Voglibose

Base Information

• Chemical Name: Voglibose
• CAS No.: 83480-29-9
• Deprecated CAS: 112653-29-9
• Molecular Formula: C10H21NO7
• Molecular Weight: 267.279
• UNII: S77P977AG8
• DSSTox Substance ID: DTXSID2021442,DTXSID501031239
• Nikkaji Number: J556.821H
• Wikipedia: Voglibose
• Wikidata: Q7939403
• NCI Thesaurus Code: C95221
• Pharos Ligand ID: PUUPCSW6697X
• Metabolomics Workbench ID: 43638
• ChEMBL ID: CHEMBL476960
• Mol file: 83480-29-9.mol

Synonyms:3,4-dideoxy-4-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-2-C-(hydroxymethyl)-D-epi-inositol;Basen;N-(1,3-dihydroxy-2-propyl)valiolamine;voglibose

Chemical Property of Voglibose

Chemical Property:

• Appearance/Colour: Colourless crystalline solid
• Vapor Pressure: 5.37E-17mmHg at 25°C
• Melting Point: 162-163 °C
• Refractive Index: 1.635
• Boiling Point: 601.9 °C at 760 mmHg
• PKA: 13.26±0.70(Predicted)
• Flash Point: 274.1 °C
• PSA: 153.64000
• Density: 1.58 g/cm³
• LogP: -4.10150
• Storage Temp.: Store at -20°C
• Solubility.: DMSO (Slightly), Methanol (Very Slightly, Heated), Water (Sparingly, Sonicated)
• XLogP3: -4.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 267.13180201
• Heavy Atom Count: 18
• Complexity: 263

Purity/Quality:

99%min ^*data from raw suppliers

Voglibose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1(CO)O)O)O)O)NC(CO)CO
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]([C@]1(CO)O)O)O)O)NC(CO)CO
• Recent ClinicalTrials: Glycaemic & Cardiovascular Treatment Outcomes of Voglibose Vs Glibenclamide Added to Metformin in T2DM Patients
• Recent NIPH Clinical Trials: The effect of lowering blood glucose regarding SGLT2 inhibitor in type 1 diabetes mellitus
• Uses: 1. It is used for treating diabetes. 2. Anti-diabetic drug. An α-Glucosidase inhibitor used as an antidiabetic. For the treatment of diabetes. It is specifically used for lowering post-prandial blood glucose levels thereby reducing the risk of macrovascular complications. An alpha-Glucosidase inhibitor used as an antidiabetic 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.
• Description: Voglibose was introduced in Japan for the treatment of postprandial hyperglycemia in diabetic patients. As an orally active α-D-glucosidase inhibitor, it is effective in decreasing the release of glucose from carbohydrate ingestion and slowing the increase of postprandial blood glucose levels, as demonstrated in animals and humans following sucrose and starch loading. In addlion, voglibose was reported to have prophylactic effect in genetically obese Wistar rats, maintaining low plasma levels of glucose, triglyceride and insulin, indicating a potential usefulness for the management of other carbohydrate-dependent metabolic disorders such as obesity. Voglibose is much more potent and has fewer side effects than acarbose, another agent in its class.
• Therapeutic Function: Antidiabetic, Antiobesity

Technology Process of Voglibose

There total 21 articles about Voglibose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.5%

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol (115250-39-0) → voglibose (83480-29-9,112653-29-9)

Guidance literature:

With formic acid; palladium 10% on activated carbon; hydrogen; In methanol; at 35 ℃; for 18h; Temperature; Time;

Reference yield: 85.0%

dihydroxyacetone (96-26-4,26776-70-5) + (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane (83465-22-9) → voglibose (83480-29-9,112653-29-9)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In N,N-dimethyl-formamide; at 60 ℃; for 24h;

Reference yield: 85.0%

C42H41NO13 → voglibose (83480-29-9,112653-29-9)

Guidance literature:

In water; for 24h; Reflux;

upstream raw materials:

dihydroxyacetone

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

(1S)-(1(OH),2,4,5/1,3)-2,3,4-tri-O-benzyl-5-<<2-hydroxy-1-(hydroxymethyl)ethyl>amino>-1-C-<(benzyloxy)methyl>-1,2,3,4-cyclohexanetetrol

(1S)-(1(OH),2,4/1,3)-2,3,4-Tri-O-benzyl-1-C-<(benzyloxy)methyl>-5-oxo-1,2,3,4-cyclohexanetetrol

Downstream raw materials:

(R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)butanoyl]-3-(t-butoxymethyl)piperazin-2-one(tartrate)

Refernces

• 1、 -. "Method for preparing voglibose and corresponding intermediate". Paragraph 0152-0154. . Retrieved 2019/01/23.
• 2、 -. "Preparation method for voglibose". Paragraph 0032; 0033. . Retrieved 2018/11/27.