MITIGLINIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H25NO3
Molecular Weight	315.4067
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CN(C[C@]1([H])CCCC2)C(=O)C[C@H](CC3=CC=CC=C3)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

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Description
Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/a1d33d0dfec820b41b54430b50e96b5c.html#onlineretailersBasic

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

Targets

Primary Target	Pharmacology	Condition	Potency
Kir6.2/SUR1 3 Target ID: CHEMBL3038487 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11264248	Inhibitor 8297		4.0 nM [IC50]
Sulfonylurea receptor 2, Kir6.2 11 Target ID: CHEMBL2095198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11264248	Inhibitor 8297		3.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/a1d33d0dfec820b41b54430b50e96b5c.html#onlineretailersBasic	Primary		Approved 8429	Glufast Approved Use Unknown Launch Date 1.07524797E12

PubMed

Title	Date	PubMed
Effects of mitiglinide (S 21403) on Kir6.2/SUR1, Kir6.2/SUR2A and Kir6.2/SUR2B types of ATP-sensitive potassium channel.	2001 Apr	11264248
Rapid acting insulinotropic agents: restoration of early insulin secretion as a physiologic approach to improve glucose control.	2001 Sep	11472274
[Mitiglinide (KAD-1229)].	2002 Sep	12387051
Pharmacology of the meglitinide analogs: new treatment options for type 2 diabetes mellitus.	2003	15981944
[Nateglinide and mitiglinide].	2003 Jul	12877090
The impact of ATP-sensitive K+ channel subtype selectivity of insulin secretagogues for the coronary vasculature and the myocardium.	2004 Dec	15561904
[Synthesis and insulinotropic activity of 2-benzylidenesuccinic acid derivatives].	2005 Dec	16496677
Characterization of the action of S 21403 (mitiglinide) on insulin secretion and biosynthesis in normal and diabetic beta-cells.	2005 Nov	16158072
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	16785606
Determination of mitiglinide in rat plasma by high-performance liquid chromatography with UV detection.	2006 Apr 13	16520101
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	16543674
[Glinide(s), sulfonylurea(s)].	2006 Nov	17087304
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	17003348
Effect of combination therapy of a rapid-acting insulin secretagogue (glinide) with premixed insulin in type 2 diabetes mellitus.	2007	18057760
Nateglinide and mitiglinide, but not sulfonylureas, induce insulin secretion through a mechanism mediated by calcium release from endoplasmic reticulum.	2007 Jul	17409272
Carboxyl-glucuronidation of mitiglinide by human UDP-glucuronosyltransferases.	2007 Jun 1	17359941
Mitiglinide: a rapid- and short-acting non-sulfonylurea insulinotropic agent for the treatment of type 2 diabetic patients.	2008 Oct	18803455
Effect of mitiglinide on glycemic control over 52 weeks in Japanese type 2 diabetic patients insufficiently controlled with pioglitazone monotherapy.	2009	19506328
Addition of mitiglinide to pioglitazone monotherapy improves overall glycemic control in Japanese patients with type 2 diabetes: a randomized double blind trial.	2009	19352048
Postprandial hyperglycemia as an etiological factor in vascular failure.	2009 Apr 29	19402896
Ca(2+) channels on the move.	2009 Dec 29	19928968
Effect of insulin-unstimulated diabetic therapy with miglitol on serum cystatin C level and its clinical significance.	2009 Jan	19027977
Treatment with glimepiride, but not mitiglinide and short-acting insulin, resists body weight and abdominal fat reduction under dietary energy restriction.	2009 Mar	19261996
Multicentre, double-blind, randomized study of mitiglinide compared with nateglinide in type 2 diabetes mellitus patients in China.	2009 May-Jun	19589264
Pleiotropic effects of mitiglinide in type 2 diabetes mellitus.	2009 Nov-Dec	20146890
Combination therapy with mitiglinide and voglibose improves glycemic control in type 2 diabetic patients on hemodialysis.	2010 Feb	20025554
Mitiglinide: a novel agent for the treatment of type 2 diabetes mellitus.	2010 Oct	20841518

Patents

Sample Use Guides

In Vivo Use Guide

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.

Name

Type

Language

MITIGLINIDE

Official 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 [WHO-DD]

Common Name

English

MITIGLINIDE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98079