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

HIDE SMILES / InChI

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
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
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	11716850
Rapid acting insulinotropic agents: restoration of early insulin secretion as a physiologic approach to improve glucose control.	2001 Sep	11472274
Study of the insulinotropic effect of the novel antihyperglycemic agent KAD-1229 using HIT T15 cells, a hamster's insulinoma cell line.	2002	12236048
[Mitiglinide (KAD-1229)].	2002 Sep	12387051
[Structures and mechanisms for non SU insulin secretagogues].	2002 Sep	12387019
[Nateglinide and mitiglinide].	2003 Jul	12877090
[Achieving better control of blood sugar--understanding of oral hypoglycemic agents according to their characteristics in pharmacological action mechanism (discussion)].	2004 Apr	15106356
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
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
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	17185877
Mitiglinide, a novel oral hypoglycemic agent, preserves the cardioprotective effect of ischemic preconditioning in isolated perfused rat hearts.	2007 May	17592198
Quantitative determination of mitiglinide in human plasma by ultra-performance liquid chromatography/electrospray ionization tandem mass spectrometry.	2008 Jun 1	18486570
Insulin-releasing activity of a series of phenylalanine derivatives.	2008 Sep	18191001
Postprandial hyperglycemia as an etiological factor in vascular failure.	2009 Apr 29	19402896
Ca(2+) channels on the move.	2009 Dec 29	19928968
[Design, synthesis and hypoglycemic activity of alpha-benzylsuccinic acid derivatives].	2009 May	19618724
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 Nov 1	19748326
Pleiotropic effects of mitiglinide in type 2 diabetes mellitus.	2009 Nov-Dec	20146890
Design of nateglinide controlled release tablet containing erosion matrix tablet and multiple administration study in normal beagle dogs.	2009 Sep	19721250
Efficacy and safety of mitiglinide in diabetic patients on maintenance hemodialysis.	2010	20467165
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
Nateglinide controlled release tablet containing compressionable enteric coated granules.	2010 Sep	20823590
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	26411328

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:21:37 UTC 2023` Edited by `admin` on `Fri Dec 15 16:21:37 UTC 2023`
Record UNII	D86I0XLB13
Record Status	`Validated (UNII)`
Record Version

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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