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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++].[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=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 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

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

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
Effect of KAD-1229, a nonsulfonylurea hypoglycemic agent, on plasma glucose and insulin in streptozotocin-induced diabetic dogs.
2001 Feb
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
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
[Mitiglinide (KAD-1229)].
2002 Sep
Pharmacology of the meglitinide analogs: new treatment options for type 2 diabetes mellitus.
2003
[Meglitinide analogs: new insulinotropic agents for the treatment of non-insulin dependent diabetes].
2003 Jun
[Achieving better control of blood sugar--understanding of oral hypoglycemic agents according to their characteristics in pharmacological action mechanism (discussion)].
2004 Apr
[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 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
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
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
Postprandial hyperglycemia as an etiological factor in vascular failure.
2009 Apr 29
Ca(2+) channels on the move.
2009 Dec 29
Multicentre, double-blind, randomized study of mitiglinide compared with nateglinide in type 2 diabetes mellitus patients in China.
2009 May-Jun
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

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 Fri Dec 15 16:26:56 UTC 2023
Edited
by admin
on Fri Dec 15 16:26:56 UTC 2023
Record UNII
9651C21W3Z
Record Status Validated (UNII)
Record Version
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Name Type Language
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 SALT DIHYDRATE
MI  
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 Fri Dec 15 16:26:57 UTC 2023 , Edited by admin on Fri Dec 15 16:26:57 UTC 2023
PRIMARY
MERCK INDEX
m7566
Created by admin on Fri Dec 15 16:26:57 UTC 2023 , Edited by admin on Fri Dec 15 16:26:57 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID5046728
Created by admin on Fri Dec 15 16:26:57 UTC 2023 , Edited by admin on Fri Dec 15 16:26:57 UTC 2023
PRIMARY
CAS
207844-01-7
Created by admin on Fri Dec 15 16:26:57 UTC 2023 , Edited by admin on Fri Dec 15 16:26:57 UTC 2023
PRIMARY
EVMPD
SUB21788
Created by admin on Fri Dec 15 16:26:57 UTC 2023 , Edited by admin on Fri Dec 15 16:26:57 UTC 2023
PRIMARY
SMS_ID
100000088882
Created by admin on Fri Dec 15 16:26:57 UTC 2023 , Edited by admin on Fri Dec 15 16:26:57 UTC 2023
PRIMARY
FDA UNII
9651C21W3Z
Created by admin on Fri Dec 15 16:26:57 UTC 2023 , Edited by admin on Fri Dec 15 16:26:57 UTC 2023
PRIMARY
PUBCHEM
6918235
Created by admin on Fri Dec 15 16:26:57 UTC 2023 , Edited by admin on Fri Dec 15 16:26:57 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY