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Identification
NameVoglibose
Accession NumberDB04878
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionVoglibose (INN and USAN) 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. [Wikipedia]
Structure
Thumb
Synonyms
Basen
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BasenTakeda Chemical Industries
GlustatNot Available
VocarbNot Available
VolixRanbaxy labs
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIS77P977AG8
CAS number83480-29-9
WeightAverage: 267.2762
Monoisotopic: 267.131802031
Chemical FormulaC10H21NO7
InChI KeyInChIKey=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[[email protected]]1C[C@](O)(CO)[C@@H](O)[[email protected]](O)[[email protected]]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminocyclitols and derivatives. These are cyclitols with at least one hydroxyl group replace by an amino group.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassCyclic alcohols and derivatives
Direct ParentAminocyclitols and derivatives
Alternative Parents
Substituents
  • Aminocyclitol derivative
  • Cyclohexylamine
  • Cyclohexanol
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Amine
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of diabetes. It is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications.
PharmacodynamicsVoglibose, 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 actionAlpha-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)
Related Articles
AbsorptionSlowly and poorly absorbed
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

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

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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. [PubMed:17509067 ]
  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. [PubMed:16618980 ]
  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. [PubMed:16713439 ]
External Links
ATC CodesA10BF03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AripiprazoleThe therapeutic efficacy of Voglibose can be decreased when used in combination with Aripiprazole.
Arsenic trioxideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Arsenic trioxide.
ArticaineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Articaine.
AsenapineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Asenapine.
AtazanavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Atazanavir.
BendroflumethiazideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Bendroflumethiazide.
BetamethasoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Betamethasone.
BrexpiprazoleThe therapeutic efficacy of Voglibose can be decreased when used in combination with Brexpiprazole.
BumetanideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Bumetanide.
BuserelinThe therapeutic efficacy of Voglibose can be decreased when used in combination with Buserelin.
CeritinibThe therapeutic efficacy of Voglibose can be decreased when used in combination with Ceritinib.
ChlorothiazideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Chlorothiazide.
ChlorpropamideVoglibose may increase the hypoglycemic activities of Chlorpropamide.
ChlorthalidoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Chlorthalidone.
ClozapineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Clozapine.
CorticotropinThe therapeutic efficacy of Voglibose can be decreased when used in combination with Corticotropin.
Cortisone acetateThe therapeutic efficacy of Voglibose can be decreased when used in combination with Cortisone acetate.
Cyproterone acetateThe therapeutic efficacy of Voglibose can be decreased when used in combination with Cyproterone acetate.
DabrafenibThe therapeutic efficacy of Voglibose can be decreased when used in combination with Dabrafenib.
DanazolThe therapeutic efficacy of Voglibose can be decreased when used in combination with Danazol.
DarunavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Darunavir.
DesogestrelThe therapeutic efficacy of Voglibose can be decreased when used in combination with Desogestrel.
DexamethasoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Dexamethasone.
DiazoxideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Diazoxide.
DienogestThe therapeutic efficacy of Voglibose can be decreased when used in combination with Dienogest.
DisopyramideVoglibose may increase the hypoglycemic activities of Disopyramide.
DrospirenoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Drospirenone.
EpinephrineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Epinephrine.
EstradiolThe therapeutic efficacy of Voglibose can be decreased when used in combination with Estradiol.
Estrone sulfateThe therapeutic efficacy of Voglibose can be decreased when used in combination with Estrone sulfate.
Etacrynic acidThe therapeutic efficacy of Voglibose can be decreased when used in combination with Etacrynic acid.
Ethinyl EstradiolThe therapeutic efficacy of Voglibose can be decreased when used in combination with Ethinyl Estradiol.
Ethynodiol diacetateThe therapeutic efficacy of Voglibose can be decreased when used in combination with Ethynodiol diacetate.
EtonogestrelThe therapeutic efficacy of Voglibose can be decreased when used in combination with Etonogestrel.
EverolimusThe therapeutic efficacy of Voglibose can be decreased when used in combination with Everolimus.
FludrocortisoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Fludrocortisone.
FosamprenavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Fosamprenavir.
FurosemideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Furosemide.
GliclazideVoglibose may increase the hypoglycemic activities of Gliclazide.
GlimepirideVoglibose may increase the hypoglycemic activities of Glimepiride.
GlipizideVoglibose may increase the hypoglycemic activities of Glipizide.
GlyburideVoglibose may increase the hypoglycemic activities of Glyburide.
GoserelinThe therapeutic efficacy of Voglibose can be decreased when used in combination with Goserelin.
HistrelinThe therapeutic efficacy of Voglibose can be decreased when used in combination with Histrelin.
HydrochlorothiazideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Hydrochlorothiazide.
HydrocortisoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Hydrocortisone.
HydroflumethiazideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Hydroflumethiazide.
Hydroxyprogesterone caproateThe therapeutic efficacy of Voglibose can be decreased when used in combination with Hydroxyprogesterone caproate.
IloperidoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Iloperidone.
IndapamideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Indapamide.
IndinavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Indinavir.
Insulin AspartVoglibose may increase the hypoglycemic activities of Insulin Aspart.
Insulin DetemirVoglibose may increase the hypoglycemic activities of Insulin Detemir.
Insulin GlargineVoglibose may increase the hypoglycemic activities of Insulin Glargine.
Insulin GlulisineVoglibose may increase the hypoglycemic activities of Insulin Glulisine.
Insulin HumanVoglibose may increase the hypoglycemic activities of Insulin Human.
Insulin LisproVoglibose may increase the hypoglycemic activities of Insulin Lispro.
LanreotideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Lanreotide.
LanreotideVoglibose may increase the hypoglycemic activities of Lanreotide.
LeuprolideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Leuprolide.
LevonorgestrelThe therapeutic efficacy of Voglibose can be decreased when used in combination with Levonorgestrel.
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Voglibose.
LopinavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Lopinavir.
LurasidoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Lurasidone.
MecaserminVoglibose may increase the hypoglycemic activities of Mecasermin.
Medroxyprogesterone acetateThe therapeutic efficacy of Voglibose can be decreased when used in combination with Medroxyprogesterone acetate.
Megestrol acetateThe therapeutic efficacy of Voglibose can be decreased when used in combination with Megestrol acetate.
MestranolThe therapeutic efficacy of Voglibose can be decreased when used in combination with Mestranol.
MethotrimeprazineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Methotrimeprazine.
MethyclothiazideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Methyclothiazide.
MethylprednisoloneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Methylprednisolone.
MetolazoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Metolazone.
MifepristoneVoglibose may increase the hypoglycemic activities of Mifepristone.
NateglinideVoglibose may increase the hypoglycemic activities of Nateglinide.
NelfinavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Nelfinavir.
NiacinThe therapeutic efficacy of Voglibose can be decreased when used in combination with Niacin.
NilotinibThe therapeutic efficacy of Voglibose can be decreased when used in combination with Nilotinib.
NorethisteroneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Norethisterone.
NorgestimateThe therapeutic efficacy of Voglibose can be decreased when used in combination with Norgestimate.
OctreotideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Octreotide.
OctreotideVoglibose may increase the hypoglycemic activities of Octreotide.
OlanzapineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Olanzapine.
PaliperidoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Paliperidone.
PasireotideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Pasireotide.
PasireotideVoglibose may increase the hypoglycemic activities of Pasireotide.
PentamidineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Pentamidine.
PentamidineVoglibose may increase the hypoglycemic activities of Pentamidine.
PiperazineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Piperazine.
PipotiazineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Pipotiazine.
PolythiazideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Polythiazide.
PrednisoloneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Prednisolone.
PrednisoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Prednisone.
ProgesteroneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Progesterone.
QuetiapineThe therapeutic efficacy of Voglibose can be decreased when used in combination with Quetiapine.
QuinethazoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Quinethazone.
QuinineVoglibose may increase the hypoglycemic activities of Quinine.
RepaglinideVoglibose may increase the hypoglycemic activities of Repaglinide.
RisperidoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Risperidone.
RitonavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Ritonavir.
SaquinavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Saquinavir.
SirolimusThe therapeutic efficacy of Voglibose can be decreased when used in combination with Sirolimus.
SulfadiazineVoglibose may increase the hypoglycemic activities of Sulfadiazine.
SulfamethoxazoleVoglibose may increase the hypoglycemic activities of Sulfamethoxazole.
SulfisoxazoleVoglibose may increase the hypoglycemic activities of Sulfisoxazole.
SunitinibVoglibose may increase the hypoglycemic activities of Sunitinib.
TacrolimusThe therapeutic efficacy of Voglibose can be decreased when used in combination with Tacrolimus.
TemsirolimusThe therapeutic efficacy of Voglibose can be decreased when used in combination with Temsirolimus.
TipranavirThe therapeutic efficacy of Voglibose can be decreased when used in combination with Tipranavir.
TolazamideVoglibose may increase the hypoglycemic activities of Tolazamide.
TolbutamideVoglibose may increase the hypoglycemic activities of Tolbutamide.
TorasemideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Torasemide.
TriamcinoloneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Triamcinolone.
TrichlormethiazideThe therapeutic efficacy of Voglibose can be decreased when used in combination with Trichlormethiazide.
TriptorelinThe therapeutic efficacy of Voglibose can be decreased when used in combination with Triptorelin.
VorinostatThe therapeutic efficacy of Voglibose can be decreased when used in combination with Vorinostat.
ZiprasidoneThe therapeutic efficacy of Voglibose can be decreased when used in combination with Ziprasidone.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 dietary oligosaccharides used in food manufacturing.
Gene Name:
MGAM
Uniprot ID:
O43451
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. [PubMed:16713439 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  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. [PubMed:19568704 ]
  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. [PubMed:20025554 ]
  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. [PubMed:20351564 ]
  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. [PubMed:19281809 ]
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Drug created on October 20, 2007 12:23 / Updated on August 17, 2016 12:24