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Identification
Name Voglibose
Accession Number DB04878
Type small molecule
Groups approved
Description

Voglibose (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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Basen
Basen (Takeda Chemical Industries)
Glustat
Vocarb
Volix (Ranbaxy labs)
Brand mixtures Not Available
Categories
  • Hypoglycemic Agents
CAS number 83480-29-9
Weight Average: 267.2762
Monoisotopic: 267.131802031
Chemical Formula C10H21NO7
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Glycerol and Derivatives
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Aliphatic and Aryl Amines
  • Alcohols and Polyols
  • Amino Alcohols
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.
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)
Absorption Slowly and poorly absorbed
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 Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 1.90e+02 g/l 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 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 59.55 ChemAxon
polarizability 26.02 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
  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
  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
External Links
Resource Link
KEGG Drug D01665 Link_out
PubChem Compound 444020 Link_out
PubChem Substance 46504462 Link_out
ChemSpider 392046 Link_out
BindingDB 50263044 Link_out
Therapeutic Targets Database DAP001104 Link_out
PharmGKB PA164752433 Link_out
Wikipedia http://en.wikipedia.org/wiki/Voglibose Link_out
ATC Codes
  • A10BF03
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Maltase-glucoamylase, intestinal

Pharmacological action: yes
Actions: inhibitor

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

Organism class: human
UniProt ID: O43451 Link_out
Gene: MGAM Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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. Epub 2009 Jun 30. Pubmed
  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. Pubmed
  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. Pubmed
  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. Epub 2009 Mar 10. Pubmed
Comments
Drug created on October 20, 2007 12:23 / Updated on February 08, 2013 16:23