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
Effect of KAD-1229, a nonsulfonylurea hypoglycemic agent, on plasma glucose and insulin in streptozotocin-induced diabetic dogs.	2001 Feb	11174074
Rapid acting insulinotropic agents: restoration of early insulin secretion as a physiologic approach to improve glucose control.	2001 Sep	11472274
Effects of S 21403 on hormone secretion from isolated rat pancreas at different glucose concentrations.	2002 Dec 5	12450580
[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
[Nateglinide and mitiglinide].	2003 Jul	12877090
[Meglitinide analogs: new insulinotropic agents for the treatment of non-insulin dependent diabetes].	2003 Jun	12891883
Mitiglinide: KAD 1229, S 21403.	2004	15293870
[Achieving better control of blood sugar--understanding of oral hypoglycemic agents according to their characteristics in pharmacological action mechanism (discussion)].	2004 Apr	15106356
The impact of ATP-sensitive K+ channel subtype selectivity of insulin secretagogues for the coronary vasculature and the myocardium.	2004 Dec	15561904
[Pharmacological and clinical profile of mitiglinide calcium hydrate (Glufast), a new insulinotropic agent with rapid onset].	2004 Oct	15467258
[Synthesis and insulinotropic activity of 2-benzylidenesuccinic acid derivatives].	2005 Dec	16496677
[Effects of mitiglinide in treatment of impaired glucose tolerance].	2005 Feb	15779420
[Selection of oral antidiabetic drugs].	2005 Feb	15779417
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
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
Effects of mitiglinide and sulfonylureas in isolated canine coronary arteries and perfused rat hearts.	2006 Feb 15	16443212
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 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
Effect of mitiglinide on glycemic control over 52 weeks in Japanese type 2 diabetic patients insufficiently controlled with pioglitazone monotherapy.	2009	19506328
Postprandial hyperglycemia as an etiological factor in vascular failure.	2009 Apr 29	19402896
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
[Design, synthesis and hypoglycemic activity of alpha-benzylsuccinic acid derivatives].	2009 May	19618724
Efficacy and safety of mitiglinide in diabetic patients on maintenance hemodialysis.	2010	20467165
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 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