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 2004

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
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
[Structures and mechanisms for non SU insulin secretagogues].	2002 Sep	12387019
Pharmacology of the meglitinide analogs: new treatment options for type 2 diabetes mellitus.	2003	15981944
[Synthesis and insulinotropic activity of 2-benzylidenesuccinic acid derivatives].	2005 Dec	16496677
[Effects of mitiglinide in treatment of impaired glucose tolerance].	2005 Feb	15779420
Characterization of the action of S 21403 (mitiglinide) on insulin secretion and biosynthesis in normal and diabetic beta-cells.	2005 Nov	16158072
Effects of S21403 (mitiglinide) on postprandial generation of oxidative stress and inflammation in type 2 diabetic patients.	2005 Sep	16007412
Determination of mitiglinide in rat plasma by high-performance liquid chromatography with UV detection.	2006 Apr 13	16520101
Mitiglinide, a novel oral hypoglycemic agent, preserves the cardioprotective effect of ischemic preconditioning in isolated perfused rat hearts.	2007 May	17592198
Miglitol increases the adiponectin level and decreases urinary albumin excretion in patients with type 2 diabetes mellitus.	2007 Nov	17950094
Mitiglinide: a rapid- and short-acting non-sulfonylurea insulinotropic agent for the treatment of type 2 diabetic patients.	2008 Oct	18803455
Insulin-releasing activity of a series of phenylalanine derivatives.	2008 Sep	18191001
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 GMT 2023` Edited by `admin` on `Fri Dec 15 16:21:37 GMT 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