U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C19H24NO3.Ca.2H2O
Molecular Weight 704.906
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MITIGLINIDE CALCIUM DIHYDRATE

SMILES

O.O.[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=QEVLNUAVAONTEW-UZYHXJQGSA-L
InChI=1S/2C19H25NO3.Ca.2H2O/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);;2*1H2/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 HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C19H25NO3
Molecular Weight 315.4067
Charge 0
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 18:28:18 GMT 2025
Edited
by admin
on Mon Mar 31 18:28:18 GMT 2025
Record UNII
9651C21W3Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MITIGLINIDE CALCIUM SALT DIHYDRATE
MI  
Preferred Name English
MITIGLINIDE CALCIUM DIHYDRATE
Common Name English
2H-ISOINDOLE-2-BUTANOIC ACID, OCTAHYDRO-.GAMMA.-OXO-.ALPHA.-(PHENYLMETHYL)-, CALCIUM SALT, HYDRATE (2:1:2), (.ALPHA.S,3AR,7AS)-
Common Name English
MITIGLINIDE CALCIUM HYDRATE
Common Name English
GLUFAST
Brand Name English
Mitiglinide calcium dihydrate [WHO-DD]
Common Name English
KAD-1229
Code English
MITIGLINIDE CALCIUM HYDRATE [JAN]
Common Name English
MITIGLINIDE CALCIUM SALT DIHYDRATE [MI]
Common Name English
(S)-2-BENZYL-4-OXO-4-(CIS-PERHYDROISOINDOL-2-YL)BUTYRIC ACID CALCIUM SALT DIHYDRATE
Common Name English
S-21403
Code English
BIS((2S)-2-BENZYL-3-(CIS-HEXAHYDROISOINDOLIN-2-YLCARBONYL)PROPIONATE) CALCIUM DIHYDRATE, D-
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT001868
Created by admin on Mon Mar 31 18:28:18 GMT 2025 , Edited by admin on Mon Mar 31 18:28:18 GMT 2025
PRIMARY
MERCK INDEX
m7566
Created by admin on Mon Mar 31 18:28:18 GMT 2025 , Edited by admin on Mon Mar 31 18:28:18 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID5046728
Created by admin on Mon Mar 31 18:28:18 GMT 2025 , Edited by admin on Mon Mar 31 18:28:18 GMT 2025
PRIMARY
CAS
207844-01-7
Created by admin on Mon Mar 31 18:28:18 GMT 2025 , Edited by admin on Mon Mar 31 18:28:18 GMT 2025
PRIMARY
EVMPD
SUB21788
Created by admin on Mon Mar 31 18:28:18 GMT 2025 , Edited by admin on Mon Mar 31 18:28:18 GMT 2025
PRIMARY
SMS_ID
100000088882
Created by admin on Mon Mar 31 18:28:18 GMT 2025 , Edited by admin on Mon Mar 31 18:28:18 GMT 2025
PRIMARY
FDA UNII
9651C21W3Z
Created by admin on Mon Mar 31 18:28:18 GMT 2025 , Edited by admin on Mon Mar 31 18:28:18 GMT 2025
PRIMARY
PUBCHEM
6918235
Created by admin on Mon Mar 31 18:28:18 GMT 2025 , Edited by admin on Mon Mar 31 18:28:18 GMT 2025
PRIMARY
Related Record Type Details
Structure of MITIGLINIDE CALCIUM ANHYDROUS
ANHYDROUS->SOLVATE
Structure of MITIGLINIDE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of MITIGLINIDE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966