2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol
Voglibose
CAS: 83480-29-9
Molecular Formula: C10H21NO7
2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol - Names and Identifiers
| Name | Voglibose |
| Synonyms | Jumeal Beigrace Voglibose Voglistat N-(1,3-Dihydroxyprop-2-yl)valiolamine 3,4-Dideoxy-4-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-2-D-epi-inositol 5-(1,3-dihydroxypropan-2-ylamino)-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol 2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol epi-Inositol, 2,3-dideoxy-2-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-4-C-(hydroxymethyl)- 3,4-DIDEOXY-4-[[2-HYDROXY-1-(HYDROXYMETHYL)ETHYL]AMINO]-2-C-(HYDROXYMETHYL)-D-EPINOSITOL 3,4-DIDEOXY-4-[[2-HYDROXY-1-(HYDROXYMETHYL)ETHYL]AMINO]-2-C-(HYDROXYMETHYL)-D-EPIINOSITOL (2S,3R,5S)-5-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-1-(hydroxymethyl)cyclohexane-1,2,3,4-tetrol |
| CAS | 83480-29-9 |
| EINECS | 1312995-182-4 |
| InChI | InChI=1/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 |
2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol - Physico-chemical Properties
| Molecular Formula | C10H21NO7 |
| Molar Mass | 267.28 |
| Density | 1.58±0.1 g/cm3(Predicted) |
| Melting Point | 162-163°C |
| Boling Point | 601.9±55.0 °C(Predicted) |
| Specific Rotation(α) | D25 +26.2° (c = 1 in water) |
| Flash Point | 274.1°C |
| Solubility | H2O : 100 mg/mL (374.14 mM; Need ultrasonic);DMSO : 100 mg/mL (374.14 mM; Need ultraso |
| Vapor Presure | 5.37E-17mmHg at 25°C |
| Appearance | White to off-white crystalline powder |
| Color | White to Off-White |
| Merck | 14,10029 |
| pKa | 13.26±0.70(Predicted) |
| Storage Condition | -20°C |
| Refractive Index | 1.635 |
| MDL | MFCD00865496 |
| Use | For the treatment of diabetes |
| In vitro study | Voglibose can inhibit intestinal alpha-glucosidase enzymes, which are responsible for the digestion of disaccharides such as maltose and sucrose, including maltase and sucrase. The K I value of Voglibose for sucrase and maltase is less than the K m value of sucrose and maltose about 10 |
| In vivo study | Voglibose (0.2 mg/kg) completely inhibited the insulin response to sucrose and reduced the carbohydrate-induced increase in blood glucose in mice. Voglibose (0.2 mg/kg) acts on both normal and neonatal strep tozotocin-induced diabetic rats to reduce the carbohydrate-induced increase in blood glucose without causing persistent hypoglycemia. After 3 weeks of treatment with Voglibose (0.001%) in pre-diabetic db / db mice, there was a GLP-1 increase in secretion (Voglibose alone, 1.6-fold; Alogliptin plus Voglibose,1.5-fold), while reducing plasma insulinotropic polypeptide (GIP)(Voglibose alone, 30%; Alogliptin plus voglibose, 29%). Treatment of pre-diabetic db / db mice with Voglibose (0.001%) increased plasma insulin 1.8-fold, reducing plasma DPP-4 activity by 15% and plasma glucagon by 8%. Voglibose (0.001% and 0.005%) acts on ob/ob mice to stimulate secretion in GLP-1, adding to the standard inactive amidated GLP-1, increasing plasma activity by 1.3 to 1.5 fold. Action of Voglibose (0.001% and 0.005%) on ob/ob mice unexpectedly reduced plasma DPP-4 activity by 40% to 51%, resulting from a decrease in plasma DPP-4 concentration. Voglibose (0.001% and 0.005%) acts on ob/ob mice to increase 1.5-to 1.6-fold the content of GLP-1, decreasing 1.4-to 1.6-fold in the small intestine and large intestine, respectively. |
2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| RTECS | NM7524600 |
2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol - Reference
| Reference Show more | 1. Hou, Xiaorong, et al. "Development of an immobilized liposome chromatography method for screening and characterizing α-glucosidase-binding compounds." Journal of Chromatography B 1148 (2020): 122097.https://doi.org/10.1016/j.jchromb.2020.122097 2. [IF=3.205] Xiaorong Hou et al."Development of an immobilized liposome chromatography method for screening and characterizing α-glucosidase-binding compounds."J Chromatogr B. 2020 Jul;1148:122097 |
2,3-Dideoxy-2-[[2-hydroxy-1-(hydroxymethyl)ethyl]amino]-4-C-(hydroxymethyl)-epi-inositol - Reference Information
| Oral hypoglycemic drug | Voglibose is an oral hypoglycemic drug that can improve diabetes Postprandial hyperglycemia, successfully developed by Takeda Company of Japan, belongs to α-glucosidase inhibitor (a drug that delays the absorption of carbohydrates in the intestine to achieve hypoglycemic effect ), the mechanism of action is to inhibit the disaccharide hydrolase (α-glucosidase) that breaks down disaccharides into monosaccharides in the intestine, thus delaying the digestion and absorption of sugar, thereby improving postprandial hyperglycemia. Healthy adults were given after sucrose load, the exhaled hydrogen was measured, and the results confirmed that the drug has an inhibitory effect on blood sugar increase under clinical dosage. When normal rats are given orally, this product inhibits the increase of blood sugar after loading with starch, maltose and sucrose, but has no inhibitory effect on the increase of blood sugar after loading with glucose, fructose and lactose. Studies on the mechanism of action of in vitro experiments show that this product has a strong inhibitory effect on maltase and sucrase obtained from the small intestine of pigs and rats; on the other hand, It has a weak inhibitory effect on α-pancreatic amylase in pigs and rats, but has no inhibitory effect on β-glucosidase. The disaccharide hydrolase of the sucrase-isomaltase complex of the rat small intestine is a competitive inhibition. It is understood that Voglibose has a wide range of applications, not only for middle-aged and elderly diabetic patients, but also for refractory type 2 diabetic patients, patients with secondary failure of sulfonylureas, and diabetic patients with hyperlipidemia, Diabetes patients with heart and brain blood tube disease, and patients with hyperinsulinemia have significant effects. Since this product does not stimulate the secretion of insulin, it can reduce the harmful effects of postprandial hyperinsulinemia, reduce insulin resistance, and is beneficial to the prevention and treatment of metabolic syndrome such as cardiovascular complications. |
| indications | voglibose, as a second-generation α-glycosidase inhibitor, mainly selectively inhibits sucrase and maltase, and its inhibitory activity on these two enzymes is much higher than that of acarbose. Because it does not affect amylase, the starch in food is converted into disaccharide in the small intestine, and the starch entering the large intestine is very small, so there are fewer gastrointestinal reactions such as abdominal distension and increased exhaust. Voglibose is rarely absorbed by prototype drugs, and more than 98% are metabolized in the intestine and excreted in feces, so it can be used in patients with mild to moderate liver dysfunction. Voglibose tablets are the first choice and first-line medication for diabetic patients with high blood sugar after meals. They are suitable for all age groups and can be arbitrarily matched with other non-similar hypoglycemic drugs, such as insulin, secretagogues, etc. It is more suitable for patients with difficult diet control. Single-quality sugar control. Any dose will not cause hypoglycemia due to drug factors. When combined with insulin and secretagogues, attention should be paid to the risk of hypoglycemia. It is recommended to start taking it at a small dose. |
| side effects | the mechanism of side effects of oral hypoglycemic drugs is generally that after unabsorbed sugar enters the large intestine, under the action of bacteria, it is fermented to produce carbon dioxide, hydrogen and organic acids. At the same time, due to increased intestinal osmotic pressure and water retention, there is increased exhaust, abdominal distension and diarrhea. Since voglibose can selectively inhibit disaccharide hydrolase in the intestine, delay the rapid digestion and absorption of sugars in the upper part of the small intestine, and reduce the amount of sugar entering the large intestine, the incidence of adverse reactions is low . It is known to have the following adverse reactions: 1) digestive system: diarrhea, soft stools, abdominal ringing, abdominal pain, constipation, loss of appetite, nausea, vomiting, heartburn (incidence rate below 0.1-5%), stomatitis, thirst, abnormal taste, intestinal wall cystic pneumocytosis (0.1% below ) 2) allergic symptoms: rash, pruritus, photosensitivity (incidence below 0.1%) 3) Liver: GOT, GPT, LDH, γ-GTP, ALP (incidence below 0.1%) 4) Mental nervous system: headache, dizziness, faltering, drowsiness (incidence below 0.1%) 5) Blood system: anemia (incidence rate below 0.1-5%), thrombocytopenia (below 0.1%) 6) others: paralysis, facial edema, hazy eyes, fever, tiredness, fatigue, hyperkalemia, increased serum amylase, decreased high density lipoprotein, sweating, hair removal (incidence rate below 0.1%). |
| biological activity | Voglibose (AO 128) is an N-substituted Jinglianolamine derivative, which has excellent inhibitory activity against α glucosidase, and also has anti-hyperglycemia and various diseases caused by hyperglycemia. |
| target | TargetValue α-glucosidases |
| Target | Value |
| in vitro studies | Voglibose can inhibit intestinal α-glucosidase, which is responsible for the digestion of disaccharides, such as maltose and sucrose, including maltase and sucrase. The K I values of Voglibose for sucrase and maltase are respectively less than the K m values of sucrose and maltose by about 10 |
| in vivo studies | Voglibose (0.2 mg/kg) acts on mice to completely inhibit the insulin response of sucrose and reduce the increase of carbohydrate-induced blood sugar. Voglibose (0.2 mg/kg) acts on normal and newborn streptozotocin-induced diabetic rats to reduce carbohydrate-induced increase in blood sugar without causing persistent hypoglycemia. After 3 weeks of Voglibose (0.001%) treatment of prediabetic db / db mice, it increased GLP-1 secretion (Voglibose alone, 1.6 times; Alogliptin plus Voglibose,1.5 times), while reducing plasma insulinotropic polypeptide (GIP)(Voglibose alone, 30%; Alogliptin plus voglibose, 29%). Voglibose (0.001%) treatment of prediabetic db / db mice increased plasma insulin by 1.8 times, decreased plasma DPP-4 activity by 15% and plasma glucagon by 8%. Voglibose (0.001% and 0.005%) acted on ob/ob mice to stimulate the secretion of GLP-1. When added to the standard inactive amidation GLP-1, the activity in plasma increased by 1.3 to 1.5 times. Voglibose (0.001% and 0.005%) acts on ob/ob mice to accidentally reduce the activity of plasma DPP-4 40% to 51%, which is caused by reducing the concentration of plasma DPP-4. Voglibose (0.001% and 0.005%) acted on ob/ob mice to increase the GLP-1 content by 1.5-to 1.6-fold, and decreased by 1.4 to 1.6-fold in the small intestine and large intestine respectively. |
| use | used to treat diabetes antidiabetic drugs |
Last Update：2024-04-10 22:43:14
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