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Identification
Name Miglitol
Accession Number DB00491 (APRD01117)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Glyset
Brand mixtures Not Available
Categories
  • Hypoglycemic Agents
  • Anti-Bacterial Agents
  • Enzyme Inhibitors
CAS number 72432-03-2
Weight Average: 207.2243
Monoisotopic: 207.110672659
Chemical Formula C8H17NO5
InChI Key InChIKey=IBAQFPQHRJAVAV-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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Glycerol and Derivatives
  • Piperidines
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Alcohols and Polyols
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
  • Piperidines
Pharmacology
Indication For 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.
Pharmacodynamics Miglitol, 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 action In 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.
Absorption Absorption 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 binding The protein binding of miglitol is negligible (<4.0%).
Metabolism Miglitol is not metabolized in man or in any animal species studied.
Route of elimination Miglitol is not metabolized in man or in any animal species studied. It is eliminated by renal excretion as an unchanged drug.
Half life The elimination half-life of miglitol from plasma is approximately 2 hours.
Clearance Not Available
Toxicity Unlike 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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Glyset 100 mg tablet 1.46 USD tablet
Glyset 50 mg tablet 1.24 USD tablet
Glyset 25 mg tablet 1.11 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 114 °C Not Available
water solubility Soluble Not Available
logP -2.7 Not Available
pKa 5.9 Not Available
Predicted Properties
Property Value Source
water solubility 6.10e+02 g/l ALOGPS
logP -2.3 ALOGPS
logP -3.2 ChemAxon
logS 0.47 ALOGPS
pKa (strongest acidic) 12.9 ChemAxon
pKa (strongest basic) 7.6 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 5 ChemAxon
polar surface area 104.39 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 48.16 ChemAxon
polarizability 20.81 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00625 Link_out
KEGG Compound C07708 Link_out
PubChem Compound 441314 Link_out
PubChem Substance 46504492 Link_out
ChemSpider 390074 Link_out
Therapeutic Targets Database DAP000712 Link_out
PharmGKB PA164776726 Link_out
RxList http://www.rxlist.com/cgi/generic2/miglitol.htm Link_out
Drugs.com http://www.drugs.com/cdi/miglitol.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Miglitol Link_out
ATC Codes
  • A10BF02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (68.8 KB)
Interactions
Drug Interactions
Drug Interaction
Glucosamine Possible hyperglycemia
Somatropin recombinant Somatropin may antagonize the hypoglycemic effect of miglitol. Monitor for changes in fasting and postprandial blood sugars.
Food Interactions
  • Take with food, at beginning of each meal. Iron needs increased.
Targets

1. Maltase-glucoamylase, intestinal

Pharmacological action: yes
Actions: antagonist, inhibitor

May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing

Organism class: human
UniProt ID: O43451 Link_out
Gene: MGAM Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: antagonist

Essential for the degradation of glygogen to glucose in lysosomes

Organism class: human
UniProt ID: P10253 Link_out
Gene: GAA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: antagonist
UniProt ID: Q14697 Link_out

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

Pharmacological action: yes
Actions: antagonist
UniProt ID: Q8TET4 Link_out

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

Endohydrolysis of 1,4-alpha-D-glucosidic linkages in oligosaccharides and polysaccharides

UniProt ID: P04746 Link_out
Gene: AMY2A
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19