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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
Rapid acting insulinotropic agents: restoration of early insulin secretion as a physiologic approach to improve glucose control.
2001 Sep
Study of the insulinotropic effect of the novel antihyperglycemic agent KAD-1229 using HIT T15 cells, a hamster's insulinoma cell line.
2002
Effect of KAD-1229, a novel hypoglycaemic agent, on plasma glucose levels after meal load in type 2 diabetic rats.
2002 May-Jun
[Nateglinide and mitiglinide].
2003 Jul
[Pharmacological and clinical profile of mitiglinide calcium hydrate (Glufast), a new insulinotropic agent with rapid onset].
2004 Oct
Characterization of the action of S 21403 (mitiglinide) on insulin secretion and biosynthesis in normal and diabetic beta-cells.
2005 Nov
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
Therapeutic efficacy of mitiglinide combined with once daily insulin glargine after switching from multiple daily insulin regimen of aspart insulin and glargine in patients with type 2 diabetes mellitus.
2006 Feb
[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
Effect of combination therapy of a rapid-acting insulin secretagogue (glinide) with premixed insulin in type 2 diabetes mellitus.
2007
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
Carboxyl-glucuronidation of mitiglinide by human UDP-glucuronosyltransferases.
2007 Jun 1
Mitiglinide, a novel oral hypoglycemic agent, preserves the cardioprotective effect of ischemic preconditioning in isolated perfused rat hearts.
2007 May
Miglitol increases the adiponectin level and decreases urinary albumin excretion in patients with type 2 diabetes mellitus.
2007 Nov
Liquid chromatography/electrospray ionization tandem mass spectrometry for the quantification of mitiglinide in human plasma: validation and its application to pharmacokinetic studies.
2008 Aug
Quantitative determination of mitiglinide in human plasma by ultra-performance liquid chromatography/electrospray ionization tandem mass spectrometry.
2008 Jun 1
Mitiglinide: a rapid- and short-acting non-sulfonylurea insulinotropic agent for the treatment of type 2 diabetic patients.
2008 Oct
Insulin-releasing activity of a series of phenylalanine derivatives.
2008 Sep
Glinide, but not sulfonylurea, can evoke insulin exocytosis by repetitive stimulation: imaging analysis of insulin exocytosis by secretagogue-induced repetitive stimulations.
2009
Effect of mitiglinide on glycemic control over 52 weeks in Japanese type 2 diabetic patients insufficiently controlled with pioglitazone monotherapy.
2009
Addition of mitiglinide to pioglitazone monotherapy improves overall glycemic control in Japanese patients with type 2 diabetes: a randomized double blind trial.
2009
Postprandial hyperglycemia as an etiological factor in vascular failure.
2009 Apr 29
Ca(2+) channels on the move.
2009 Dec 29
Effect of insulin-unstimulated diabetic therapy with miglitol on serum cystatin C level and its clinical significance.
2009 Jan
Treatment with glimepiride, but not mitiglinide and short-acting insulin, resists body weight and abdominal fat reduction under dietary energy restriction.
2009 Mar
[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
Effect of mitiglinide on Streptozotocin-induced experimental type 2 diabetic rats: a urinary metabonomics study based on ultra-performance liquid chromatography-tandem mass spectrometry.
2009 Nov 1
Pleiotropic effects of mitiglinide in type 2 diabetes mellitus.
2009 Nov-Dec
Design of nateglinide controlled release tablet containing erosion matrix tablet and multiple administration study in normal beagle dogs.
2009 Sep
Efficacy and safety of mitiglinide in diabetic patients on maintenance hemodialysis.
2010
Nateglinide controlled release tablet containing compressionable enteric coated granules.
2010 Sep
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
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