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Record Information
Version4.0
Creation Date2006-05-18 08:29:34 UTC
Update Date2017-09-27 08:24:09 UTC
HMDB IDHMDB0001921
Secondary Accession Numbers
  • HMDB01921
Metabolite Identification
Common Name1,1-Dimethylbiguanide
Description1,1-Dimethylbiguanide or Metformin is a biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. Metformin is the most popular anti-diabetic drug in the United States and one of the most prescribed drugs in the country overall, with nearly 35 million prescriptions filled in 2006 for generic metformin alone.
Structure
Thumb
Synonyms
ValueSource
1,1-Dimethyl biguanideHMDB
DiabefagosHMDB
DiabexHMDB
DiaforminHMDB
DianbenHMDB
DimethylbiguanideHMDB
DMBGHMDB
FortametHMDB
GlucophageHMDB
GlumetzaHMDB
MeguanHMDB
MetforminHMDB
MetiguanideHMDB
N,N-DimethylbiguanideHMDB
N1,N1-DimethylbiguanideHMDB
ObimetHMDB
RiometHMDB
DimethylbiguanidineMeSH
DimethylguanylguanidineMeSH
Metformin HCLMeSH
HCL, MetforminMeSH
Hydrochloride, metforminMeSH
Metformin hydrochlorideMeSH
Chemical FormulaC4H11N5
Average Molecular Weight129.1636
Monoisotopic Molecular Weight129.101445377
IUPAC Name1-carbamimidamido-N,N-dimethylmethanimidamide
Traditional Namemetformin
CAS Registry Number1115-70-4
SMILES
CN(C)C(=N)NC(N)=N
InChI Identifier
InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
InChI KeyXZWYZXLIPXDOLR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biguanides. These are organic compounds containing two N-linked guanidines.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentBiguanides
Alternative Parents
Substituents
  • Biguanide
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    Nervous system disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point223 - 226 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.38 g/LALOGPS
logP-1.8ALOGPS
logP-0.92ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)12.33ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area88.99 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.64 m³·mol⁻¹ChemAxon
Polarizability13.43 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-9046e2aa0408a0396007View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01qi-9700000000-a6b98d87cc840a082179View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00dr-9000000000-8e80f301bad045540477View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-bd8aed328c944acd1270View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-03l9-9300000000-3d585674ffe84238e5bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00di-9000000000-ee68820579ebe4d31082View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9000000000-4312e7e5e1b0dd9ef936View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-9000000000-053d63fe09a95fc1d544View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0229-9100000000-7fe999a9d1aaae3bbe53View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-c235cd5d0dda3f3c28d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-0fa445716bfc24131a75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-3900000000-dee37da326e6f0b2c56aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-45bd1f8c6d2dc4f38944View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1900000000-38f3dedb5c19900cdefbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-7900000000-bf5d1092aa372c303d61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03l9-9300000000-06a99f0dff4b41a23cfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-022i-9100000000-811c9e7cf8b30b27c0f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-9000000000-d34b9b3ab9eb78317ebaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-4d53ac0f7dfaf860e784View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-6900000000-03a99ea4f96636a6d5e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9000000000-24ee057ec9505ccf8d3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-9000000000-bc7faff99aaa83f5e600View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9300000000-e145cf58ec0f6be503abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9100000000-0cc6d6ceac8192964ee4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f47eab8fa0fd4177cfddView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
Tissue Location
  • Erythrocyte
  • Liver
  • Muscle
  • Skeletal Muscle
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.0 (0.0060-12.07) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022739
KNApSAcK IDNot Available
Chemspider ID3949
KEGG Compound IDC07151
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlucophage
METLIN ID6390
PubChem Compound4091
PDB IDNot Available
ChEBI ID6801
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Musi N, Hirshman MF, Nygren J, Svanfeldt M, Bavenholm P, Rooyackers O, Zhou G, Williamson JM, Ljunqvist O, Efendic S, Moller DE, Thorell A, Goodyear LJ: Metformin increases AMP-activated protein kinase activity in skeletal muscle of subjects with type 2 diabetes. Diabetes. 2002 Jul;51(7):2074-81. [PubMed:12086935 ]
  2. Bridger T, MacDonald S, Baltzer F, Rodd C: Randomized placebo-controlled trial of metformin for adolescents with polycystic ovary syndrome. Arch Pediatr Adolesc Med. 2006 Mar;160(3):241-6. [PubMed:16520442 ]
  3. Seale FG 4th, Robinson RD, Neal GS: Association of metformin and pregnancy in the polycystic ovary syndrome. A report of three cases. J Reprod Med. 2000 Jun;45(6):507-10. [PubMed:10900588 ]
  4. Briggs GG, Ambrose PJ, Nageotte MP, Padilla G, Wan S: Excretion of metformin into breast milk and the effect on nursing infants. Obstet Gynecol. 2005 Jun;105(6):1437-41. [PubMed:15932841 ]
  5. De Jager J, Kooy A, Lehert P, Bets D, Wulffele MG, Teerlink T, Scheffer PG, Schalkwijk CG, Donker AJ, Stehouwer CD: Effects of short-term treatment with metformin on markers of endothelial function and inflammatory activity in type 2 diabetes mellitus: a randomized, placebo-controlled trial. J Intern Med. 2005 Jan;257(1):100-9. [PubMed:15606381 ]
  6. Mughal MA, Jan M, Maheri WM, Memon MY, Ali M: The effect of metformin on glycemic control, serum lipids and lipoproteins in diet alone and sulfonylurea-treated type 2 diabetic patients with sub-optimal metabolic control. J Pak Med Assoc. 2000 Nov;50(11):381-6. [PubMed:11126815 ]
  7. Einhorn D, Rendell M, Rosenzweig J, Egan JW, Mathisen AL, Schneider RL: Pioglitazone hydrochloride in combination with metformin in the treatment of type 2 diabetes mellitus: a randomized, placebo-controlled study. The Pioglitazone 027 Study Group. Clin Ther. 2000 Dec;22(12):1395-409. [PubMed:11192132 ]
  8. Robert F, Fendri S, Hary L, Lacroix C, Andrejak M, Lalau JD: Kinetics of plasma and erythrocyte metformin after acute administration in healthy subjects. Diabetes Metab. 2003 Jun;29(3):279-83. [PubMed:12909816 ]
  9. Radziuk J, Pye S: Hepatic glucose uptake, gluconeogenesis and the regulation of glycogen synthesis. Diabetes Metab Res Rev. 2001 Jul-Aug;17(4):250-72. [PubMed:11544610 ]
  10. Morin-Papunen LC, Vauhkonen I, Koivunen RM, Ruokonen A, Martikainen HK, Tapanainen JS: Endocrine and metabolic effects of metformin versus ethinyl estradiol-cyproterone acetate in obese women with polycystic ovary syndrome: a randomized study. J Clin Endocrinol Metab. 2000 Sep;85(9):3161-8. [PubMed:10999803 ]
  11. Marathe PH, Wen Y, Norton J, Greene DS, Barbhaiya RH, Wilding IR: Effect of altered gastric emptying and gastrointestinal motility on metformin absorption. Br J Clin Pharmacol. 2000 Oct;50(4):325-32. [PubMed:11012555 ]
  12. Gore DC, Wolf SE, Sanford A, Herndon DN, Wolfe RR: Influence of metformin on glucose intolerance and muscle catabolism following severe burn injury. Ann Surg. 2005 Feb;241(2):334-42. [PubMed:15650645 ]
  13. Gillies PS, Dunn CJ: Pioglitazone. Drugs. 2000 Aug;60(2):333-43; discussion 344-5. [PubMed:10983737 ]
  14. Hale TW, Kristensen JH, Hackett LP, Kohan R, Ilett KF: Transfer of metformin into human milk. Diabetologia. 2002 Nov;45(11):1509-14. Epub 2002 Sep 25. [PubMed:12436333 ]
  15. Lalau JD, Lacroix C: Measurement of metformin concentration in erythrocytes: clinical implications. Diabetes Obes Metab. 2003 Mar;5(2):93-8. [PubMed:12630933 ]
  16. Kouki T, Takasu N, Nakachi A, Tamanaha T, Komiya I, Tawata M: Low-dose metformin improves hyperglycaemia related to myotonic dystrophy. Diabet Med. 2005 Mar;22(3):346-7. [PubMed:15717887 ]
  17. Magalhaes FO, Gouveia LM, Torquato MT, Paccola GM, Piccinato CE, Foss MC: Metformin increases blood flow and forearm glucose uptake in a group of non-obese type 2 diabetes patients. Horm Metab Res. 2006 Aug;38(8):513-7. [PubMed:16941277 ]
  18. Gore DC, Herndon DN, Wolfe RR: Comparison of peripheral metabolic effects of insulin and metformin following severe burn injury. J Trauma. 2005 Aug;59(2):316-22; discussion 322-3. [PubMed:16294070 ]
  19. Amador-Licona N, Guizar-Mendoza J, Vargas E, Sanchez-Camargo G, Zamora-Mata L: The short-term effect of a switch from glibenclamide to metformin on blood pressure and microalbuminuria in patients with type 2 diabetes mellitus. Arch Med Res. 2000 Nov-Dec;31(6):571-5. [PubMed:11257323 ]
  20. Carter D, Howlett HC, Wiernsperger NF, Bailey C: Effects of metformin on bile salt transport by monolayers of human intestinal Caco-2 cells. Diabetes Obes Metab. 2002 Nov;4(6):424-7. [PubMed:12406042 ]