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Identification
NameMiglitol
Accession NumberDB00491  (APRD01117)
TypeSmall Molecule
GroupsApproved
Description

Miglitol is an oral anti-diabetic drug that acts by inhibiting the ability of the patient to breakdown complex carbohydrates into glucose. It is primarily used in diabetes mellitus type 2 for establishing greater glycemic control by preventing the digestion of carbohydrates (such as disaccharides, oligosaccharides, and polysaccharides) into monosaccharides which can be absorbed by the body.

Miglitol inhibits glycoside hydrolase enzymes called alpha-glucosidases. Since miglitol works by preventing digestion of carbohydrates, it lowers the degree of postprandial hyperglycemia. It must be taken at the start of main meals to have maximal effect. Its effect will depend on the amount of non-monosaccharide carbohydrates in a person’s diet.

In contrast to acarbose (another alpha-glucosidase inhibitor), miglitol is systemically absorbed; however, it is not metabolized and is excreted by the kidneys.

Structure
Thumb
Synonyms
SynonymLanguageCode
GlysetNot AvailableNot Available
MiglitolFrench/German/SpanishINN
MiglitolumLatinINN
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Glysettablet, film coated25 mgoralPharmacia and Upjohn Company1996-12-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glysettablet, film coated50 mgoralPharmacia and Upjohn Company1996-12-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Glysettablet, film coated100 mgoralPharmacia and Upjohn Company1996-12-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
DiabanChen Ho
DiamigMicro DTF
DiasetACI
DiastabolSanofi-Aventis
ElitoxRanbaxy
EuglitolAbbott
GlycetPfizer
LaipingXinchang Pharmaceutical
MigboseStandard
MiglitBiocon
MignarGlenmark
MigtorTorrent
MisobitLupin
PlumarolLacer
SeibuleSanwa Kagaku
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number72432-03-2
WeightAverage: 207.2243
Monoisotopic: 207.110672659
Chemical FormulaC8H17NO5
InChI KeyIBAQFPQHRJAVAV-ULAWRXDQSA-N
InChI
InChI=1S/C8H17NO5/c10-2-1-9-3-6(12)8(14)7(13)5(9)4-11/h5-8,10-14H,1-4H2/t5-,6+,7-,8-/m1/s1
IUPAC Name
(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
SMILES
OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as piperidines. These are compounds containing a piperidine ring, which is a saturated aliphatic six-member ring with one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassNot Available
Direct ParentPiperidines
Alternative Parents
Substituents
  • Piperidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Azacycle
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor use as an adjunct to diet to improve glycemic control in patients with non-insulin-dependent diabetes mellitus (NIDDM) whose hyperglycemia cannot be managed with diet alone.
PharmacodynamicsMiglitol, an oral alpha-glucosidase inhibitor, is a desoxynojirimycin derivative that delays the digestion of ingested carbohydrates, thereby resulting in a smaller rise in blood glucose concentration following meals. As a consequence of plasma glucose reduction, miglitol reduce levels of glycosylated hemoglobin in patients with Type II (non-insulin-dependent) diabetes mellitus. Systemic nonenzymatic protein glycosylation, as reflected by levels of glycosylated hemoglobin, is a function of average blood glucose concentration over time. Because its mechanism of action is different, the effect of miglitol to enhance glycemic control is additive to that of sulfonylureas when used in combination. In addition, miglitol diminishes the insulinotropic and weight-increasing effects of sulfonylureas. Miglitol has minor inhibitory activity against lactase and consequently, at the recommended doses, would not be expected to induce lactose intolerance.
Mechanism of actionIn contrast to sulfonylureas, miglitol does not enhance insulin secretion. The antihyperglycemic action of miglitol results from a reversible inhibition of membrane-bound intestinal a-glucoside hydrolase enzymes. Membrane-bound intestinal a-glucosidases hydrolyze oligosaccharides and disaccharides to glucose and other monosaccharides in the brush border of the small intestine. In diabetic patients, this enzyme inhibition results in delayed glucose absorption and lowering of postprandial hyperglycemia.
AbsorptionAbsorption of miglitol is saturable at high doses with 25 mg being completely absorbed while a 100-mg dose is only 50-70% absorbed. No evidence exists to show that systemic absorption of miglitol adds to its therapeutic effect.
Volume of distribution
  • 0.18 L/kg
Protein bindingThe protein binding of miglitol is negligible (<4.0%).
Metabolism

Miglitol is not metabolized in man or in any animal species studied.

Route of eliminationMiglitol is not metabolized in man or in any animal species studied. It is eliminated by renal excretion as an unchanged drug.
Half lifeThe elimination half-life of miglitol from plasma is approximately 2 hours.
ClearanceNot Available
ToxicityUnlike sulfonylureas or insulin, an overdose will not result in hypoglycemia. An overdose may result in transient increases in flatulence, diarrhea, and abdomi-nal discomfort. Because of the lack of extra-intestinal effects seen with miglitol, no serious systemic reactions are expected in the event of an overdose.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5422
Blood Brain Barrier-0.8379
Caco-2 permeable-0.7375
P-glycoprotein substrateSubstrate0.6354
P-glycoprotein inhibitor INon-inhibitor0.7325
P-glycoprotein inhibitor IINon-inhibitor0.8248
Renal organic cation transporterNon-inhibitor0.6749
CYP450 2C9 substrateNon-substrate0.8563
CYP450 2D6 substrateNon-substrate0.8168
CYP450 3A4 substrateNon-substrate0.6208
CYP450 1A2 substrateNon-inhibitor0.927
CYP450 2C9 substrateNon-inhibitor0.9022
CYP450 2D6 substrateNon-inhibitor0.9535
CYP450 2C19 substrateNon-inhibitor0.9676
CYP450 3A4 substrateNon-inhibitor0.9931
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9968
Ames testNon AMES toxic0.79
CarcinogenicityNon-carcinogens0.9702
BiodegradationNot ready biodegradable0.5392
Rat acute toxicity1.7432 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5797
hERG inhibition (predictor II)Non-inhibitor0.8756
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Tablet, film coatedoral100 mg
Tablet, film coatedoral25 mg
Tablet, film coatedoral50 mg
Prices
Unit descriptionCostUnit
Glyset 100 mg tablet1.46USD tablet
Glyset 50 mg tablet1.24USD tablet
Glyset 25 mg tablet1.11USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point114 °CNot Available
water solubilitySolubleNot Available
logP-2.7Not Available
pKa5.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility610.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-3.2ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)12.9ChemAxon
pKa (Strongest Basic)7.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area104.39 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.16 m3·mol-1ChemAxon
Polarizability20.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesA10BF02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (68.8 KB)
Interactions
Drug Interactions
Drug
AcetohexamideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Acetylsalicylic acidMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents.
BuforminAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
ChlorpropamideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
DihydrotestosteroneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
ExenatideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
GliclazideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
GlimepirideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
GlipizideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Glucagon recombinantAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
GlyburideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin AspartAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin GlargineAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin LisproAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin, isophaneAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Insulin, porcineAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
MitiglinideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
NateglinideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
OxandroloneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PegvisomantMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents.
PhenforminAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
PioglitazoneAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
RepaglinideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Salicylate-sodiumMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents.
SulodexideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
TestosteroneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
TolbutamideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
Food Interactions
  • Take with food, at beginning of each meal. Iron needs increased.

Targets

1. Maltase-glucoamylase, intestinal

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist inhibitor

Components

Name UniProt ID Details
Maltase-glucoamylase, intestinal O43451 Details

References:

  1. Mooradian AD, Thurman JE: Drug therapy of postprandial hyperglycaemia. Drugs. 1999 Jan;57(1):19-29. Pubmed
  2. Rossi EJ, Sim L, Kuntz DA, Hahn D, Johnston BD, Ghavami A, Szczepina MG, Kumar NS, Sterchi EE, Nichols BL, Pinto BM, Rose DR: Inhibition of recombinant human maltase glucoamylase by salacinol and derivatives. FEBS J. 2006 Jun;273(12):2673-83. Pubmed
  3. Fukaya N, Mochizuki K, Tanaka Y, Kumazawa T, Jiuxin Z, Fuchigami M, Goda T: The alpha-glucosidase inhibitor miglitol delays the development of diabetes and dysfunctional insulin secretion in pancreatic beta-cells in OLETF rats. Eur J Pharmacol. 2009 Dec 10;624(1-3):51-7. Epub 2009 Oct 7. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Lysosomal alpha-glucosidase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Lysosomal alpha-glucosidase P10253 Details

References:

  1. Fukaya N, Mochizuki K, Tanaka Y, Kumazawa T, Jiuxin Z, Fuchigami M, Goda T: The alpha-glucosidase inhibitor miglitol delays the development of diabetes and dysfunctional insulin secretion in pancreatic beta-cells in OLETF rats. Eur J Pharmacol. 2009 Dec 10;624(1-3):51-7. Epub 2009 Oct 7. Pubmed
  2. Hirata A, Igarashi M, Iwai H, Tominaga M: Effect of miglitol, an alpha-glucosidase inhibitor, on atherogenic outcomes in balloon-injured diabetic rats. Horm Metab Res. 2009 Mar;41(3):213-20. Epub 2008 Dec 15. Pubmed

3. Neutral alpha-glucosidase AB

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Neutral alpha-glucosidase AB Q14697 Details

References:

  1. Fukaya N, Mochizuki K, Tanaka Y, Kumazawa T, Jiuxin Z, Fuchigami M, Goda T: The alpha-glucosidase inhibitor miglitol delays the development of diabetes and dysfunctional insulin secretion in pancreatic beta-cells in OLETF rats. Eur J Pharmacol. 2009 Dec 10;624(1-3):51-7. Epub 2009 Oct 7. Pubmed
  2. Hirata A, Igarashi M, Iwai H, Tominaga M: Effect of miglitol, an alpha-glucosidase inhibitor, on atherogenic outcomes in balloon-injured diabetic rats. Horm Metab Res. 2009 Mar;41(3):213-20. Epub 2008 Dec 15. Pubmed

4. Neutral alpha-glucosidase C

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Neutral alpha-glucosidase C Q8TET4 Details

References:

  1. Fukaya N, Mochizuki K, Tanaka Y, Kumazawa T, Jiuxin Z, Fuchigami M, Goda T: The alpha-glucosidase inhibitor miglitol delays the development of diabetes and dysfunctional insulin secretion in pancreatic beta-cells in OLETF rats. Eur J Pharmacol. 2009 Dec 10;624(1-3):51-7. Epub 2009 Oct 7. Pubmed
  2. Hirata A, Igarashi M, Iwai H, Tominaga M: Effect of miglitol, an alpha-glucosidase inhibitor, on atherogenic outcomes in balloon-injured diabetic rats. Horm Metab Res. 2009 Mar;41(3):213-20. Epub 2008 Dec 15. Pubmed

Enzymes

1. Pancreatic alpha-amylase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Pancreatic alpha-amylase P04746 Details
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10