1.0 2009-07-30 17:59:02 UTC 2026-05-14 16:35:41 UTC T3D3522 1,1-Dimethylbiguanide SmallMolecule 1,1-Dimethylbiguanide belongs to the guanidines, a subclass of organonitrogen compounds within the organic compounds. This exogenous solid has the formula C4H11N5 and an average molecular weight of 129.16 g/mol. It is identified as a drug (PMC4329414, PMC6130437), agonist (PMC7136780), antimalarial (PMC7012204), and hypoglycemic agent. The compound is recorded in sources including blood glucose lowering drugs, food preservation, and various household and electronic products, with oral exposure being the recorded route. It has been detected in the liver, muscle, skeletal muscle, and erythrocytes. As an antihyperglycemic agent, it decreases hepatic glucose production, decreases intestinal absorption of glucose, and improves insulin sensitivity by increasing peripheral glucose uptake and utilization. Its protein targets include 5'-AMP-activated protein kinase subunit beta-1 (PRKAB1) and the proteins DPP4, ETFDH, SLC22A1, and SLC22A2, among others. 1,1-Dimethylbiguanide is used as a treatment for diabetes mellitus (PMC13163680), type 2 diabetes mellitus (PMC3539408), gestational diabetes (PMC3959776), obesity (PMC11505606), polycystic ovary syndrome (PMC10819319, PMC3959776, PMC4329414), cancer (PMC10819319, PMC6678564, PMC9563310), melanoma (PMC6385607), abortion (PMC13409969), and symptoms including abdominal pain, diarrhea, and bloody stool (PMC9453768). Therapeutic effects have been noted for depression (PMC6721393, PMC7765295), anxiety (PMC6721393), pain (PMC12684957), hepatic steatosis (PMC4210865), and various cancers, including liver cancer (PMC10674350, PMC5584165), hepatocellular carcinoma (PMC5584165), prostate cancer (PMC5847527), ovarian cancer (PMC6678564), and melanoma (PMC5584165). Associated health effects include fever, anemia, and diarrhea (PMC13040807), as well as diarrhea (PMC12016791) and an increase in lactic acidosis (PMC12453945). Drug Food Toxin Synthetic Toxin Organic Compound Amine Amide Drug Food Toxin Hypoglycemic Agent Metabolite Synthetic Compound Antidiabetic Agent 1,1-Dimethyl biguanide 1-carbamimidamido-N,N-dimethylmethanimidamide Apo-Metformin Diabefagos Diabex Diaformin Dianben Dimethylbiguanid Dimethylbiguanide DMBG Fortamet Gen-Metformin Glucophage Glucophage XR Glumetza Haurymellin Meguan Metformin METFORMIN Metformina Metformine Metformine pamoate Metforminum Metiguanide Mylan-Metformin N,N-Dimethylbiguanide N,N-Dimethylimidodicarbonimidic diamide N1,N1-Dimethylbiguanide Novo-Metformin Nu-Metformin Obimet PMS-Metformin Ran-Metformin Ratio-Metformin Riomet Sandoz Metformin Teva-Metformin C4H11N5 129.1636 129.101445377 1-carbamimidamido-N,N-dimethylmethanimidamide metformin 657-24-9 CN(C)C(=N)NC(N)=N InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8) XZWYZXLIPXDOLR-UHFFFAOYSA-N Organic compounds Organic nitrogen compounds Organonitrogen compounds Guanidines Biguanides Carboximidamides Hydrocarbon derivatives Imines Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound Biguanide Carboximidamide Hydrocarbon derivative Imine Organic 1,3-dipolar compound Organopnictogen compound Propargyl-type 1,3-dipolar organic compound Aliphatic acyclic compounds guanidines Detected and Not Quantified Exogenous Cytoplasm Extracellular Erythrocyte Liver Muscle Skeletal Muscle 1,1-Dimethylbiguanide Drug Metabolism Pathway SMP0145440 Solid White powder. melting_point 223-226°C solubility Freely soluble as HCl salt logp -0.5 logp -1.83 ALOGPS logs -1.97 ALOGPS solubility 1.38e+00 g/l ALOGPS logp -0.92 ChemAxon pka_strongest_basic 12.33 ChemAxon iupac 1-carbamimidamido-N,N-dimethylmethanimidamide ChemAxon average_mass 129.1636 ChemAxon mono_mass 129.101445377 ChemAxon smiles CN(C)C(=N)NC(N)=N ChemAxon formula C4H11N5 ChemAxon inchi InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8) ChemAxon inchikey XZWYZXLIPXDOLR-UHFFFAOYSA-N ChemAxon polar_surface_area 88.99 ChemAxon refractivity 56.64 ChemAxon polarizability 13.43 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 2 ChemAxon formal_charge 0 ChemAxon Absorbed over 6 hours, bioavailability is 50 to 60% under fasting conditions. Administration with food decreases and delays absorption. Some evidence indicates that the level of absorption is not dose-related, suggesting that absorption occurs through a saturable process. Limited data from animal and human cell cultures indicate that absorption occurs through a passive, non-saturable process, possibly involving a paracellular route. Peak action occurs 3 hours after oral administration. Metformin's mechanisms of action differ from other classes of oral antihyperglycemic agents. Metformin decreases blood glucose levels by decreasing hepatic glucose production, decreasing intestinal absorption of glucose, and improving insulin sensitivity by increasing peripheral glucose uptake and utilization. These effects are mediated by the initial activation by metformin of AMP-activated protein kinase (AMPK), a liver enzyme that plays an important role in insulin signaling, whole body energy balance, and the metabolism of glucose and fats. Activation of AMPK is required for metformin's inhibitory effect on the production of glucose by liver cells. Increased peripheral utilization of glucose may be due to improved insulin binding to insulin receptors. Metformin administration also increases AMPK activity in skeletal muscle. AMPK is known to cause GLUT4 deployment to the plasma membrane, resulting in insulin-independent glucose uptake. The rare side effect, lactic acidosis, is thought to be caused by decreased liver uptake of serum lactate, one of the substrates of gluconeogenesis. In those with healthy renal function, the slight excess is simply cleared. However, those with severe renal impairment may accumulate clinically significant serum lactic acid levels. Other conditions that may precipitate lactic acidosis include severe hepatic disease and acute/decompensated heart failure. Acute oral toxicity (LD₅₀): 350 mg/kg [Rabbit]. Metformin is not metabolized. Route of Elimination: Intravenous single-dose studies in normal subjects demonstrate that metformin is excreted unchanged in the urine and does not undergo hepatic metabolism (no metabolites have been identified in humans) nor biliary excretion. Approximately 90% of the drug is eliminated in 24 hours in those with healthy renal function. Renal clearance of metformin is approximately 3.5 times that of creatinine clearance, indicating the tubular secretion is the primary mode of metformin elimination. Half Life: 6.2 hours. Duration of action is 8-12 hours. Acute oral toxicity (LD₅₀): 350 mg/kg [Rabbit]. No indication of carcinogenicity to humans (not listed by IARC). For use as an adjunct to diet and exercise in adult patients (18 years and older) with NIDDM. May also be used for the management of metabolic and reproductive abnormalities associated with polycystic ovary syndrome (PCOS). Jentadueto is for the treatment of patients when both linagliptin and metformin is appropriate. #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f3bb3f24608> Acute oral toxicity (LD₅₀): 350 mg/kg [Rabbit]. It would be expected that adverse reactions of a more intense character including epigastric discomfort, nausea, and vomiting followed by diarrhea, drowsiness, weakness, dizziness, malaise and headache might be seen. DB00331 HMDB01921 4091 CHEMBL1431 3949 C07151 125853 184700 6801 Metformin Metformin 11602616 13432032 14576245 11567710 15225167 10900588 15932841 15606381 11126815 11192132 12909816 11544610 10999803 12086935 11012555 15650645 10983737 12436333 12630933 15717887 16941277 16294070 16520442 11257323 12406042 BE0000254 Metformin's pharmacologic mechanisms of action are different from other classes of oral antihyperglycemic agents. Metformin decreases hepatic glucose production, decreases intestinal absorption of glucose, and improves insulin sensitivity by increasing peripheral glucose uptake and utilization. BE0000854 IC50 29 uM BindingDB 50229665 BE0003648 IC50 2010 uM BindingDB 50229665 BE0003647 IC50 1700 uM BindingDB 50229665 BE0003887 BE0000208 BE0000702 BE0003657