Identification
- Generic Name
- Mitiglinide
- DrugBank Accession Number
- DB01252
- Background
Mitiglinide is a drug for the treatment of type 2 diabetes. It may stimulate insulin secretion in beta-cells by closing off ATP dependant potassium ion channels.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Mitiglinide (DB01252)
- Weight
- Average: 315.413
Monoisotopic: 315.183443669 - Chemical Formula
- C19H25NO3
- Synonyms
- Mitiglinide
Pharmacology
- Indication
For the treatment of type 2 diabetes.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Mitiglinide belongs to the meglitinide class of blood glucose-lowering drugs. It is approved for use in Japan but has not yet gained FDA approval.
- Mechanism of action
Mitiglinide is thought to stimulate insulin secretion by binding to and blocking ATP-sensitive K(+) (K(ATP)) channels (Kir6.2/SUR1 complex, KATP channels) in pancreatic beta-cells. Closure of potassium channels causes depolarization which stimulates calcium influx through voltage-gated calcium channels. High intracellular calcium subsequently triggers the exocytosis of insulin granules.
Target Actions Organism AATP-binding cassette sub-family C member 8 inhibitorHumans UPeroxisome proliferator-activated receptor gamma agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The risk or severity of hypoglycemia can be increased when Acarbose is combined with Mitiglinide. Acebutolol The therapeutic efficacy of Mitiglinide can be increased when used in combination with Acebutolol. Acetazolamide The therapeutic efficacy of Mitiglinide can be increased when used in combination with Acetazolamide. Acetohexamide The risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Mitiglinide. Acetyl sulfisoxazole The therapeutic efficacy of Mitiglinide can be increased when used in combination with Acetyl sulfisoxazole. Acetylsalicylic acid The risk or severity of hypoglycemia can be increased when Acetylsalicylic acid is combined with Mitiglinide. Albiglutide The risk or severity of hypoglycemia can be increased when Mitiglinide is combined with Albiglutide. Alclometasone The risk or severity of hyperglycemia can be increased when Alclometasone is combined with Mitiglinide. Alogliptin The risk or severity of hypoglycemia can be increased when Mitiglinide is combined with Alogliptin. Amcinonide The risk or severity of hyperglycemia can be increased when Amcinonide is combined with Mitiglinide. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Mitiglinide calcium dihydrate 9651C21W3Z 207844-01-7 QEVLNUAVAONTEW-UZYHXJQGSA-L - International/Other Brands
- Glufast
Categories
- ATC Codes
- A10BX08 — Mitiglinide
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Phenylpropanoic acids
- Sub Class
- Not Available
- Direct Parent
- Phenylpropanoic acids
- Alternative Parents
- Isoindolines / Isoindoles / N-acylpyrrolidines / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 3 more
- Substituents
- 3-phenylpropanoic-acid / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Isoindole show 14 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- D86I0XLB13
- CAS number
- 145375-43-5
- InChI Key
- WPGGHFDDFPHPOB-BBWFWOEESA-N
- InChI
- 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
- IUPAC Name
- (2S)-4-[(3aR,7aS)-octahydro-1H-isoindol-2-yl]-2-benzyl-4-oxobutanoic acid
- SMILES
- [H][C@@](CC(=O)N1C[C@@]2([H])CCCC[C@@]2([H])C1)(CC1=CC=CC=C1)C(O)=O
References
- General References
- Not Available
- External Links
- KEGG Drug
- D01854
- PubChem Compound
- 121891
- PubChem Substance
- 46506527
- ChemSpider
- 108739
- ChEBI
- 135349
- ChEMBL
- CHEMBL471498
- ZINC
- ZINC000001482913
- Therapeutic Targets Database
- DAP000917
- PharmGKB
- PA164748124
- PDBe Ligand
- 9I0
- Wikipedia
- Mitiglinide
- PDB Entries
- 7wit
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Not Available Type 2 Diabetes Mellitus 1 4 Completed Treatment Hepatic dysfunction / Type 2 Diabetes Mellitus 1 4 Completed Treatment Type 2 Diabetes Mellitus 3 4 Unknown Status Treatment BMI >27 kg/m2 / Masked Hypertension / Obesity / Type 2 Diabetes Mellitus 1 3 Completed Treatment Diabetes 1 3 Completed Treatment Type 2 Diabetes Mellitus 3 1 Completed Not Available Healthy Subjects (HS) 1 1 Completed Not Available Healthy Subjects (HS) / Pharmacokinetics of ASP1941 / Pharmacokinetics of Mitiglinide 1 1 Completed Treatment Type 2 Diabetes Mellitus 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet 10 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.9 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0708 mg/mL ALOGPS logP 3.17 ALOGPS logP 2.92 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 4.62 Chemaxon pKa (Strongest Basic) -0.83 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 57.61 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 88.31 m3·mol-1 Chemaxon Polarizability 34.98 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9921 Blood Brain Barrier + 0.9694 Caco-2 permeable - 0.5956 P-glycoprotein substrate Substrate 0.5 P-glycoprotein inhibitor I Non-inhibitor 0.6887 P-glycoprotein inhibitor II Non-inhibitor 0.8357 Renal organic cation transporter Inhibitor 0.5235 CYP450 2C9 substrate Non-substrate 0.8241 CYP450 2D6 substrate Non-substrate 0.6396 CYP450 3A4 substrate Non-substrate 0.5135 CYP450 1A2 substrate Non-inhibitor 0.765 CYP450 2C9 inhibitor Non-inhibitor 0.8653 CYP450 2D6 inhibitor Non-inhibitor 0.9234 CYP450 2C19 inhibitor Non-inhibitor 0.6464 CYP450 3A4 inhibitor Non-inhibitor 0.8786 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8753 Ames test Non AMES toxic 0.7059 Carcinogenicity Non-carcinogens 0.95 Biodegradation Ready biodegradable 0.522 Rat acute toxicity 2.3334 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8826 hERG inhibition (predictor II) Non-inhibitor 0.7529
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sulfonylurea receptor activity
- Specific Function
- Subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release.
- Gene Name
- ABCC8
- Uniprot ID
- Q09428
- Uniprot Name
- ATP-binding cassette sub-family C member 8
- Molecular Weight
- 176990.36 Da
References
- Sunaga Y, Gonoi T, Shibasaki T, Ichikawa K, Kusama H, Yano H, Seino S: 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. Eur J Pharmacol. 2001 Nov 9;431(1):119-25. [Article]
- Nagamatsu S, Ohara-Imaizumi M, Nakamichi Y, Kikuta T, Nishiwaki C: 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. Diabetes. 2006 Oct;55(10):2819-25. [Article]
- Ogawa K, Ikewaki K, Taniguchi I, Takatsuka H, Mori C, Sasaki H, Okazaki F, Shimizu M, Mochizuki S: Mitiglinide, a novel oral hypoglycemic agent, preserves the cardioprotective effect of ischemic preconditioning in isolated perfused rat hearts. Int Heart J. 2007 May;48(3):337-45. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
- Gene Name
- PPARG
- Uniprot ID
- P37231
- Uniprot Name
- Peroxisome proliferator-activated receptor gamma
- Molecular Weight
- 57619.58 Da
References
- Scarsi M, Podvinec M, Roth A, Hug H, Kersten S, Albrecht H, Schwede T, Meyer UA, Rucker C: Sulfonylureas and glinides exhibit peroxisome proliferator-activated receptor gamma activity: a combined virtual screening and biological assay approach. Mol Pharmacol. 2007 Feb;71(2):398-406. Epub 2006 Nov 2. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Drug created at March 30, 2007 18:07 / Updated at February 21, 2021 18:51