(1S,2S,3R,4S,5S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol

• ChemBase ID: 4394
• Molecular Formular: C10H21NO7
• Molecular Mass: 267.27624
• Monoisotopic Mass: 267.13180202
• SMILES: O[C@@]1(C[C@H](NC(CO)CO)[C@H](O)[C@@H](O)[C@@H]1O)CO
• Canonical SMILES: OCC(N[C@H]1C[C@](O)(CO)[C@H]([C@@H]([C@H]1O)O)O)CO
• 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
• InChIKey: FZNCGRZWXLXZSZ-CIQUZCHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3R,4S,5S)-5-[(1,3-dihydroxypropan-2-yl)amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
• IUPAC Traditional name: voglibose
• Brand Name: Basen (Takeda Chemical Industries); Volix (Ranbaxy labs); Glustat; Vocarb; Basen
• Synonyms: 3,4-Dideoxy-4-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-D-epi-inositol; N-(1,3-Dihydroxyprop-2-yl)valiolamine; Voglibose; voglibose; Voglibose

Database IDs

• CAS Number: 83480-29-9
• MDL Number: MFCD00865496
• PubChem SID: 160967826; 46504462
• PubChem CID: 444020

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.455839
• H Acceptors: 8
• H Donor: 8
• LogD (pH = 5.5): -6.9796877
• LogD (pH = 7.4): -5.301458
• Log P: -4.8527865
• Molar Refractivity: 59.5467 cm^3
• Polarizability: 24.53386 Å^3
• Polar Surface Area: 153.64 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.34
• LOG S: -0.15
• Solubility (Water): 1.90e+02 g/l

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (TLC)
• Empirical Formula (Hill Notation): C10H21NO7

DETAILS

DrugBank - DB04878

• Drug Groups: approved; investigational
• 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]
• 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: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Little metabolism occurs and no metabolites have as yet been identified.
• Absorption: Slowly and poorly absorbed
• 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. [Pubmed] ; 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] ; 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: Wikipedia

Sigma Aldrich - 50359

Application
Voglibose is an α-glucosidase inhibitor, similar to acarbose and miglitol, used for lowering post-prandial hyperglycemia (PPHG) in people with diabetes mellitus. Voglibose is used to study it benefits as a protectant against ischemia-reperfusion injury through glucagon-like peptide 1 receptors and the phosphoinositide 3-kinase-Akt-endothelial nitric oxide synthase pathway.

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. Pubmed
• 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
• 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