Metformin

Base Information

• Chemical Name: Metformin
• CAS No.: 657-24-9
• Molecular Formula: C4H11N5
• Molecular Weight: 129.165
• European Community (EC) Number: 211-517-8
• UNII: 9100L32L2N
• DSSTox Substance ID: DTXSID2023270
• Nikkaji Number: J9.463C
• Wikipedia: Metformin
• Wikidata: Q19484
• NCI Thesaurus Code: C61612
• RXCUI: 6809
• Pharos Ligand ID: JGRU8YTL5RPV
• Metabolomics Workbench ID: 73614
• ChEMBL ID: CHEMBL1431
• Mol file: 657-24-9.mol

Synonyms:Dimethylbiguanidine;Dimethylguanylguanidine;Glucophage;HCl, Metformin;Hydrochloride, Metformin;Metformin;Metformin HCl;Metformin Hydrochloride

Chemical Property of Metformin

Chemical Property:

• Melting Point: 199-200 °C
• Refractive Index: 1.5760 (estimate)
• Boiling Point: 224.1 °C at 760 mmHg
• PKA: pKa 2.8(H2O,t =32) (Uncertain)
• Flash Point: 89.3 °C
• PSA: 88.99000
• Density: 1.28 g/cm³
• LogP: 0.25650
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Acetonitrile (Slightly), Aqueous Acid (Slightly), Dichloromethane (Slightly), DM
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 129.10144537
• Heavy Atom Count: 9
• Complexity: 132

Purity/Quality:

99%, ^*data from raw suppliers

Metformin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antidiabetic Agents
• Canonical SMILES: CN(C)C(=N)N=C(N)N
• Recent ClinicalTrials: iGlarLixi vs IDegAsp in Chinese Participants After OAD(s)
• Recent EU Clinical Trials: Efficacy of metformin versus sitagliptin on benign thyroid nodules size in type 2 diabetes: a 2-years prospective multicentric study
• Recent NIPH Clinical Trials: Clinical pharmacology study to evaluate the drug-drug interactions of TAS-115 in healthy subjects
• Description: The study of metformin and its hypoglycemic effects originated from the study of goat’s rue plants, also known as Galega officinalis(French lilac). Goat’s rues are native plants in the Middle East and introduced to Europe later and have been used as forage and ornamental plants throughout the world, including China. As early as in the Middle Ages in Europe, it was found that goat’s rues could ease polyuria, which is one of the typical symptoms of diabetes. While goat’s rues were used to treat a variety of other diseases in the Middle Ages, it was found to cause poisoning symptoms in livestock. Goat’s rues are still used as medical plants at present, mainly for diabetes, diuretic, hepatoprotection, aiding in digestion and promoting lactation, etc. In China, goat’s rues were recorded first in the dictionary of Chinese seed plants and mainly used for the treatment of diabetes. However, because of high toxicity, it is rarely used in traditional Chinese medicines at present.
• Physical properties: Appearance: white crystalline or crystalline powder, odorless. Solubility: freely soluble in water, soluble in methanol, slightly soluble in ethanol, and insoluble in chloroform or ether. Melting point: 223–226°C.
• Uses: non-insulin dependent diabetes mellitus
• Indications: Metformin (Glucophage) was used in Europe for many years before it was approved for use in the United States in 1995. Metformin is the only approved biguanide for the treatment of patients with NIDDM that are refractory to dietary management alone. Metformin does not affect insulin secretion but requires the presence of insulin to be effective. The exact mechanism of metformin’s action is not clear, but it does decrease hepatic glucose production and increase peripheral glucose uptake. When used as monotherapy, metformin rarely causes hypoglycemia.
• Therapeutic Function: Oral hypoglycemic
• Biological Functions: Metformin can lower free fatty acid concentrations by 10 to 30%. This antilipolytic effect may help to explain the reduction in gluconeogenesis through reduced levels of available substrate (65). When given as a monotherapy, metformin treatment does not lead to hypoglycemia, so it is better described as an antihyperglycemic agent rather than a hypoglycemic agent.
• Clinical Use: Metformin works best in patients with significant hyperglycemia and is often considered first-line therapy in the treatment of mild to moderate type II overweight diabetics who demonstrate insulin resistance. The United Kingdom Prospective Diabetes Study demonstrated a marked reduction in cardiovascular comorbidities and diabetic complications in metformintreated individuals. Metformin has also been used to treat hirsutism in individuals with polycystic ovarian syndrome and may enhance fertility in these women, perhaps by decreasing androgen levels and enhancing insulin sensitivity.

Technology Process of Metformin

There total 11 articles about Metformin 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: 100.0%

metformin hydrochloride (1115-70-4) → dimethylbiguanide (657-24-9)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 0.5h;

Reference yield: 99.0%

metformin hydrochloride (1115-70-4) → metformin (657-24-9)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 0.5h;

DOI:10.1016/j.bioorg.2019.103444

Reference yield: 99.0%

N,N-dimethyl imidodicarbonimidic diamide hydrochloride (1115-70-4) → metformin (657-24-9)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 0.5h;

DOI:10.1021/jm900274q

upstream raw materials:

N,N-dimethylammonium chloride

N-Cyanoguanidine

dimethyl amine

metformin hydrochloride

Downstream raw materials:

N²,N²-dimethyl-1,3,5-triazine-2,4-diamine

N,N-dimethyl-N'-sulfanilyl-guanidine

N-(4-methylphenylsulfonyl)metformin

1-(4-Oxo-5,5-diphenyl-2-imidazolin-2-yl)-3,3-dimethylguanidin

Refernces

• 1、 Huttunen, Kristiina M.,Markowicz-Piasecka, Magdalena,Sikora, Joanna,Zajda, Agnieszka. "Novel halogenated sulfonamide biguanides with anti-coagulation properties". . . Retrieved 2019.
• 2、 Feng, Wen-Quan,Wang, Ling-Yang,Gao, Jie,Zhao, Ming-Yu,Li, Yan-Tuan,Wu, Zhi-Yong,Yan, Cui-Wei. "Solid state and solubility study of a potential anticancer drug-drug molecular salt of diclofenac and metformin". . . Retrieved 2021.
• 3、 Markowicz-Piasecka, Magdalena,Sadkowska, Adrianna,Sikora, Joanna,Broncel, Marlena,Huttunen, Kristiina M.. "Novel sulfonamide-based analogs of metformin exert promising anti-coagulant effects without compromising glucose-lowering activity". . p. 1 - 28. Retrieved 2020.
• 4、 -. "5-substituted 2,4-thiazolidinediones (thiohydantoins), pseudothiohydantoins, and propseudothiohydantoins for use as antiviral agents". Page/Page column 13-14. . Retrieved 2020/06/03.