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Voglibose

α-glucosidases inhibitor CAS# 83480-29-9

Voglibose

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Chemical structure

Voglibose

3D structure

Chemical Properties of Voglibose

Cas No. 83480-29-9 SDF Download SDF
PubChem ID 444020 Appearance Powder
Formula C10H21NO7 M.Wt 267.28
Type of Compound N/A Storage Desiccate at -20°C
Solubility H2O : 100 mg/mL (374.14 mM; Need ultrasonic)
DMSO : 100 mg/mL (374.14 mM; Need ultrasonic)
Chemical Name (1S,2S,3R,4S,5S)-5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol
SMILES C1C(C(C(C(C1(CO)O)O)O)O)NC(CO)CO
Standard InChIKey FZNCGRZWXLXZSZ-CIQUZCHMSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Voglibose

DescriptionOrally active α-glucosidase inhibitor (IC50 values are 3.9 and 6.4 nM at sucrase and maltase respectively). Increases glucagon-like peptide 1 (GLP-1) secretion and decreases food consumption in ob/ob mice, and reduces plasma concentrations of glucose, triglycerides and insulin in Wistar fatty rats. Exhibits antidiabetic and antiobesity activity in vivo.

Voglibose Dilution Calculator

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Preparing Stock Solutions of Voglibose

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.7414 mL 18.707 mL 37.4139 mL 74.8279 mL 93.5349 mL
5 mM 0.7483 mL 3.7414 mL 7.4828 mL 14.9656 mL 18.707 mL
10 mM 0.3741 mL 1.8707 mL 3.7414 mL 7.4828 mL 9.3535 mL
50 mM 0.0748 mL 0.3741 mL 0.7483 mL 1.4966 mL 1.8707 mL
100 mM 0.0374 mL 0.1871 mL 0.3741 mL 0.7483 mL 0.9353 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Voglibose

Voglibose is an N-substituted derivative of valiolamine, excellent inhibitory activity against α-glucosidases and its action against hyperglycemia and various disorders caused by hyperglycemia.

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References on Voglibose

Cross-Over Study Comparing Postprandial Glycemic Increase After Addition of a Fixed-Dose Mitiglinide/Voglibose Combination or a Dipeptidyl Peptidase-4 Inhibitor to Basal Insulin Therapy in Patients with Type 2 Diabetes Mellitus.[Pubmed:28242866]

Med Sci Monit Basic Res. 2017 Feb 28;23:36-44.

BACKGROUND Although the efficacy of combination therapy consisting of basal insulin and oral hypoglycemic agents (OHAs) has been shown, which OHAs are the most efficient remains unclear. MATERIAL AND METHODS Five patients with type 2 diabetes were enrolled and treated with insulin degludec and metformin as a basal therapy. The patients were randomized in a cross-over fashion to receive a combination of mitiglinide (10 mg) and Voglibose (0.2 mg) (M+V) 3 times daily or linagliptin (5 mg) (L) once daily for 8 weeks. After 8 weeks, 2 kinds of meal tolerance tests were performed as breakfast on 2 consecutive days. The first breakfast contained 460 kcal (carbohydrates, 49.1%; protein, 15.7%; fat, 35.2%), while the second contained 462 kcal (carbohydrates, 37.2%; protein, 19.6%; fat, 43.2%). Self-monitoring blood glucose levels were measured at 0, 30, 60, and 120 min after the meal tests, and the increase in the postprandial area under the curve (AUC)0-120 min was determined. The HbA1c, glycated albumin, and 1,5-anhydroglucitol (AG) levels were measured, and continuous glucose monitoring was performed. RESULTS The increase in the postprandial AUC0-120 min was significantly smaller in the M+V group than in the L group after both meals. The 24-h average, 24-h standard deviations, 24-h AUC, and mean amplitude of glycemic excursion (MAGE) were similar for both groups and after both meals. The change in 1,5-AG was higher in the M+V group than in the L group. CONCLUSIONS The combination of M+V with basal therapy improved postprandial glucose excursion more effectively than L in T2DM patients.

Reappraisal and perspectives of clinical drug-drug interaction potential of alpha-glucosidase inhibitors such as acarbose, voglibose and miglitol in the treatment of type 2 diabetes mellitus.[Pubmed:28010166]

Xenobiotica. 2018 Jan;48(1):89-108.

1. Amidst the new strategies being developed for the management of type 2 diabetes mellitus (T2DM) with both established and newer therapies, alpha glucosidase inhibitors (AGIs) have found a place in several treatment protocols. 2. The objectives of the review were: (a) to compile and evaluate the various clinical pharmacokinetic drug interaction data for AGIs such as acarbose, miglitol and Voglibose; (b) provide perspectives on the drug interaction data since it encompasses coadministered drugs in several key areas of comorbidity with T2DM. 3. Critical evaluation of the interaction data suggested that the absorption and bioavailability of many coadministered drugs were not meaningfully affected from a clinical perspective. Therefore, on the basis of the current appraisal, none of the AGIs showed an alarming and/or overwhelming trend of interaction potential with several coadministered drugs. Hence, dosage adjustment is not warranted in the use of AGIs in T2DM patients in situations of comorbidity. 4. The newly evolving fixed dose combination strategies with AGIs need to be carefully evaluated to ensure that the absorption and bioavailability of the added drug are not impaired due to concomitant food ingestion.

Effects of linagliptin monotherapy compared with voglibose on postprandial blood glucose responses in Japanese patients with type 2 diabetes: Linagliptin Study of Effects on Postprandial blood glucose (L-STEP).[Pubmed:27710821]

Diabetes Res Clin Pract. 2016 Nov;121:146-156.

AIMS: To compare the efficacy on glycemic parameters between a 12-week administration of once-daily linagliptin and thrice-daily Voglibose in Japanese patients with type 2 diabetes. METHODS: In a multi-center, randomized, parallel-group study, 382 patients with diabetes were randomized to the linagliptin group (n=192) or the Voglibose group (n=190). A meal tolerance test was performed at weeks 0 and 12. Primary outcomes were the change from baseline to week 12 in serum glucose levels at 2h during the meal tolerance test, HbA1c levels, and serum fasting glucose levels, which were compared between the 2 groups. RESULTS: Whereas changes in serum glucose levels at 2h during the meal tolerance test did not differ between the groups, the mean change in HbA1c levels from baseline to week 12 in the linagliptin group (-0.5+/-0.5% [-5.1+/-5.4mmol/mol]) was significantly larger than in the Voglibose group (-0.2+/-0.5% [-2.7+/-5.4mmol/mol]). In addition, there was significant difference in changes in serum fasting glucose levels (-0.51+/-0.95mmol/L in the linagliptin group vs. -0.18+/-0.92mmol/L in the Voglibose group, P<0.001). The incidences of hypoglycemia, serious adverse events (AEs), and discontinuations due to AEs were low and similar in both groups. However, gastrointestinal AEs were significantly lower in the linagliptin group (1.05% vs. 5.85%; P=0.01). CONCLUSIONS: These data suggested that linagliptin monotherapy had a stronger glucose-lowering effect than Voglibose monotherapy with respect to HbA1c and serum fasting glucose levels, but not serum glucose levels 2h after the start of the meal tolerance test.

Comparison Between Effectiveness of 100 mg/day Sitagliptin and a Switch to Mitiglinide Calcium Hydrate/Voglibose from 50 mg/day Sitagliptin in Patients with Type 2 Diabetes.[Pubmed:28331117]

J UOEH. 2017;39(1):1-9.

We analyzed the effects of 100 mg/day sitagliptin and a switch to mitiglinide calcium hydrate/Voglibose compound tablets (MIT/VOG) in patients with type 2 diabetes mellitus (T2DM) treated with 50 mg/day sitagliptin. Five patients with T2DM treated with 50 mg/day sitagliptin and hemoglobin A1c (HbA1c) of >/=6.5% were switched to MIT/VOG, or the dose of sitagliptin was increased to 100 mg/day. The effects of the changes in therapy were compared in a crossover fashion by continuous glucose monitoring. The primary endpoint was mean amplitude of glycemic excursions (MAGE), and the secondary end points were 24-hour mean blood glucose level and mean blood glucose level from 0:00 a.m. to 7:00 a.m. and from 7:00 a.m. to 0:00 a.m., percentage of time with blood glucose level of >/=200 mg/dl and <70 mg/dl, maximum and minimum blood glucose levels, and increases in postprandial blood glucose levels. MAGE was significantly lower with MIT/VOG (P = 0.016), whereas mean blood glucose levels were lower between 0:00 a.m. and 7:00 a.m. with 100 mg/day sitagliptin. The percentage of time with blood glucose level >/=200 mg/dl was significantly shorter with MIT/VOG (P = 0.041). The maximum blood glucose level was significantly lower with MIT/VOG (P = 0.043), and the minimum was significantly lower with 100 mg/day sitagliptin (P = 0.043). Blood glucose levels after dinner and mean increases in postprandial blood glucose levels were significantly lower with MIT/VOG (P = 0.090 and P = 0.045 respectively). In patients with T2DM, treatment with MIT/VOG improves MAGE and postprandial hyperglycemia and 100 mg/day sitagliptin lowers early morning glucose levels. This trial was registered with the University Hospital Medical Information Network (UMIN) (No. UMIN R000008274).

Alpha-glucosidase inhibition assay in an enzyme-immobilized amino-microplate.[Pubmed:19359799]

Anal Sci. 2009 Apr;25(4):559-62.

Alpha-glucosidase (AGH) from the small intestine of rat was immobilized onto a glutaraldehyde (GA) activated NH(2)-96 well microplate to establish a convenient and rapid AGH inhibition assay system. After AGH immobilization, remaining GA groups were blocked by beta-alanine to induce a negative charge on the surface of the well. The AGH-plate showed an enzyme activity of 444 nU/well under an assayed condition at 37 degrees C for 2 h using 0.3 mM 4-methylumbelliferyl-alpha-D-glucopyranoside as a fluorogenic substrate. Inhibitory powers of Voglibose and acarbose as therapeutic AGH inhibitors were successfully evaluated to have IC(50) values of 13 and 114 nM, respectively.

Chronic administration of voglibose, an alpha-glucosidase inhibitor, increases active glucagon-like peptide-1 levels by increasing its secretion and decreasing dipeptidyl peptidase-4 activity in ob/ob mice.[Pubmed:19208898]

J Pharmacol Exp Ther. 2009 May;329(2):669-76.

Administration of an alpha-glucosidase inhibitor, Voglibose, increases the secretion of glucagon-like peptide (GLP)-1, a key modulator of pancreatic islet hormone secretion and glucose homeostasis. In the present study, novel mechanisms by which Voglibose increases active GLP-1 circulation were evaluated. Voglibose (0.001 and 0.005%) was administered in the diet to ob/ob mice for 1 day or 3 to 4 weeks to determine effects on incretin profiles and plasma activity of dipeptidyl peptidase-4 (DPP-4), an enzyme responsible for GLP-1 degradation. Voglibose showed no direct inhibitory effect against DPP-4 in vitro (DPP-4 inhibitor alogliptin, IC(50) < 10 nM). Likewise, 1-day treatment with Voglibose did not change plasma DPP-4 activity; however, it increased plasma active GLP-1 by 1.6- to 3.4-fold. After chronic treatment, Voglibose stimulated GLP-1 secretion, as evidenced by the 1.3- to 1.5-fold increase in plasma active plus inactive amidated GLP-1 levels. Plasma DPP-4 activity was decreased unexpectedly by 40 to 51%, resulting from reduced plasma DPP-4 concentrations in Voglibose-treated mice. Voglibose increased GLP-1 content by 1.5- to 1.6-fold and 1.4- to 1.6-fold in the lower intestine and colon, respectively. The increased GLP-1 content in the colon was associated with elevated expression of gut glucagon gene. Chronic treatment with Voglibose resulted in 1.9- to 4.1-fold increase in active GLP-1 circulation, which was higher than 1-day treatment. A similar treatment with pioglitazone (0.03%), an insulin sensitizer, did not affect plasma DPP-4 activity or GLP-1 levels. These results suggest that increased GLP-1 secretion, decreased DPP-4 activity, and increased gut GLP-1 content may have contributed to increased active GLP-1 circulation after chronic treatment with Voglibose in a glucose control-independent manner in ob/ob mice.

Effect of an intestinal disaccharidase inhibitor (AO-128) on obesity and diabetes.[Pubmed:1728846]

Am J Clin Nutr. 1992 Jan;55(1 Suppl):314S-317S.

A new disaccharidase inhibitor, AO-128, showed 190-3900-fold more potent inhibition of purified rat small intestine sucrase-isomaltase (S-1) complex and 23-33-fold more potent inhibition of semipurified porcine small intestine disaccharidases than acarbose. AO-128 suppressed elevation of the blood glucose concentration after oral sucrose, maltose, and starch, but not after oral glucose, fructose, and lactose. The chronic addition of AO-128 to the diet produced antiobesity and antidiabetic actions in obese and/or diabetic animals. Undesirable side effects, such as diarrhea and soft feces, were observed only for the first 5-7 d and suppression of intestinal disaccharidase activities was observed even at the end of the experiment, suggesting that the suppressive or delaying effect of AO-128 on elevation of the postprandial blood glucose concentrations is involved in reduction in body weight gain and prevention and/or amelioration of the diabetic state. Thus, AO-128 is useful as an adjunct to the dietary management of obesity and diabetes.

Description

Voglibose is an N-substituted derivative of valiolamine, excellent inhibitory activity against α-glucosidases and its action against hyperglycemia and various disorders caused by hyperglycemia.

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