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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

2004
PubMed

PubMed

TitleDatePubMed
Effect of KAD-1229, a nonsulfonylurea hypoglycemic agent, on plasma glucose and insulin in streptozotocin-induced diabetic dogs.
2001 Feb
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
Effects of S 21403 on hormone secretion from isolated rat pancreas at different glucose concentrations.
2002 Dec 5
[Significance of insulin secretion pattern lectured by "glinides" in the treatment of postprandial hyperglycemia].
2005 Dec
Characterization of the action of S 21403 (mitiglinide) on insulin secretion and biosynthesis in normal and diabetic beta-cells.
2005 Nov
Effects of mitiglinide and sulfonylureas in isolated canine coronary arteries and perfused rat hearts.
2006 Feb 15
[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
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
Effect of mitiglinide on glycemic control over 52 weeks in Japanese type 2 diabetic patients insufficiently controlled with pioglitazone monotherapy.
2009
Ca(2+) channels on the move.
2009 Dec 29
Combination therapy with mitiglinide and voglibose improves glycemic control in type 2 diabetic patients on hemodialysis.
2010 Feb
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 GMT 2023
Edited
by admin
on Fri Dec 15 16:26:56 GMT 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 GMT 2023 , Edited by admin on Fri Dec 15 16:26:57 GMT 2023
PRIMARY
MERCK INDEX
m7566
Created by admin on Fri Dec 15 16:26:57 GMT 2023 , Edited by admin on Fri Dec 15 16:26:57 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID5046728
Created by admin on Fri Dec 15 16:26:57 GMT 2023 , Edited by admin on Fri Dec 15 16:26:57 GMT 2023
PRIMARY
CAS
207844-01-7
Created by admin on Fri Dec 15 16:26:57 GMT 2023 , Edited by admin on Fri Dec 15 16:26:57 GMT 2023
PRIMARY
EVMPD
SUB21788
Created by admin on Fri Dec 15 16:26:57 GMT 2023 , Edited by admin on Fri Dec 15 16:26:57 GMT 2023
PRIMARY
SMS_ID
100000088882
Created by admin on Fri Dec 15 16:26:57 GMT 2023 , Edited by admin on Fri Dec 15 16:26:57 GMT 2023
PRIMARY
FDA UNII
9651C21W3Z
Created by admin on Fri Dec 15 16:26:57 GMT 2023 , Edited by admin on Fri Dec 15 16:26:57 GMT 2023
PRIMARY
PUBCHEM
6918235
Created by admin on Fri Dec 15 16:26:57 GMT 2023 , Edited by admin on Fri Dec 15 16:26:57 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY