Voglibose

Identification

Summary

Voglibose is an alpha-glucosidase inhibitor indicated in the management of postprandial blood glucose in patients with type II diabetes.

Generic Name
Voglibose
DrugBank Accession Number
DB04878
Background

Voglibose is an alpha-glucosidase inhibitor used for lowering post-prandial blood glucose levels in people with diabetes mellitus. It is made in India by Ranbaxy Labs and sold under the trade name Volix.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 267.2762
Monoisotopic: 267.131802031
Chemical Formula
C10H21NO7
Synonyms
  • Voglibosa
  • Voglibose
  • Voglibosum
External IDs
  • A-71100
  • AO 128
  • AO-128

Pharmacology

Indication

For the treatment of diabetes. It is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications.

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Voglibose, an alpha-glucosidase inhibitor, is a synthetic compound with potent and enduring therapeutic efficacies against disorders of sensory, motor and autonomic nerve systems due to diabetes mellitus. The drug was approved in Japan in 1994 for the treatment of diabetes, and it is under further investigation by Takeda for the treatment of impaired glucose tolerance. Alpha-glucosidase inhibitors are oral anti-diabetic drugs used for diabetes mellitus type 2 that work by preventing the digestion of complex carbohydrates (such as starch). Complex carbohydrates are normally converted into simple sugars (monosaccharides) which can be absorbed through the intestine. Hence, alpha-glucosidase inhibitors reduce the impact of complex carbohydrates on blood sugar.

Mechanism of action

Alpha-glucosidase inhibitors are saccharides that act as competitive inhibitors of enzymes needed to digest carbohydrates: specifically alpha-glucosidase enzymes in the brush border of the small intestines. The membrane-bound intestinal alpha-glucosidases hydrolyze oligosaccharides, trisaccharides, and disaccharides to glucose and other monosaccharides in the small intestine. Acarbose also blocks pancreatic alpha-amylase in addition to inhibiting membrane-bound alpha-glucosidases. Pancreatic alpha-amylase hydrolyzes complex starches to oligosaccharides in the lumen of the small intestine. Inhibition of these enzyme systems reduces the rate of digestion of complex carbohydrates. Less glucose is absorbed because the carbohydrates are not broken down into glucose molecules. In diabetic patients, the short-term effect of these drugs therapies is to decrease current blood glucose levels: the long term effect is a small reduction in hemoglobin-A1c level. (From Drug Therapy in Nursing, 2nd ed)

TargetActionsOrganism
AMaltase-glucoamylase, intestinal
inhibitor
Humans
Absorption

Slowly and poorly absorbed. The reported pharmacokinetic parameters of voglibose with metformin are Cmax corresponds to 1.38 mcg/ml while AUC is 8.17 mcg.h/ml and tmax is of 2.5 hours.4

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Little metabolism occurs and no metabolites have as yet been identified.

Route of elimination

Not Available

Half-life

The half-life of voglibose is very similar to the one found for metformin and it is reported to be of 4.08 hours.4

Clearance

Not Available

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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.
DrugInteraction
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Voglibose.
AcebutololThe therapeutic efficacy of Voglibose can be increased when used in combination with Acebutolol.
AcetazolamideThe therapeutic efficacy of Voglibose can be increased when used in combination with Acetazolamide.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Voglibose.
Acetyl sulfisoxazoleThe therapeutic efficacy of Voglibose can be increased when used in combination with Acetyl sulfisoxazole.
Acetylsalicylic acidThe risk or severity of hypoglycemia can be increased when Acetylsalicylic acid is combined with Voglibose.
AlbiglutideThe risk or severity of hypoglycemia can be increased when Voglibose is combined with Albiglutide.
AlclometasoneThe risk or severity of hyperglycemia can be increased when Alclometasone is combined with Voglibose.
AlogliptinThe risk or severity of hypoglycemia can be increased when Voglibose is combined with Alogliptin.
AmcinonideThe risk or severity of hyperglycemia can be increased when Amcinonide is combined with Voglibose.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
Not Available

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
Basen (Takeda Chemical Industries) / Glustat / Volix (Ranbaxy labs)

Categories

ATC Codes
A10BF03 — Voglibose
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminocyclitols. These are cyclitols with at least one hydroxyl group replace by an amino group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Aminocyclitols
Alternative Parents
Cyclohexylamines / Cyclohexanols / Tertiary alcohols / 1,2-aminoalcohols / Polyols / Dialkylamines / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1,2-aminoalcohol / Aliphatic homomonocyclic compound / Amine / Aminocyclitol / Cyclohexanol / Cyclohexylamine / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
S77P977AG8
CAS number
83480-29-9
InChI Key
FZNCGRZWXLXZSZ-CIQUZCHMSA-N
InChI
InChI=1S/C10H21NO7/c12-2-5(3-13)11-6-1-10(18,4-14)9(17)8(16)7(6)15/h5-9,11-18H,1-4H2/t6-,7-,8+,9-,10-/m0/s1
IUPAC Name
(1S,2S,3R,4S,5S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
SMILES
OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O

References

Synthesis Reference

Heinz G. Floss, Sungsook Lee, Ingo Tornus, "Valiolone, a method of preparing it, and its use to prepare acarbose and voglibose." U.S. Patent US6150568, issued October, 1995.

US6150568
General References
  1. Aso Y, Yamamoto R, Suetsugu M, Matsumoto S, Wakabayashi S, Matsutomo R, Takebayashi K, Inukai T: Comparison of the effects of pioglitazone and voglibose on circulating total and high-molecular-weight adiponectin, and on two fibrinolysis inhibitors, in patients with Type 2 diabetes. Diabet Med. 2007 Sep;24(9):962-8. Epub 2007 May 17. [Article]
  2. Kurebayashi S, Watada H, Tanaka Y, Kawasumi M, Kawamori R, Hirose T: Efficacy and adverse effects of nateglinide in early type 2 diabetes. Comparison with voglibose in a cross-over study. Endocr J. 2006 Apr;53(2):213-7. [Article]
  3. Satoh N, Shimatsu A, Yamada K, Aizawa-Abe M, Suganami T, Kuzuya H, Ogawa Y: An alpha-glucosidase inhibitor, voglibose, reduces oxidative stress markers and soluble intercellular adhesion molecule 1 in obese type 2 diabetic patients. Metabolism. 2006 Jun;55(6):786-93. [Article]
  4. Choi HK, Oh M, Kim EJ, Song GS, Ghim JL, Shon JH, Kim HS, Shin JG: Pharmacokinetic study of metformin to compare voglibose/metformin fixed-dose combination with coadministered voglibose and metformin. Int J Clin Pharmacol Ther. 2015 Feb;53(2):147-53. doi: 10.5414/CP202197. [Article]
Human Metabolome Database
HMDB0015598
KEGG Drug
D01665
PubChem Compound
444020
PubChem Substance
46504462
ChemSpider
392046
BindingDB
50263044
ChEBI
32300
ChEMBL
CHEMBL476960
ZINC
ZINC000003788703
Therapeutic Targets Database
DAP001104
PharmGKB
PA164752433
PDBe Ligand
VOG
Wikipedia
Voglibose
PDB Entries
6c9x / 6c9z

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceType 2 Diabetes Mellitus1
4CompletedTreatmentImpaired Glucose Tolerance1
4CompletedTreatmentType 2 Diabetes Mellitus3
4Unknown StatusTreatmentInsulin Sensitivity/Resistance / Type 2 Diabetes Mellitus1
3CompletedTreatmentDiabetes Mellitus, Noninsulin Dependent2
3CompletedTreatmentType 2 Diabetes Mellitus2
2CompletedTreatmentType 2 Diabetes Mellitus2
2, 3CompletedTreatmentType 2 Diabetes Mellitus2
Not AvailableCompletedNot AvailableImpaired Glucose Tolerance1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, effervescent
Tablet0.2 mg
Tablet0.3 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility190.0 mg/mLALOGPS
logP-2.3ALOGPS
logP-4.9ChemAxon
logS-0.15ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)7.66ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area153.64 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity59.55 m3·mol-1ChemAxon
Polarizability26.02 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6431
Blood Brain Barrier-0.9478
Caco-2 permeable-0.7878
P-glycoprotein substrateNon-substrate0.6439
P-glycoprotein inhibitor INon-inhibitor0.8759
P-glycoprotein inhibitor IINon-inhibitor0.918
Renal organic cation transporterNon-inhibitor0.873
CYP450 2C9 substrateNon-substrate0.812
CYP450 2D6 substrateNon-substrate0.8224
CYP450 3A4 substrateNon-substrate0.663
CYP450 1A2 substrateNon-inhibitor0.8853
CYP450 2C9 inhibitorNon-inhibitor0.9232
CYP450 2D6 inhibitorNon-inhibitor0.9324
CYP450 2C19 inhibitorNon-inhibitor0.9288
CYP450 3A4 inhibitorNon-inhibitor0.9856
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9737
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9361
BiodegradationNot ready biodegradable0.8142
Rat acute toxicity1.1572 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9395
hERG inhibition (predictor II)Non-inhibitor0.9532
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Maltose alpha-glucosidase 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 dietar...
Gene Name
MGAM
Uniprot ID
O43451
Uniprot Name
Maltase-glucoamylase, intestinal
Molecular Weight
209850.8 Da
References
  1. Satoh N, Shimatsu A, Yamada K, Aizawa-Abe M, Suganami T, Kuzuya H, Ogawa Y: An alpha-glucosidase inhibitor, voglibose, reduces oxidative stress markers and soluble intercellular adhesion molecule 1 in obese type 2 diabetic patients. Metabolism. 2006 Jun;55(6):786-93. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  3. Matsumura M, Monden T, Miyashita Y, Kawagoe Y, Shimizu H, Nakatani Y, Domeki N, Yanagi K, Ikeda S, Kasai K: Effects of changeover from voglibose to acarbose on postprandial triglycerides in type 2 diabetes mellitus patients. Adv Ther. 2009 Jun;26(6):660-6. doi: 10.1007/s12325-009-0040-7. Epub 2009 Jun 30. [Article]
  4. Abe M, Okada K, Maruyama T, Maruyama N, Matsumoto K: Combination therapy with mitiglinide and voglibose improves glycemic control in type 2 diabetic patients on hemodialysis. Expert Opin Pharmacother. 2010 Feb;11(2):169-76. doi: 10.1517/14656560903530683. [Article]
  5. Iwasa M, Kobayashi H, Yasuda S, Kawamura I, Sumi S, Yamada Y, Shiraki T, Yamaki T, Ushikoshi H, Aoyama T, Nishigaki K, Takemura G, Fujiwara T, Fujiwara H, Minatoguchi S: Antidiabetic drug voglibose is protective against ischemia-reperfusion injury through glucagon-like peptide 1 receptors and the phosphoinositide 3-kinase-Akt-endothelial nitric oxide synthase pathway in rabbits. J Cardiovasc Pharmacol. 2010 Jun;55(6):625-34. doi: 10.1097/FJC.0b013e3181dcd240. [Article]
  6. Fujimori Y, Katsuno K, Ojima K, Nakashima I, Nakano S, Ishikawa-Takemura Y, Kusama H, Isaji M: Sergliflozin etabonate, a selective SGLT2 inhibitor, improves glycemic control in streptozotocin-induced diabetic rats and Zucker fatty rats. Eur J Pharmacol. 2009 May 1;609(1-3):148-54. doi: 10.1016/j.ejphar.2009.03.007. Epub 2009 Mar 10. [Article]

Drug created on October 20, 2007 18:23 / Updated on June 19, 2021 00:26