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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-12-07 02:46:34 UTC
HMDB IDHMDB0014634
Secondary Accession Numbers
  • HMDB14634
Metabolite Identification
Common NameMiglitol
DescriptionMiglitol 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
ValueSource
GlysetKegg
N-Hydroxyethyl-1-desoxy-nojirimycinMeSH
PlumarolMeSH
BAY m 1099MeSH
BAY-m 1099MeSH
BAY-m-1099MeSH
N-Hydroxyethyl-1-desoxynojirimycinMeSH
DiastabolMeSH
Lacer brand OF miglitolMeSH
Sanofi-synthelabo brand OF miglitolMeSH
Miglitol, 4-methylbenzenesulfonate salt, ((D)-isomer)MeSH
Chemical FormulaC8H17NO5
Average Molecular Weight207.2243
Monoisotopic Molecular Weight207.110672659
IUPAC Name(2R,3R,4R,5S)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol
Traditional Namemiglitol
CAS Registry Number72432-03-2
SMILES
OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO
InChI Identifier
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
InChI KeyIBAQFPQHRJAVAV-ULAWRXDQSA-N
Chemical 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
  • 1,2-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Alkanolamine
  • Polyol
  • Azacycle
  • Organic nitrogen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Role

Industrial application:

  Pharmaceutical industry:

    Antimicrobial agent:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point114 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility610 g/LNot Available
LogP-2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility610 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.16 m³·mol⁻¹ChemAxon
Polarizability20.81 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r5-2900000000-56f32f82ba2fcf0b2f3fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0udi-1232790000-441c256496718e67b754View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0950000000-b6d93af11a2ee76dc59eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-2900000000-410b4768b0f8614dc47dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-2900000000-7e4fc39424e628a02185View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0950000000-0a22d4c227ec14f0b1faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a70-1900000000-cd4c33e127797a3d7022View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9100000000-5b937e39803d6010baf9View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00491 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00491 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00491
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390074
KEGG Compound IDC07708
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMiglitol
METLIN IDNot Available
PubChem Compound441314
PDB IDMIG
ChEBI ID545681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Cleaves sequentially the 2 innermost alpha-1,3-linked glucose residues from the Glc(2)Man(9)GlcNAc(2) oligosaccharide precursor of immature glycoproteins.
Gene Name:
GANAB
Uniprot ID:
Q14697
Molecular weight:
Not Available
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. doi: 10.1016/j.ejphar.2009.09.048. Epub 2009 Oct 7. [PubMed:19818342 ]
  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. doi: 10.1055/s-0028-1105919. Epub 2008 Dec 15. [PubMed:19085811 ]
General function:
Involved in catalytic activity
Specific function:
Essential for the degradation of glygogen to glucose in lysosomes.
Gene Name:
GAA
Uniprot ID:
P10253
Molecular weight:
Not Available
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. doi: 10.1016/j.ejphar.2009.09.048. Epub 2009 Oct 7. [PubMed:19818342 ]
  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. doi: 10.1055/s-0028-1105919. Epub 2008 Dec 15. [PubMed:19085811 ]
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
AMY2A
Uniprot ID:
P04746
Molecular weight:
Not Available
General function:
Involved in catalytic activity
Specific function:
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.
Gene Name:
MGAM
Uniprot ID:
O43451
Molecular weight:
Not Available
References
  1. Mooradian AD, Thurman JE: Drug therapy of postprandial hyperglycaemia. Drugs. 1999 Jan;57(1):19-29. [PubMed:9951949 ]
  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:16817895 ]
  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. doi: 10.1016/j.ejphar.2009.09.048. Epub 2009 Oct 7. [PubMed:19818342 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in catalytic activity
Specific function:
Has alpha-glucosidase activity.
Gene Name:
GANC
Uniprot ID:
Q8TET4
Molecular weight:
Not Available
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. doi: 10.1016/j.ejphar.2009.09.048. Epub 2009 Oct 7. [PubMed:19818342 ]
  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. doi: 10.1055/s-0028-1105919. Epub 2008 Dec 15. [PubMed:19085811 ]