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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H25NO3
Molecular Weight 315.4074
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MITIGLINIDE

SMILES

c1ccc(cc1)C[C@@]([H])(CC(=O)N2C[C@]3([H])CCCC[C@]3([H])C2)C(=O)O

InChI

InChIKey=WPGGHFDDFPHPOB-BBWFWOEESA-N
InChI=1S/C19H25NO3/c21-18(20-12-15-8-4-5-9-16(15)13-20)11-17(19(22)23)10-14-6-2-1-3-7-14/h1-3,6-7,15-17H,4-5,8-13H2,(H,22,23)/t15-,16+,17-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H25NO3
Molecular Weight 315.4074
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Insulinotropic meglitinide analogues.
2001 Nov 17
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
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
Effects of S 21403 on hormone secretion from isolated rat pancreas at different glucose concentrations.
2002 Dec 5
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
[Structures and mechanisms for non SU insulin secretagogues].
2002 Sep
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
[Pharmacological and clinical profile of mitiglinide calcium hydrate (Glufast), a new insulinotropic agent with rapid onset].
2004 Oct
[Synthesis and insulinotropic activity of 2-benzylidenesuccinic acid derivatives].
2005 Dec
[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
Determination of mitiglinide in rat plasma by high-performance liquid chromatography with UV detection.
2006 Apr 13
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
Effects of mitiglinide and sulfonylureas in isolated canine coronary arteries and perfused rat hearts.
2006 Feb 15
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
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
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
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
Nateglinide controlled release tablet containing compressionable enteric coated granules.
2010 Sep
Patents

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
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 Jun 26 00:42:51 UTC 2021
Edited
by admin
on Sat Jun 26 00:42:51 UTC 2021
Record UNII
D86I0XLB13
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MITIGLINIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
MITIGLINIDE [WHO-DD]
Common Name English
MITIGLINIDE [MI]
Common Name English
(-)-(2S,3A,7A-CIS)-A-BENZYLHEXAHYDRO-.GAMMA.-OXO-2-ISOINDOLINEBUTYRIC ACID
Common Name English
MITIGLINIDE [INN]
Common Name English
MITIGLINIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C98079
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
WHO-VATC QA10BX08
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
WHO-ATC A10BX08
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
Code System Code Type Description
PUBCHEM
121891
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
INN
7710
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
DRUG BANK
DB01252
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
EVMPD
SUB08999MIG
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
FDA UNII
D86I0XLB13
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
CAS
145375-43-5
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
DRUG CENTRAL
1818
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
MERCK INDEX
M7566
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY Merck Index
MESH
C087255
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
WIKIPEDIA
MITIGLINIDE
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
EPA CompTox
145375-43-5
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
NCI_THESAURUS
C81699
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
ChEMBL
CHEMBL471498
Created by admin on Sat Jun 26 00:42:51 UTC 2021 , Edited by admin on Sat Jun 26 00:42:51 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY