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657-24-9 molecular structure
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1-carbamimidamido-N,N-dimethylmethanimidamide

ChemBase ID: 215
Molecular Formular: C4H11N5
Molecular Mass: 129.16364
Monoisotopic Mass: 129.10144538
SMILES and InChIs

SMILES:
NC(=N)NC(=N)N(C)C
Canonical SMILES:
CN(C(=N)NC(=N)N)C
InChI:
InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
InChIKey:
XZWYZXLIPXDOLR-UHFFFAOYSA-N

Cite this record

CBID:215 http://www.chembase.cn/molecule-215.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-carbamimidamido-N,N-dimethylmethanimidamide
IUPAC Traditional name
metformin
Brand Name
Teva-Metformin
Sandoz Metformin
PMS-Metformin
Ran-Metformin
Mylan-Metformin
Apo-Metformin
Fortamet
Gen-Metformin
Glucophage
Glucophage XR
Glycon
Novo-Metformin
Nu-Metformin
Riomet
Glumetza
Ratio-Metformin
Synonyms
Metformin HCL
metformin hydrochloride
Metformin
CAS Number
657-24-9
PubChem SID
160963678
46507752
PubChem CID
4091

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00331 external link
PubChem 4091 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -5.7474184  LogD (pH = 7.4) -5.6176996 
Log P -0.91842926  Molar Refractivity 56.6427 cm3
Polarizability 12.998098 Å3 Polar Surface Area 88.99 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P -1.83  LOG S -1.97 
Solubility (Water) 1.38e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
Freely soluble as HCl salt expand Show data source
Hydrophobicity(logP)
-0.5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00331 external link
Item Information
Drug Groups approved
Description Metformin is a biguanide antihyperglycemic agent used for treating non-insulin-dependent diabetes mellitus (NIDDM). It improves glycemic control by decreasing hepatic glucose production, decreasing glucose absorption and increasing insulin-mediated glucose uptake. Metformin is the only oral antihyperglycemic agent that is not associated with weight gain. Metformin may induce weight loss and is the drug of choice for obese NIDDM patients. When used alone, metformin does not cause hypoglycemia; however, it may potentiate the hypoglycemic effects of sulfonylureas and insulin. Its main side effects are dyspepsia, nausea and diarrhea. Dose titration and/or use of smaller divided doses may decrease side effects. Metformin should be avoided in those with severely compromised renal function (creatinine clearance < 30 ml/min), acute/decompensated heart failure, severe liver disease and for 48 hours after the use of iodinated contrast dyes due to the risk of lactic acidosis. Lower doses should be used in the elderly and those with decreased renal function. Metformin decreases fasting plasma glucose, postprandial blood glucose and glycosolated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Metformin may also have a positive effect on lipid levels.
Indication 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).
Pharmacology Metformin is an oral antihyperglycemic agent that improves glucose tolerance in patients with NIDDM, lowering both basal and postprandial plasma glucose. Metformin is not chemically or pharmacologically related to any other class of oral antihyperglycemic agents. Unlike sulfonylureas, metformin does not produce hypoglycemia in either patients with NIDDM or healthy subjects and does not cause hyperinsulinemia. Metformin does not affect insulin secretion.
Toxicity 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.
Affected Organisms
Humans and other mammals
Biotransformation Metformin is not metabolized.
Absorption 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.
Half Life 6.2 hours. Duration of action is 8-12 hours.
Protein Binding Metformin is negligibly bound to plasma proteins.
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.
Distribution 654 L for metformin 850 mg administered as a single dose. The volume of distribution following IV administration is 63-276 L, likely due to less binding in the GI tract and/or different methods used to determine volume of distribution.
Clearance 718-1552 mL/minute following single oral dose of 0.5-1.5 g. Metformin is removed by hemodialysis at a rate of approximately 170 ml/min under good hemodynamic conditions.
References
Witters LA: The blooming of the French lilac. J Clin Invest. 2001 Oct;108(8):1105-7. [Pubmed]
UNGAR G, FREEDMAN L, SHAPIRO SL: Pharmacological studies of a new oral hypoglycemic drug. Proc Soc Exp Biol Med. 1957 May;95(1):190-2. [Pubmed]
Lord JM, Flight IH, Norman RJ: Metformin in polycystic ovary syndrome: systematic review and meta-analysis. BMJ. 2003 Oct 25;327(7421):951-3. [Pubmed]
Marchesini G, Brizi M, Bianchi G, Tomassetti S, Zoli M, Melchionda N: Metformin in non-alcoholic steatohepatitis. Lancet. 2001 Sep 15;358(9285):893-4. [Pubmed]
Nair S, Diehl AM, Wiseman M, Farr GH Jr, Perrillo RP: Metformin in the treatment of non-alcoholic steatohepatitis: a pilot open label trial. Aliment Pharmacol Ther. 2004 Jul 1;20(1):23-8. [Pubmed]
External Links
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REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Witters LA: The blooming of the French lilac. J Clin Invest. 2001 Oct;108(8):1105-7. Pubmed
  • • UNGAR G, FREEDMAN L, SHAPIRO SL: Pharmacological studies of a new oral hypoglycemic drug. Proc Soc Exp Biol Med. 1957 May;95(1):190-2. Pubmed
  • • Lord JM, Flight IH, Norman RJ: Metformin in polycystic ovary syndrome: systematic review and meta-analysis. BMJ. 2003 Oct 25;327(7421):951-3. Pubmed
  • • Marchesini G, Brizi M, Bianchi G, Tomassetti S, Zoli M, Melchionda N: Metformin in non-alcoholic steatohepatitis. Lancet. 2001 Sep 15;358(9285):893-4. Pubmed
  • • Nair S, Diehl AM, Wiseman M, Farr GH Jr, Perrillo RP: Metformin in the treatment of non-alcoholic steatohepatitis: a pilot open label trial. Aliment Pharmacol Ther. 2004 Jul 1;20(1):23-8. Pubmed
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PATENTS

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