetic patients on hemodialysis.
2010 Feb
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.
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 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C132050
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
EVMPD
SUB25644
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
PUBCHEM
5478927
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
MERCK INDEX
m7566
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
FDA UNII
P5WOR98G68
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
EVMPD
SUB25643
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
SMS_ID
100000091418
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
CAS
145525-41-3
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID90872410
Created by admin on Sat Dec 16 05:01:11 GMT 2023 , Edited by admin on Sat Dec 16 05:01:11 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of MITIGLINIDE
NIH
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