MF8

Metformin


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Chemical Component Summary

NameMetformin
SynonymsN,N-Dimethylimidodicarbonimidic diamide
Identifiers3-carbamimidoyl-1,1-dimethyl-guanidine
FormulaC4 H11 N5
Molecular Weight129.164
TypeNON-POLYMER
Isomeric SMILES[H]/N=C(/N)\N/C(=N\[H])/N(C)C
InChIInChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
InChIKeyXZWYZXLIPXDOLR-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count20
Chiral Atom Count0
Bond Count19
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB00331 
NameMetformin
Groups approved
DescriptionMetformin is a biguanide antihyperglycemic agent and first-line pharmacotherapy used in the management of type II diabetes.[L12207,A176173] Metformin is considered an antihyperglycemic drug because it lowers blood glucose concentrations in type II diabetes without causing hypoglycemia. It is commonly described as an "insulin sensitizer", leading to a decrease in insulin resistance and a clinically significant reduction of plasma fasting insulin levels.[A176173] Another well-known benefit of this drug is modest weight loss, making it an effective choice for obese patients type II diabetes.[A36559] Metformin was first approved in Canada in 1972,[A36552] and received subsequent FDA approval in the US in 1995.[L12207]
Synonyms
  • 1,1-Dimethylbiguanide
  • Metformin hydrochloride
  • Dimethylbiguanid
  • Metformine
  • Metformin
Brand Names
  • Glumetza
  • Segluromet
  • Appformin-D
  • Pioglitazone and Metformin Hydrochloride
  • Nra-metformin
Indication**Metformin immediate-release formulations** Metformin is indicated as an adjunct to diet and exercise to improve glycemic control in adults and pediatric patients ≥10 years old with type 2 diabetes mellitus.[L40243] **Metformin extended-release tablet (XR)** The extended-release formulation of metformin is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Safety in children has not been determined to this date.[L12207] **Metformin combination products** Metformin is a component of a variety of combination products with other anti-diabetic agents. It is indicated, along with diet and exercise, to improve glycemic control in adult patients with type 2 diabetes mellitus in combination with DPP-4 inhibitors ([sitagliptin], [linagliptin], [alogliptin], or [saxagliptin]),[L11479,L40248,L40253,L40258,L40263] in combination with SGLT2 inhibitors ([canagliflozin], [empagliflozin], [ertugliflozin], or [dapagliflozin]),[L11479,L30503,L1134,L13679,L38729] or in combination with [pioglitazone].[L11419]
Categories
  • Alimentary Tract and Metabolism
  • Amidines
  • Biguanides
  • Blood Glucose Lowering Agents
  • Drugs that are Mainly Renally Excreted
ATC-Code
  • A10BD23
  • A10BD02
  • A10BD18
  • A10BD11
  • A10BD25
CAS number657-24-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Electron transfer flavoprotein-ubiquinone oxidoreductase, mitochondrialMLVPLAKLSCLAYQCFHALKIKKNYLPLCATRWSSTSTVPRITTHYTIYP...unknowninhibitor
5'-AMP-activated protein kinase subunit beta-1MGNTSSERAALERHGGHKTPRRDSSGGTKDGDRPKILMDSPEDADLFHSE...unknowninducer,activator
Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmicMASKKVCIVGSGNWGSAIAKIVGGNAAQLAQFDPRVTMWVFEEDIGGKKL...unknowninhibitor
Solute carrier family 22 member 1MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...unknownsubstrate
Solute carrier family 22 member 2MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1431
PubChem 6373215, 4091
ChEMBL CHEMBL1431
ChEBI CHEBI:6801
CCDC/CSD JAMRIY03, KONCAT, YOKWAY, JAMRIY, WOGSUI, JOQTEQ, ETIVUY, JAMRIY01, JOQTIU, JEHLAM, SAFQIB, GOLGIA, PAJCAF, PAJBUY, NOZGOB, OJOSUC02, YOKVUR, HULBUL, HUZLUJ, APOSAB, JAMRIY02, VAPQOU, PAJCAF01, UVIFUD, XAJXAL, JEDGIM, JAMRIY05, FETCEQ, ACUJUH, MAXJII
COD 7218481, 2233344, 2014445, 2014444