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
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
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 |
---|---|---|---|
Target ID: CHEMBL3038487 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11264248 |
4.0 nM [IC50] | ||
Target ID: CHEMBL2095198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11264248 |
3.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Glufast Approved UseUnknown Launch Date2004 |
PubMed
Title | Date | PubMed |
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Effects of S 21403 on hormone secretion from isolated rat pancreas at different glucose concentrations. | 2002 Dec 5 |
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[Mitiglinide (KAD-1229)]. | 2002 Sep |
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[Structures and mechanisms for non SU insulin secretagogues]. | 2002 Sep |
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Pharmacology of the meglitinide analogs: new treatment options for type 2 diabetes mellitus. | 2003 |
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[Nateglinide and mitiglinide]. | 2003 Jul |
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[Meglitinide analogs: new insulinotropic agents for the treatment of non-insulin dependent diabetes]. | 2003 Jun |
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Mitiglinide: KAD 1229, S 21403. | 2004 |
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[Achieving better control of blood sugar--understanding of oral hypoglycemic agents according to their characteristics in pharmacological action mechanism (discussion)]. | 2004 Apr |
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The impact of ATP-sensitive K+ channel subtype selectivity of insulin secretagogues for the coronary vasculature and the myocardium. | 2004 Dec |
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[Pharmacological and clinical profile of mitiglinide calcium hydrate (Glufast), a new insulinotropic agent with rapid onset]. | 2004 Oct |
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[Synthesis and insulinotropic activity of 2-benzylidenesuccinic acid derivatives]. | 2005 Dec |
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[Significance of insulin secretion pattern lectured by "glinides" in the treatment of postprandial hyperglycemia]. | 2005 Dec |
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[Effects of mitiglinide in treatment of impaired glucose tolerance]. | 2005 Feb |
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[Selection of oral antidiabetic drugs]. | 2005 Feb |
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Characterization of the action of S 21403 (mitiglinide) on insulin secretion and biosynthesis in normal and diabetic beta-cells. | 2005 Nov |
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Effects of S21403 (mitiglinide) on postprandial generation of oxidative stress and inflammation in type 2 diabetic patients. | 2005 Sep |
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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 |
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Determination of mitiglinide in rat plasma by high-performance liquid chromatography with UV detection. | 2006 Apr 13 |
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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 |
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Effects of mitiglinide and sulfonylureas in isolated canine coronary arteries and perfused rat hearts. | 2006 Feb 15 |
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[Glinide(s), sulfonylurea(s)]. | 2006 Nov |
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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 |
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Effect of combination therapy of a rapid-acting insulin secretagogue (glinide) with premixed insulin in type 2 diabetes mellitus. | 2007 |
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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 |
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High-performance liquid chromatography-electrospray ionization mass spectrometry determination of mitiglinide in human plasma and its pharmacokinetics. | 2007 Feb |
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Nateglinide and mitiglinide, but not sulfonylureas, induce insulin secretion through a mechanism mediated by calcium release from endoplasmic reticulum. | 2007 Jul |
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Carboxyl-glucuronidation of mitiglinide by human UDP-glucuronosyltransferases. | 2007 Jun 1 |
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Mitiglinide, a novel oral hypoglycemic agent, preserves the cardioprotective effect of ischemic preconditioning in isolated perfused rat hearts. | 2007 May |
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Miglitol increases the adiponectin level and decreases urinary albumin excretion in patients with type 2 diabetes mellitus. | 2007 Nov |
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Liquid chromatography/electrospray ionization tandem mass spectrometry for the quantification of mitiglinide in human plasma: validation and its application to pharmacokinetic studies. | 2008 Aug |
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Quantitative determination of mitiglinide in human plasma by ultra-performance liquid chromatography/electrospray ionization tandem mass spectrometry. | 2008 Jun 1 |
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Mitiglinide: a rapid- and short-acting non-sulfonylurea insulinotropic agent for the treatment of type 2 diabetic patients. | 2008 Oct |
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Insulin-releasing activity of a series of phenylalanine derivatives. | 2008 Sep |
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Glinide, but not sulfonylurea, can evoke insulin exocytosis by repetitive stimulation: imaging analysis of insulin exocytosis by secretagogue-induced repetitive stimulations. | 2009 |
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Effect of mitiglinide on glycemic control over 52 weeks in Japanese type 2 diabetic patients insufficiently controlled with pioglitazone monotherapy. | 2009 |
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Addition of mitiglinide to pioglitazone monotherapy improves overall glycemic control in Japanese patients with type 2 diabetes: a randomized double blind trial. | 2009 |
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Postprandial hyperglycemia as an etiological factor in vascular failure. | 2009 Apr 29 |
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Ca(2+) channels on the move. | 2009 Dec 29 |
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Effect of insulin-unstimulated diabetic therapy with miglitol on serum cystatin C level and its clinical significance. | 2009 Jan |
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Treatment with glimepiride, but not mitiglinide and short-acting insulin, resists body weight and abdominal fat reduction under dietary energy restriction. | 2009 Mar |
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[Design, synthesis and hypoglycemic activity of alpha-benzylsuccinic acid derivatives]. | 2009 May |
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Multicentre, double-blind, randomized study of mitiglinide compared with nateglinide in type 2 diabetes mellitus patients in China. | 2009 May-Jun |
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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 |
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Pleiotropic effects of mitiglinide in type 2 diabetes mellitus. | 2009 Nov-Dec |
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Design of nateglinide controlled release tablet containing erosion matrix tablet and multiple administration study in normal beagle dogs. | 2009 Sep |
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Efficacy and safety of mitiglinide in diabetic patients on maintenance hemodialysis. | 2010 |
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Combination therapy with mitiglinide and voglibose improves glycemic control in type 2 diabetic patients on hemodialysis. | 2010 Feb |
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Mitiglinide: a novel agent for the treatment of type 2 diabetes mellitus. | 2010 Oct |
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Nateglinide controlled release tablet containing compressionable enteric coated granules. | 2010 Sep |
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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
Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/a1d33d0dfec820b41b54430b50e96b5c.html#onlineretailersBasic
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18191001
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.
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