U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H17NO5
Molecular Weight 207.2246
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIGLITOL

SMILES

C(CO)N1C[C@@]([H])([C@]([H])([C@@]([H])([C@@]1([H])CO)O)O)O

InChI

InChIKey=IBAQFPQHRJAVAV-ULAWRXDQSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/cdi/miglitol.html

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. 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. Miglitol is used 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.

CNS Activity

Curator's Comment:: Very low permeation of blood-brain barrier in animals. In humans miglitol is able to cross the blood/brain barrier and potentially inhibit the alpha-glucosidase enzymes of the the central nervous system (CNS) http://press.endocrine.org/doi/abs/10.1210/endo-meetings.2012.DIR.2.SAT-209

Originator

Curator's Comment:: # Bayer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.0 µM [IC50]
2.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
GLYSET

Approved Use

GLYSET is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.

Launch Date

8.5078082E11
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
100 mg 3 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
MIGLITOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 mg 3 times / day multiple, oral
Recommended
Dose: 75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 75 mg, 3 times / day
Sources:
healthy, 39.3
n = 22
Health Status: healthy
Age Group: 39.3
Sex: M
Population Size: 22
Sources:
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (severe, 1 patient)
Sources:
100 mg 3 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 58.4
n = 52
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 58.4
Sex: M+F
Population Size: 52
Sources:
Other AEs: Abdominal discomfort, Diarrhea...
Other AEs:
Abdominal discomfort (26.95%)
Diarrhea (33.9%)
Hypoglycemia (33.9%)
Sources:
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, adult
n = 962
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: adult
Population Size: 962
Sources:
Other AEs: Abdominal pain, Diarrhea...
Other AEs:
Abdominal pain (11.7%)
Diarrhea (28.7%)
Flatulence (41.5%)
Skin rash (4.3%)
Serum iron decreased (9.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea severe, 1 patient
Disc. AE
75 mg 3 times / day multiple, oral
Recommended
Dose: 75 mg, 3 times / day
Route: oral
Route: multiple
Dose: 75 mg, 3 times / day
Sources:
healthy, 39.3
n = 22
Health Status: healthy
Age Group: 39.3
Sex: M
Population Size: 22
Sources:
Abdominal discomfort 26.95%
100 mg 3 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 58.4
n = 52
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 58.4
Sex: M+F
Population Size: 52
Sources:
Diarrhea 33.9%
100 mg 3 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 58.4
n = 52
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 58.4
Sex: M+F
Population Size: 52
Sources:
Hypoglycemia 33.9%
100 mg 3 times / day multiple, oral (max)
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, 58.4
n = 52
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: 58.4
Sex: M+F
Population Size: 52
Sources:
Abdominal pain 11.7%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, adult
n = 962
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: adult
Population Size: 962
Sources:
Diarrhea 28.7%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, adult
n = 962
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: adult
Population Size: 962
Sources:
Skin rash 4.3%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, adult
n = 962
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: adult
Population Size: 962
Sources:
Flatulence 41.5%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, adult
n = 962
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: adult
Population Size: 962
Sources:
Serum iron decreased 9.2%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
unhealthy, adult
n = 962
Health Status: unhealthy
Condition: diabetes mellitus, type 2
Age Group: adult
Population Size: 962
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Critical Importance of alpha-glucosidase contained in rice kernel for alcohol fermentation of rice polish.
2002
Control of post-prandial hyperglycemia--an essential part of good diabetes treatment and prevention of cardiovascular complications.
2002 Apr
C-glycosides and aza-C-glycosides as potential glycosidase and glycosyltransferase inhibitors.
2005
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Synthesis and glycosidase inhibitory activity of new hexa-substituted C8-glycomimetics.
2005 Oct 7
Liquid chromatographic tandem mass spectrometry method for the quantification of miglitol in human plasma.
2006
Inhibition of recombinant human maltase glucoamylase by salacinol and derivatives.
2006 Jun
[Pharmacokinetic, pharmacological, and clinical profile of miglitol (SEIBULE), a novel alpha-glucosidase inhibitor].
2006 Mar
Oxidative stress in type 2 diabetes: the role of fasting and postprandial glycaemia.
2006 Mar
Determination of miglitol in human plasma by liquid chromatography/tandem mass spectrometry.
2007
Divided-dose administration of miglitol just before and 15 minutes after the start of a meal smoothes postprandial plasma glucose excursions and serum insulin responses in healthy men.
2007 Dec
[Iminosugars: current and future therapeutic applications].
2007 Jan
Evaluation of the efficacy, safety and tolerability of miglitol in adult Indian patients with uncomplicated type 2 diabetes mellitus.
2007 Jun
[Adverse effects of alpha-glucosidase inhibitors].
2007 Oct 28
Hypoglycemic and hypolipidemic effects of Saururus chinensis Baill in streptozotocin-induced diabetic rats.
2007 Summer
Alpha-glucosidase-like activity detected in a siboglinid polychaete, Oligobrachia mashikoi.
2008 Apr
Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases.
2008 Nov 24
Comparison of pre- vs. postmeal administration of miglitol for 3 months in type 2 diabetic patients.
2008 Sep
Effect of butanol fraction from Cassia tora L. seeds on glycemic control and insulin secretion in diabetic rats.
2008 Winter
Postprandial hyperglycemia as an etiological factor in vascular failure.
2009 Apr 29
The alpha-glucosidase inhibitor miglitol delays the development of diabetes and dysfunctional insulin secretion in pancreatic beta-cells in OLETF rats.
2009 Dec 10
Acute metabolic responses to a high-carbohydrate meal in outpatients with type 2 diabetes treated with a low-carbohydrate diet: a crossover meal tolerance study.
2009 Dec 29
Effect of insulin-unstimulated diabetic therapy with miglitol on serum cystatin C level and its clinical significance.
2009 Jan
Rapid quantification of miglustat in human plasma and cerebrospinal fluid by liquid chromatography coupled with tandem mass spectrometry.
2009 Jan 15
The alpha-glucosidase inhibitor miglitol suppresses postprandial hyperglycaemia and interleukin-1beta and tumour necrosis factor-alpha gene expression in rat peripheral leucocytes induced by intermittent sucrose loading.
2009 Jul
The alpha-glucosidase inhibitor miglitol decreases glucose fluctuations and gene expression of inflammatory cytokines induced by hyperglycemia in peripheral leukocytes.
2009 Jun
Diabetes treatment.
2009 Mar
Effect of miglitol, an alpha-glucosidase inhibitor, on atherogenic outcomes in balloon-injured diabetic rats.
2009 Mar
Amplification of the inhibitory activity of miglitol by monofluorination.
2009 Oct 1
Drugs associated with more suicidal ideations are also associated with more suicide attempts.
2009 Oct 2
Design, statistical analysis and sample size calculation of a phase IIb/III study of linagliptin versus voglibose and placebo.
2009 Sep 5
Pneumatosis cystoides intestinalis of the ascending colon related to acarbose treatment: a case report.
2009 Sep 8
Pneumatosis cystoides intestinalis induced by the α-glucosidase inhibitor miglitol.
2010
Comparison of adverse gastrointestinal effects of acarbose and miglitol in healthy men: a crossover study.
2010
Effects of pre-meal versus post-meal administration of miglitol on plasma glucagon-like peptide-1 and glucosedependent insulinotropic polypeptide levels in healthy men.
2010
Effects of miglitol, sitagliptin or their combination on plasma glucose, insulin and incretin levels in non-diabetic men.
2010
A case of insulinoma following total gastrectomy--effects of an alpha-glucosidase inhibitor on suppressing GIP and GLP-1 elevations.
2010 Apr
Recommendations for management of diabetes during Ramadan: update 2010.
2010 Aug
The effect of oral antidiabetic agents on A1C levels: a systematic review and meta-analysis.
2010 Aug
Antioxidant rich grape pomace extract suppresses postprandial hyperglycemia in diabetic mice by specifically inhibiting alpha-glucosidase.
2010 Aug 27
The α-glucosidase inhibitor miglitol decreases glucose fluctuations and inflammatory cytokine gene expression in peripheral leukocytes of Japanese patients with type 2 diabetes mellitus.
2010 Dec
Aspects of insulin treatment.
2010 Jan
Glycosidase inhibition: assessing mimicry of the transition state.
2010 Jan 21
Single administration of alpha-glucosidase inhibitors on endothelial function and incretin secretion in diabetic patients with coronary artery disease - Juntendo University trial: effects of miglitol on endothelial vascular reactivity in type 2 diabetic patients with coronary heart disease (J-MACH) -.
2010 Jul
Sitagliptin: review of preclinical and clinical data regarding incidence of pancreatitis.
2010 Jun
Disordered eating behavior in individuals with diabetes: importance of context, evaluation, and classification.
2010 Mar
Glucose supply and insulin demand dynamics of antidiabetic agents.
2010 Mar 1
Type 2 diabetes: postprandial hyperglycemia and increased cardiovascular risk.
2010 Mar 24
Computational identification of uncharacterized cruzain binding sites.
2010 May 11
Acute pancreatitis in type 2 diabetes treated with exenatide or sitagliptin: a retrospective observational pharmacy claims analysis.
2010 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Initial dose: 25 mg orally 3 times a day -After 4 to 8 weeks, may increase to 50 mg orally 3 times a day if needed; after 3 more months, may increase to 100 mg orally 3 times a day if needed based on glycosylated hemoglobin Maintenance dose: 50 mg to 100 mg orally 3 times a day Maximum dose: 100 mg orally 3 times a day
Route of Administration: Oral
In Vitro Use Guide
Miglitol at high concentrations (20-200 uM) inhibited considerably trehalase and lactase (a beta-galactosidase) activities in rat small intestine.
Name Type Language
MIGLITOL
INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
MIGLITOL [VANDF]
Common Name English
NSC-758702
Code English
GLYSET
Brand Name English
MIGLITOL [MART.]
Common Name English
3,4,5-PIPERIDINETRIOL, 1-(2-HYDROXYETHYL)-2-(HYDROXYMETHYL)-, (2R-(2.ALPHA.,3.BETA.,4.ALPHA.,5.BETA.))-
Common Name English
BAY M 1099
Code English
MIGLITOL [JAN]
Common Name English
MIGLITOL [WHO-DD]
Common Name English
BAY-M-1099
Code English
MIGLITOL [INN]
Common Name English
MIGLITOL [USAN]
Common Name English
MIGLITOL [ORANGE BOOK]
Common Name English
MIGLITOL [MI]
Common Name English
(2R,3R,4R,5S)-1-(2-HYDROXYETHYL)-2-(HYDROXYMETHYL)-3,4,5-PIPERIDINETRIOL
Systematic Name English
Classification Tree Code System Code
WHO-VATC QA10BF02
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
NDF-RT N0000175559
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
LIVERTOX 637
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
WHO-ATC A10BF02
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
NCI_THESAURUS C2846
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
NDF-RT N0000000166
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
276-661-6
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
NCI_THESAURUS
C61847
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
MESH
C045621
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
ChEMBL
CHEMBL1561
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
DRUG BANK
DB00491
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
DRUG CENTRAL
1806
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
HSDB
8022
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
EPA CompTox
72432-03-2
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
PUBCHEM
441314
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
MERCK INDEX
M7537
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY Merck Index
RXCUI
30009
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY RxNorm
EVMPD
SUB08958MIG
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
LACTMED
Miglitol
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
IUPHAR
4842
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
INN
5879
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
FDA UNII
0V5436JAQW
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
CAS
72432-03-2
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY
WIKIPEDIA
MIGLITOL
Created by admin on Fri Jun 25 21:56:27 UTC 2021 , Edited by admin on Fri Jun 25 21:56:27 UTC 2021
PRIMARY