Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H11N5 |
Molecular Weight | 129.1636 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C(=N)NC(N)=N
InChI
InChIKey=XZWYZXLIPXDOLR-UHFFFAOYSA-N
InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
Molecular Formula | C4H11N5 |
Molecular Weight | 129.1636 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://packageinserts.bms.com/pi/pi_glucophage.pdfCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25333032 | http://www.rsc.org/images/eic_nov2011_metformin_tcm18-210010.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22117616
Sources: https://packageinserts.bms.com/pi/pi_glucophage.pdf
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25333032 | http://www.rsc.org/images/eic_nov2011_metformin_tcm18-210010.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22117616
Metformin is the most widely used drug to treat type 2 diabetes, and is one of only two oral antidiabetic drugs on the World Health Organization (WHO) list of essential medicines.
Metformin is an antihyperglycemic agent which improves glucose tolerance in patients with type 2 diabetes, lowering both basal and postprandial plasma glucose. Metformin decreases hepatic glucose production, decreases intestinal absorption of glucose, and improves insulin sensitivity by increasing peripheral glucose uptake and utilization. However, we still do not completely understand its mechanisms of action. The main effect of this drug from the biguanide family is to acutely decrease hepatic glucose production, mostly through a mild and transient inhibition of the mitochondrial respiratory chain complex I. In addition, the resulting decrease in hepatic energy status activates AMPK (AMP-activated protein kinase), a cellular metabolic sensor, providing a generally accepted mechanism for the action of metformin on hepatic gluconeogenesis. The use of metformin, the most commonly prescribed drug for type 2 diabetes, was repeatedly associated with the decreased risk of the occurrence of various types of cancers, especially of pancreas and colon and hepatocellular carcinoma.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0006094 |
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Target ID: CHEMBL2363065 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22117616 |
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Target ID: CHEMBL2096907 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22117616 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | GLUCOPHAGE Approved UseMetformin hydrochloride tablets, USP is indicated as an adjunct to diet and exercise to improve glycemic control in adults and children with type 2 diabetes mellitus. Metformin hydrochloride extended-release tablets, USP is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Launch Date1995 |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
815.39 ng/mL |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: |
METFORMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7694.78 ng × h/mL |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: |
METFORMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.19 h |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: |
METFORMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | yes (co-administration study) Comment: Co-administration of cimetidine, pyrimethamine, trimethoprim, lansoprazole, dolutegravir and vandetanib with metformin has been shown to increase its AUC by 1.2 to 1.7-fold Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
Pioglitazone. | 2000 Aug |
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Association of metformin and pregnancy in the polycystic ovary syndrome. A report of three cases. | 2000 Jun |
|
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. | 2000 Nov |
|
The short-term effect of a switch from glibenclamide to metformin on blood pressure and microalbuminuria in patients with type 2 diabetes mellitus. | 2000 Nov-Dec |
|
[Marked creatine-phosphokinase elevation in myopathy after treatment with bezafibrate]. | 2000 Sep |
|
Endocrine and metabolic effects of metformin versus ethinyl estradiol-cyproterone acetate in obese women with polycystic ovary syndrome: a randomized study. | 2000 Sep |
|
Increased intake of calcium reverses vitamin B12 malabsorption induced by metformin. | 2000 Sep |
|
[Prevention of lactic acidosis due to metformin intoxication in contrast media nephropathy]. | 2000 Sep 30 |
|
Metformin, the rebirth of a biguanide: mechanism of action and place in the prevention and treatment of insulin resistance. | 2001 |
|
Nuclear magnetic resonance studies of hepatic glucose metabolism in humans. | 2001 |
|
[Insulin sensitivity and polycystic ovarian syndrome]. | 2001 Apr |
|
Homocysteine and cardiovascular risk in patients with diabetes mellitus. | 2001 Apr |
|
Acute postoperative metabolic complications of diabetes. | 2001 Apr |
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Clinical review of glimepiride. | 2001 Apr |
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The effects of metformin on body mass index and glucose tolerance in obese adolescents with fasting hyperinsulinemia and a family history of type 2 diabetes. | 2001 Apr |
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Additive glucose-lowering effects of glucagon-like peptide-1 and metformin in type 2 diabetes. | 2001 Apr |
|
Improved endothelial function with metformin in type 2 diabetes mellitus. | 2001 Apr |
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ION-pair liquid chromatography technique for the estimation of metformin in its multicomponent dosage forms. | 2001 Apr |
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Metformin-associated lactic acidosis. | 2001 Apr |
|
[Metformin and intravascular contrast media. National guidelines 2001-03-16]. | 2001 Apr 18 |
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Mechanism of fat-induced hepatic gluconeogenesis: effect of metformin. | 2001 Aug |
|
Effect of metformin on fatty acid and glucose metabolism in freshly isolated hepatocytes and on specific gene expression in cultured hepatocytes. | 2001 Aug 15 |
|
Management of diabetes mellitus in three settings in Jamaica. | 2001 Feb |
|
Myositis, microvesicular hepatitis, and progression to cirrhosis from troglitazone added to simvastatin. | 2001 Feb |
|
Lactic acidosis update for critical care clinicians. | 2001 Feb |
|
Metformin increases the ovulatory rate and pregnancy rate from clomiphene citrate in patients with polycystic ovary syndrome who are resistant to clomiphene citrate alone. | 2001 Feb |
|
Combination therapy in type 2 diabetes: the role of repaglinide. | 2001 Jan 25 |
|
Metformin reduces weight, centripetal obesity, insulin, leptin, and low-density lipoprotein cholesterol in nondiabetic, morbidly obese subjects with body mass index greater than 30. | 2001 Jul |
|
Re: Contrast media-induced nephrotoxicity: identification of patients at risk and algorithms for prevention. | 2001 Jul |
|
Nateglinide. | 2001 Jul 1 |
|
Digestive hemorrhage caused by a Meckel's diverticulum in a metformin-treated patient: is there any connection? | 2001 Jun |
|
Pharmacokinetics of metformin gastric-retentive tablets in healthy volunteers. | 2001 Jun |
|
Use of urea containing dialysate to avoid disequilibrium syndrome, enabling intensive dialysis treatment of a diabetic patient with renal failure and severe metformin induced lactic acidosis. | 2001 Jun |
|
The effects of long-term metformin treatment on adrenal and ovarian steroidogenesis in women with polycystic ovary syndrome. | 2001 Jun |
|
The synergistic effect of miglitol plus metformin combination therapy in the treatment of type 2 diabetes. | 2001 Jun |
|
Comparison of the metabolic effects of metformin and troglitazone on fructose-induced insulin resistance in male Sprague-Dawley rats. | 2001 Mar |
|
Rosiglitazone. | 2001 Mar |
|
Insulin-lowering drugs in polycystic ovary syndrome. | 2001 Mar |
|
Improvement of glycemic control by 1 year of insulin therapy leads to a sustained decrease in sE-selectin concentrations in type 2 diabetes. | 2001 Mar |
|
[Role and modalities of insulin treatment in type 2 diabetics]. | 2001 Mar |
|
Metformin and the polycystic ovary syndrome. | 2001 Mar |
|
[Current and future aspects of oral antidiabetic agents in type 2 diabetes]. | 2001 May |
|
The oral insulin sensitizer, thiazolidinedione, increases plasma vascular endothelial growth factor in type 2 diabetic patients. | 2001 May |
|
Use of the ligand immunofunctional assay for human insulin-like growth factor ((IGF) binding protein-3 (IGFBP-3) to analyze IGFBP-3 proteolysis and igf-i bioavailability in healthy adults, GH-deficient and acromegalic patients, and diabetics. | 2001 May |
|
Cardiomyocyte dysfunction in sucrose-fed rats is associated with insulin resistance. | 2001 May |
|
The effect of a thiazolidinedione drug, troglitazone, on glycemia in patients with type 2 diabetes mellitus poorly controlled with sulfonylurea and metformin. A multicenter, randomized, double-blind, placebo-controlled trial. | 2001 May 1 |
|
[Metformin and anesthesia--how great is the risk of lactic acidosis]. | 2001 May 18 |
|
Thiazolidinediones but not metformin directly inhibit the steroidogenic enzymes P450c17 and 3beta -hydroxysteroid dehydrogenase. | 2001 May 18 |
|
Effect of a series of novel sulphonylthioureas on glucose tolerance in the obese fa/fa Zucker rat. | 2001 May-Jun |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://packageinserts.bms.com/pi/pi_glucophage.pdf
Recommended Dosing Schedule
Adults
The usual starting dose of GLUCOPHAGE Tablets is 500 mg twice a day or 850 mg once a day,
given with meals. In general, clinically significant responses are not seen at doses below 1500
mg per day. Dosage increases should be made in increments of 500 mg weekly or 850 mg every
2 weeks, up to a total of 2000 mg per day, given in divided doses. The dosage of
GLUCOPHAGE must be individualized on the basis of both effectiveness and tolerability.
Patients can also be titrated from 500 mg twice a day to 850 mg twice a day after 2 weeks. For
those patients requiring additional glycemic control, GLUCOPHAGE may be given to a
maximum daily dose of 2550 mg per day. Doses above 2000 mg may be better tolerated given
3 times a day with meals.
The usual starting dose of GLUCOPHAGE XR (metformin hydrochloride) Extended-Release
Tablets is 500 mg once daily with the evening meal. In general, clinically significant responses
are not seen at doses below 1500 mg per day. Dosage increases should be made in increments of
500 mg weekly, up to a maximum of 2000 mg once daily with the evening meal. The dosage of
GLUCOPHAGE XR must be individualized on the basis of both effectiveness and tolerability. If
glycemic control is not achieved on GLUCOPHAGE XR 2000 mg once daily, a trial of
GLUCOPHAGE XR 1000 mg twice daily should be considered. If higher doses of metformin
are required, GLUCOPHAGE should be used at total daily doses up to 2550 mg administered in
divided daily doses, as described above. (See CLINICAL PHARMACOLOGY: Clinical
Studies.)
Patients receiving GLUCOPHAGE treatment may be safely switched to GLUCOPHAGE XR
once daily at the same total daily dose, up to 2000 mg once daily. Following a switch from
GLUCOPHAGE to GLUCOPHAGE XR, glycemic control should be closely monitored and
dosage adjustments made accordingly (see CLINICAL PHARMACOLOGY: Clinical
Studies).
Pediatrics
The usual starting dose of GLUCOPHAGE is 500 mg twice a day, given with meals. Dosage
increases should be made in increments of 500 mg weekly up to a maximum of 2000 mg per day,
given in divided doses. The dosage of GLUCOPHAGE must be individualized on the basis of
both effectiveness and tolerability. Safety and effectiveness of GLUCOPHAGE XR in pediatric
patients have not been established.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23653391
Herein, our aim was to examine whether micromolar concentrations of metformin alone could bring about cancer cell death and whether micromolar metformin could increase the cytotoxic effect of commonly used chemotherapies in A2780 and SKOV3 cell lines and primary cultured cancer cells isolated from the peritoneal fluid of patients with advanced ovarian cancer. Our results in cell lines demonstrate that no significant loss of viability or change in cell cycle was observed with micromolar metformin alone; however, we observed cytotoxicity with micromolar metformin in combination with chemotherapy at concentrations where the chemotherapy alone produced no loss in viability.
Substance Class |
Chemical
Created
by
admin
on
Edited
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by
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on
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Record UNII |
9100L32L2N
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Record Status |
Validated (UNII)
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Record Version |
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18.5
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A10BD25
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C1892
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N0000175565
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EU/3/17/1965
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432214
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100000085448
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TRANSPORTER -> SUBSTRATE |
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EXCRETED UNCHANGED |
URINE
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL, PREGNANCY PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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GERIATRIC |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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