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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
Structure for Voglibose (DB04878)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Post prandial hyperglycemia •••••••••••• •••••• Used in combination to manage Type 1 diabetes mellitus •••••••••••• •••• •••••••• ••••••••••••• ••••••• ••••••• •••••••••••• Treatment of Type 2 diabetes mellitus •••••••••••• •••••• Management of Type 2 diabetes mellitus •••••••••••• ••••••• ••••••• •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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)
Target Actions Organism AMaltase-glucoamylase inhibitorHumans - 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The risk or severity of hypoglycemia can be increased when Acarbose is combined with Voglibose. Acebutolol The therapeutic efficacy of Voglibose can be increased when used in combination with Acebutolol. Acetazolamide The therapeutic efficacy of Voglibose can be increased when used in combination with Acetazolamide. Acetohexamide The risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Voglibose. Acetyl sulfisoxazole The therapeutic efficacy of Voglibose can be increased when used in combination with Acetyl sulfisoxazole. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
- 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]
- 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]
- 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]
- 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]
- External Links
- 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Impaired Glucose Tolerance 1 somestatus stop reason just information to hide Not Available Completed Not Available Type 2 Diabetes Mellitus 3 somestatus stop reason just information to hide Not Available Terminated Prevention Impaired Glucose Tolerance / Myocardial Infarction 1 somestatus stop reason just information to hide Not Available Unknown Status Prevention Coronary Heart Disease (CHD) / Impaired Glucose Tolerance 1 somestatus stop reason just information to hide 4 Completed Basic Science Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, effervescent Tablet 0.2 mg Tablet 0.3 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 190.0 mg/mL ALOGPS logP -2.3 ALOGPS logP -4.9 Chemaxon logS -0.15 ALOGPS pKa (Strongest Acidic) 12.46 Chemaxon pKa (Strongest Basic) 7.66 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 8 Chemaxon Polar Surface Area 153.64 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 59.55 m3·mol-1 Chemaxon Polarizability 26.02 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6431 Blood Brain Barrier - 0.9478 Caco-2 permeable - 0.7878 P-glycoprotein substrate Non-substrate 0.6439 P-glycoprotein inhibitor I Non-inhibitor 0.8759 P-glycoprotein inhibitor II Non-inhibitor 0.918 Renal organic cation transporter Non-inhibitor 0.873 CYP450 2C9 substrate Non-substrate 0.812 CYP450 2D6 substrate Non-substrate 0.8224 CYP450 3A4 substrate Non-substrate 0.663 CYP450 1A2 substrate Non-inhibitor 0.8853 CYP450 2C9 inhibitor Non-inhibitor 0.9232 CYP450 2D6 inhibitor Non-inhibitor 0.9324 CYP450 2C19 inhibitor Non-inhibitor 0.9288 CYP450 3A4 inhibitor Non-inhibitor 0.9856 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9737 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9361 Biodegradation Not ready biodegradable 0.8142 Rat acute toxicity 1.1572 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9395 hERG inhibition (predictor II) Non-inhibitor 0.9532
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-002s-1980000000-33cb901e6f81818552e5 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-32612484dc6456c93ca7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-7d30ee9d6f66bd853cb2 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9160000000-604dff35f55e6ba0a1ed Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0390000000-950f5dca0b5de3075a34 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00dl-9300000000-329323c893be794e4909 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0hk9-1970000000-27645422c44632d83919 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 165.3990405 predictedDarkChem Lite v0.1.0 [M-H]- 165.1044405 predictedDarkChem Lite v0.1.0 [M-H]- 167.04008 predictedDeepCCS 1.0 (2019) [M+H]+ 165.5665405 predictedDarkChem Lite v0.1.0 [M+H]+ 165.2909405 predictedDarkChem Lite v0.1.0 [M+H]+ 169.39809 predictedDeepCCS 1.0 (2019) [M+Na]+ 165.5181405 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.9539405 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.46849 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Alpha-(1,4) exo-glucosidase involved in breakdown of dietary starch oligosaccharides in small intestine. Cleaves the non-reducing alpha-(1,4)-linked glucose residue in linear dextrins with retention of anomeric center stereochemistry (PubMed:12547908, PubMed:18036614, PubMed:18356321, PubMed:22058037, PubMed:27480812). Mainly hydrolyzes short length oligomaltoses having two to seven glucose residues (PubMed:12547908, PubMed:18036614, PubMed:18356321, PubMed:22058037, PubMed:27480812). Can cleave alpha-(1,2), alpha-(1,3) and alpha-(1,6) glycosidic linkages with lower efficiency, whereas beta glycosidic linkages are usually not hydrolyzed (PubMed:27480812)
- Specific Function
- alpha-1,4-glucosidase activity
- Gene Name
- MGAM
- Uniprot ID
- O43451
- Uniprot Name
- Maltase-glucoamylase
- Molecular Weight
- 312020.05 Da
References
- 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]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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]
- 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]
- 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]
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at October 20, 2007 18:23 / Updated at June 19, 2021 00:26