metformin
metformin
CAS: 657-24-9
Molecular Formula: C4H11N5
metformin - Names and Identifiers
| Name | metformin |
| Synonyms | dmgg la6023 melbin flumamine gliguanid metformin haurymelin dimethylbiguanide 1,1-dimethyl-biguanid 1,1-dimethylbiguanide |
| CAS | 657-24-9 |
| EINECS | 211-517-8 |
| InChI | InChI=1/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8) |
metformin - Physico-chemical Properties
| Molecular Formula | C4H11N5 |
| Molar Mass | 129.16 |
| Density | 1.0743 (rough estimate) |
| Melting Point | 199-200 °C |
| Boling Point | 229.23°C (rough estimate) |
| Solubility | Acetonitrile (Slightly), Aqueous Acid (Slightly), Dichloromethane (Slightly), DM |
| Appearance | Solid |
| Color | White to Light Brown |
| pKa | pKa 2.8(H2O,t =32) (Uncertain) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.5760 (estimate) |
metformin - Risk and Safety
| Toxicity | LD50 oral in mouse: 1450mg/kg |
metformin - Reference
| Reference Show more | 1. Cai, Wu-Dan, et al. "Hypoglycemic benefit and potential mechanism of a polysaccharide from Hericium erinaceus in streptozotoxin-induced diabetic rats." Process Biochemistry 88 (2020): 180-188.https://doi.org/10.1016/j.procbio.2019.09.035 2. Li, Yan, et al. "Dezhou donkey (Equus asinus) milk a potential treatment strategy for type 2 diabetes." Journal of ethnopharmacology 246 (2020): 112221.https://doi.org/10.1016/j.jep.2019.112221 3. [IF=3.267] Ping Zhao et al."Ethanolic Extract of Folium Sennae Mediates the Glucose Uptake of L6 Cells by GLUT4 and Ca2+."Molecules. 2018 Nov;23(11):2934 4. [IF=3.225] Wenhao Xu et al."Mechanochemical preparation of kaempferol intermolecular complexes for enhancing the solubility and bioavailability."Drug Dev Ind Pharm. 2018;44(12):1924-1932 5. [IF=2.371] Liu Changhe et al."Metformin Regulates the Expression of SK2 and SK3 in the Atria of Rats With Type 2 Diabetes Mellitus Through the NOX4/p38MAPK Signaling Pathway."J Cardiovasc Pharm. 2018 Nov;72(5):205-213 6. [IF=5.396] Yao-Yao Wang et al."Antidiabetic activity of a polysaccharide-protein complex from Asian Clam (Corbicula fluminea) in streptozotoxin-induced diabetic rats and its underlying mechanism."Food Funct. 2019 Sep;10(9):5574-5586 7. [IF=5.279] Mengdi Chen et al."Novel Umami Peptide IPIPATKT with Dual Dipeptidyl Peptidase-IV and Angiotensin I-Converting Enzyme Inhibitory Activities."J Agr Food Chem. 2021;69(19):5463–5470 8. [IF=4.818] Yong Zhang et al."Mangiferin Ameliorates HFD-Induced NAFLD through Regulation of the AMPK and NLRP3 Inflammasome Signal Pathways."J Immunol Res. 2021;2021:4084566 9. [IF=4.225] Zhang Yi et al."Edgeworthia gardneri (Wall.) Meisn. Water Extract Ameliorates Palmitate Induced Insulin Resistance by Regulating IRS1/GSK3β/FoxO1 Signaling Pathway in Human HepG2 Hepatocytes."Front Pharmacol. 2020 Jan;0:1666 10. [IF=4.171] Lin Han et al."Activation of AMPK/Sirt3 pathway by phloretin reduces mitochondrial ROS in vascular endothelium by increasing the activity of MnSOD via deacetylation."Food Funct. 2020 Apr;11(4):3073-3083 11. [IF=3.757] Wu-Dan Cai et al."Hypoglycemic benefit and potential mechanism of a polysaccharide from Hericium erinaceus in streptozotoxin-induced diabetic rats."Process Biochem. 2020 Jan;88:180 12. [IF=3.718] K e et al."Glucose-lowering activity of dark tea protein extract by modulating spleen–brain axis of diabetic mice."Brit J Nutr. 2020 Dec;126(7):961-969 13. [IF=3.414] Yan Li et al."Dezhou donkey (Equus asinus) milk a potential treatment strategy for type 2 diabetes."J Ethnopharmacol. 2020 Jan;246:112221 14. [IF=5.34] Yi Kuang et al.A network pharmacology-based strategy to explore the pharmacological mechanisms of Antrodia camphorata and antcin K for treating type II diabetes mellitus.Phytomedicine. 2021 Nov;:153851 15. [IF=7.658] Guang-Jie Tai et al."NLRP3 inflammasome links vascular senescence to diabetic vascular lesions."Pharmacol Res. 2022 Apr;178:106143 |
metformin - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | metformin is the first-line treatment of type 2 diabetes and the whole drug, mainly through increasing muscle, the sensitivity of peripheral tissues such as fat to insulin increases the uptake and utilization of glucose, promotes anaerobic glycolysis of sugar, inhibits hepatic gluconeogenesis, and reduces hepatic glucose output, inhibition of glucose uptake by intestinal wall cells reduces fasting and postprandial hyperglycemia. In addition, metformin also has a weight loss effect, and can inhibit the biosynthesis and storage of cholesterol, reduce triglyceride and total cholesterol levels, improve vascular endothelial cell function, increase blood flow, it is especially suitable for obese or overweight patients with type 2 diabetes to prevent the occurrence and development of diabetic macrovascular complications and reduce the incidence of cardiovascular events. |
| Usage history | in, Watanabe injected the extract of French clove into rats, it was found to have a surprising effect of lowering blood glucose in rats. Metformin was first identified and documented in the scientific literature in 1922 and was first synthesized by Emil Werner and James Bell. In 429, Slotta and Tschesche found that metformin was the most important component of the hypoglycemic effect of biguanides. Since the big star of lowering blood sugar was insulin, metformin could only be used as a second-and third-line drug for more than ten years. In 1950, the French diabetologist Jean Sterne began to study the hypoglycemic activity of the goat bean base (clove extract) in the school. Later, in the Aron laboratory in Paris, Sterne was inspired by the Gracia study report and began to study metformin and biguanide analogs in depth. In 1957, Sterne published his research and named metformin Glucophage. Metformin was included in the UK national formulary in 1958 and marketed by the Aron subsidiary in England and France. Phenformin is marketed in the United States and northern European countries, and buformin is marketed in Germany. Ten years after 1960, phenformin became a star drug because of its potent hypoglycemic ability, but doctors also gradually found that the side effects of lactic acid poisoning caused by Biguanides and higher Mortality Rate. In the seventies of the 20th century, the withdrawal of phenformin and buformin from the market and metformin were also questioned. The father of metformin, Sterne, was not discouraged and explored the side effects of metformin. Metformin was approved by the FDA for type 2 diabetes in 1994 after concerns about its side effects were broken down by a clinical study. In the mid-20th century, metformin was listed in France. In 1994, the US FDA approved the listing of metformin, almost all diabetes guidelines at home and abroad recommend metformin as the first-line, whole-course and basic treatment of type 2 diabetes. In recent years, new hypoglycemic drugs have emerged, but the status of metformin has not been shaken. |
| metformin is a biguanide oral hypoglycemic agent. Can promote adipose tissue uptake of glucose, so that muscle tissue anaerobic glycolysis increased, increase the use of glucose, reduce insulin resistance, reduce glucose absorption through the digestive tract, so that blood sugar decreased. For adults with non-insulin-dependent diabetes mellitus and partially dependent diabetes mellitus. For the sulfonylureas invalid treatment of the majority of juvenile diabetes, lean diabetes, the application of this product can also reduce blood sugar. It can be used in combination with sulfonylureas or insulin to enhance its hypoglycemic effect. Obese patients with this product can also reduce weight. | |
| pharmacological action | hypoglycemic effect of metformin: the hypoglycemic effect of this product is accurate, and sulfonylurea hypoglycemic drugs than without hypoglycemia reaction, for obese and non-obese non-insulin-dependent diabetes mellitus (NIDDM) are effective, for simple diet treatment is invalid with this product alone, can reduce its basal blood glucose concentration of 20% (usually 2mmol/L or 36mg/dl). It can improve oral or intravenous glucose tolerance test, and its hypoglycemic effect has nothing to do with blood glucose concentration, age, course of disease, body weight and basal insulin level, often combined with sulfonylurea in single sulfonylurea control is not satisfied with the patient, combined than single sulfonylurea can reduce blood sugar more than 20%, combined with insulin can reduce the amount of insulin. Hypoglycemic mechanism: ① the hypoglycemic mechanism of this product is different from that of sulfonylureas. It does not stimulate insulin secretion, and its hypoglycemic effect is mainly to increase the anaerobic glycolysis of sugar in surrounding tissues and increase the utilization of sugar, the role of the main site in the small intestine, animal experiments confirmed that the goods can increase the small intestine anaerobic glycolysis, jejunum sugar utilization increased by 20%. (2) inhibition of hepatic gluconeogenesis and reduction of hepatic glucose output due to secondary hypoglycaemia caused by reduction of gluconeogenesis. ③ by increasing the binding of insulin and insulin receptor, increase the clearance effect of insulin on blood sugar, because insulin resistance is the characteristic of NIDDM, this product by increasing the number of insulin receptors to reduce the number of receptor binding points and increase the number of low affinity binding points to improve the sensitivity of NIDDM patients to insulin. Animal tests have proved that the product has a post-receptor effect, which increases the production of glycogen stimulated by insulin, increases the phosphorylation of insulin receptor and increases the activity of tyrosine kinase. |
| indications | The hypoglycemic mechanism and characteristics of metformin determine that it runs through the whole course of prevention and treatment of diabetes and contributes to the prevention and treatment of diabetic complications, specifically, it includes the following aspects: 1. Prevention of diabetes can be conditionally applied to secondary prevention and tertiary prevention of diabetes. For people at high risk of diabetes, we should first adjust the lifestyle, develop a good diet, exercise habits. If the effect is not obvious, the blood sugar is still gradually increased to reach the "pre-diabetes" state, in particular, patients whose metabolic syndrome is derived from diabetes and obese IGT or IFG is derived from diabetes can use metformin to delay and prevent the progression of diabetes. 2, the initial treatment of diabetes, metformin as the cornerstone of the hypoglycemic drug status, is the preferred drug for patients with diabetes. Once diabetes is diagnosed, metformin should be the first choice unless contraindicated or drug intolerance exists. 3, long-term treatment of diabetes in the relevant guidelines and consensus at home and abroad, metformin is positioned in the first choice of diabetes treatment and throughout the whole drug, that is, unless the single drug efficacy is poor, it is not recommended to change the drug, treatment should be continued in combination with other hypoglycemic agents. 4, prevention and treatment of complications: metformin has many hypoglycemic benefits, its function of reducing triacylglycerol and protecting vascular endothelium can play anti-atherosclerosis and reduce the incidence of coronary heart disease, it is beneficial to reduce the risk of cardiovascular events and hypertension. |
| usage and dosage | Po: start 0.25g, 3 times a day, with or after meals. About 1 week later, according to the condition of the disease, it can be added to 0.5g each time, 3 times a day. Daily dose should not exceed 1.5g, so as to avoid hypoglycemia. |
| adverse reaction | 1. Gastrointestinal reaction, Nausea, Vomit, metallic taste in mouth, Diarrhea. 2. Can make blood lactic acid increased, even appear lactic acidosis. 3. Congestive heart failure, liver, renal insufficiency in patients with this product should be particularly cautious. Use with caution in pregnant women. Diabetic ketoacidosis, acute infection when disabled. 4. Dose adjustment should prevent hypoglycemia, Coma or acidemia. 5. Combined with dicoumarin can cause bleeding tendency, this product can increase the pressor effect of vasopressin. 6. Abdominal Pain, acidemia and hypothermia may occur if alcohol-containing beverages are taken at the same time. |
Last Update：2024-04-09 02:00:10
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View History
metformin
sulfonaphthol
762-13-0
哈喹诺
乙酰乙酰甲胺
2-(Diphenylphosphino)phenol
313545-41-4
ETHYL 3,3,3-TRIFLUORO-2-HYDROXY-PROPIONATE
1-Methyl-3-Hydroxy-Tetrahydropyrrole
E-Base
sulfonaphthol
762-13-0
哈喹诺
乙酰乙酰甲胺
2-(Diphenylphosphino)phenol
313545-41-4
ETHYL 3,3,3-TRIFLUORO-2-HYDROXY-PROPIONATE
1-Methyl-3-Hydroxy-Tetrahydropyrrole
E-Base