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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++].[O-]C(=O)[C@H](CC(=O)N1C[C@H]2CCCC[C@H]2C1)CC3=CC=CC=C3.[O-]C(=O)[C@H](CC(=O)N4C[C@H]5CCCC[C@H]5C4)CC6=CC=CC=C6

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 Ca
Molecular Weight 40.078
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

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
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 4.0 nM [IC50]
Inhibitor
8504
 3.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Glufast

Approved Use

Unknown

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
683.2 μg/L
CLINICAL TRIAL
https://link.springer.com/article/10.1007/s40261-012-0012-6
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: Metformin
Metformin
 MITIGLINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
704 μg/L
CLINICAL TRIAL
https://link.springer.com/article/10.1007/s40261-012-0012-6
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: Metformin
Metformin
 MITIGLINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
915.1 μg × h/L
CLINICAL TRIAL
https://link.springer.com/article/10.1007/s40261-012-0012-6
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: Metformin
Metformin
 MITIGLINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1025.5 μg × h/L
CLINICAL TRIAL
https://link.springer.com/article/10.1007/s40261-012-0012-6
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: Metformin
Metformin
 MITIGLINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.19 h
CLINICAL TRIAL
https://link.springer.com/article/10.1007/s40261-012-0012-6
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: Metformin
Metformin
 MITIGLINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.67 h
CLINICAL TRIAL
https://link.springer.com/article/10.1007/s40261-012-0012-6
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered: Metformin
Metformin
 MITIGLINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
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
Mitiglinide: a novel agent for the treatment of type 2 diabetes mellitus.
2010-10
Nateglinide controlled release tablet containing compressionable enteric coated granules.
2010-09
Pleiotropic effects of mitiglinide in type 2 diabetes mellitus.
2010-02-12
Combination therapy with mitiglinide and voglibose improves glycemic control in type 2 diabetic patients on hemodialysis.
2010-02
Efficacy and safety of mitiglinide in diabetic patients on maintenance hemodialysis.
2010
Ca(2+) channels on the move.
2009-12-29
Effect of mitiglinide on Streptozotocin-induced experimental type 2 diabetic rats: a urinary metabonomics study based on ultra-performance liquid chromatography-tandem mass spectrometry.
2009-11-01
Design of nateglinide controlled release tablet containing erosion matrix tablet and multiple administration study in normal beagle dogs.
2009-09
Multicentre, double-blind, randomized study of mitiglinide compared with nateglinide in type 2 diabetes mellitus patients in China.
2009-07-11
[Design, synthesis and hypoglycemic activity of alpha-benzylsuccinic acid derivatives].
2009-05
Postprandial hyperglycemia as an etiological factor in vascular failure.
2009-04-29
Treatment with glimepiride, but not mitiglinide and short-acting insulin, resists body weight and abdominal fat reduction under dietary energy restriction.
2009-03
Effect of insulin-unstimulated diabetic therapy with miglitol on serum cystatin C level and its clinical significance.
2009-01
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
Mitiglinide: a rapid- and short-acting non-sulfonylurea insulinotropic agent for the treatment of type 2 diabetic patients.
2008-10
Insulin-releasing activity of a series of phenylalanine derivatives.
2008-09
Liquid chromatography/electrospray ionization tandem mass spectrometry for the quantification of mitiglinide in human plasma: validation and its application to pharmacokinetic studies.
2008-08
Quantitative determination of mitiglinide in human plasma by ultra-performance liquid chromatography/electrospray ionization tandem mass spectrometry.
2008-06-01
Miglitol increases the adiponectin level and decreases urinary albumin excretion in patients with type 2 diabetes mellitus.
2007-11
Nateglinide and mitiglinide, but not sulfonylureas, induce insulin secretion through a mechanism mediated by calcium release from endoplasmic reticulum.
2007-07
Carboxyl-glucuronidation of mitiglinide by human UDP-glucuronosyltransferases.
2007-06-01
Mitiglinide, a novel oral hypoglycemic agent, preserves the cardioprotective effect of ischemic preconditioning in isolated perfused rat hearts.
2007-05
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.
2007-02
High-performance liquid chromatography-electrospray ionization mass spectrometry determination of mitiglinide in human plasma and its pharmacokinetics.
2007-02
Effect of combination therapy of a rapid-acting insulin secretagogue (glinide) with premixed insulin in type 2 diabetes mellitus.
2007
[Glinide(s), sulfonylurea(s)].
2006-11
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.
2006-10
Determination of mitiglinide in rat plasma by high-performance liquid chromatography with UV detection.
2006-04-13
Effects of mitiglinide on glucose-induced insulin release into the portal vein and fat-induced triglyceride elevation in prediabetic and diabetic OLETF rats.
2006-04
Effects of mitiglinide and sulfonylureas in isolated canine coronary arteries and perfused rat hearts.
2006-02-15
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.
2006-02
[Synthesis and insulinotropic activity of 2-benzylidenesuccinic acid derivatives].
2005-12
[Significance of insulin secretion pattern lectured by "glinides" in the treatment of postprandial hyperglycemia].
2005-12
Characterization of the action of S 21403 (mitiglinide) on insulin secretion and biosynthesis in normal and diabetic beta-cells.
2005-11
Effects of S21403 (mitiglinide) on postprandial generation of oxidative stress and inflammation in type 2 diabetic patients.
2005-09
[Effects of mitiglinide in treatment of impaired glucose tolerance].
2005-02
[Selection of oral antidiabetic drugs].
2005-02
The impact of ATP-sensitive K+ channel subtype selectivity of insulin secretagogues for the coronary vasculature and the myocardium.
2004-12
[Pharmacological and clinical profile of mitiglinide calcium hydrate (Glufast), a new insulinotropic agent with rapid onset].
2004-10
[Achieving better control of blood sugar--understanding of oral hypoglycemic agents according to their characteristics in pharmacological action mechanism (discussion)].
2004-04
Mitiglinide: KAD 1229, S 21403.
2004
[Nateglinide and mitiglinide].
2003-07
[Meglitinide analogs: new insulinotropic agents for the treatment of non-insulin dependent diabetes].
2003-06
Pharmacology of the meglitinide analogs: new treatment options for type 2 diabetes mellitus.
2003
Effects of S 21403 on hormone secretion from isolated rat pancreas at different glucose concentrations.
2002-12-05
[Mitiglinide (KAD-1229)].
2002-09
[Structures and mechanisms for non SU insulin secretagogues].
2002-09
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 Mon Mar 31 21:25:51 GMT 2025
Edited
by admin
on Mon Mar 31 21:25:51 GMT 2025
Record UNII
P5WOR98G68
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MITIGLINIDE CALCIUM
WHO-DD  
Preferred Name English
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 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 Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C132050
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
PRIMARY
EVMPD
SUB25644
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
PRIMARY
PUBCHEM
5478927
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
PRIMARY
MERCK INDEX
m7566
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
PRIMARY
FDA UNII
P5WOR98G68
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
PRIMARY
EVMPD
SUB25643
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
PRIMARY
SMS_ID
100000091418
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
PRIMARY
CAS
145525-41-3
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID90872410
Created by admin on Mon Mar 31 21:25:51 GMT 2025 , Edited by admin on Mon Mar 31 21:25:51 GMT 2025
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
ACTIVE MOIETY
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