Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H4N2O4.C4H11N5 |
Molecular Weight | 285.2599 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)C(=N)NC(N)=N.OC(=O)C1=CC(=O)NC(=O)N1
InChI
InChIKey=KIAVTTZIWJZMIP-UHFFFAOYSA-N
InChI=1S/C5H4N2O4.C4H11N5/c8-3-1-2(4(9)10)6-5(11)7-3;1-9(2)4(7)8-3(5)6/h1H,(H,9,10)(H2,6,7,8,11);1-2H3,(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 |
Molecular Formula | C5H4N2O4 |
Molecular Weight | 156.0963 |
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 |
|||
Target ID: CHEMBL2363065 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22117616 |
|||
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 |
|||
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 hydrochloride in combination with metformin in the treatment of type 2 diabetes mellitus: a randomized, placebo-controlled study. The Pioglitazone 027 Study Group. | 2000 Dec |
|
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 |
|
Clinical review of glimepiride. | 2001 Apr |
|
ION-pair liquid chromatography technique for the estimation of metformin in its multicomponent dosage forms. | 2001 Apr |
|
Lactic acidosis update for critical care clinicians. | 2001 Feb |
|
Increased PAI-1 and tPA antigen levels are reduced with metformin therapy in HIV-infected patients with fat redistribution and insulin resistance. | 2001 Feb |
|
Beta-D-glycosylamidines: potent, selective, and easily accessible 1-glycosidase inhibitors. | 2001 Feb 26 |
|
Diabetes in elderly adults. | 2001 Jan |
|
Continuing metformin throughout pregnancy in women with polycystic ovary syndrome appears to safely reduce first-trimester spontaneous abortion: a pilot study. | 2001 Jan |
|
Oral hypoglycaemic drugs and gastrointestinal symptoms in diabetes mellitus. | 2001 Jan |
|
[Intensified conventional insulin therapy in patients with type 2 diabetes mellitus. Positive long-term effects of insulin lispro on metabolic control and microalbuminuria]. | 2001 Jan 11 |
|
A unique sialidase that cleaves the Neu5Gcalpha2-->5-O(glycolyl)Neu5Gc linkage: comparison of its specificity with that of three microbial sialidases toward four sialic acid dimers. | 2001 Jan 12 |
|
[Severe lactic acidosis due to metformin ingestion in a patient with contra-indication for metformin]. | 2001 Jan 13 |
|
Health care costs associated with escalation of drug treatment in type 2 diabetes mellitus. | 2001 Jan 15 |
|
Pharmacokinetics of metformin gastric-retentive tablets in healthy volunteers. | 2001 Jun |
|
Safety and efficacy of acarbose in the treatment of Type 2 diabetes: data from a 5-year surveillance study. | 2001 Jun |
|
[Metformin and contrast media--increased risk of lactic acidosis?]. | 2001 Jun 10 |
|
Comparison of the metabolic effects of metformin and troglitazone on fructose-induced insulin resistance in male Sprague-Dawley rats. | 2001 Mar |
|
[Role and modalities of insulin treatment in type 2 diabetics]. | 2001 Mar |
|
Accumulation of triglyceride-rich lipoprotein in subjects with abdominal obesity: the biguanides and the prevention of the risk of obesity (BIGPRO) 1 study. | 2001 Mar |
|
Insulin, leptin, IGF-I and insulin-dependent protein concentrations after insulin-sensitizing therapy in obese women with polycystic ovary syndrome. | 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 |
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
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admin
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Edited
Mon Mar 31 19:04:36 GMT 2025
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Record UNII |
KE1D8AP3J5
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Record Status |
Validated (UNII)
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Record Version |
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ACTIVE MOIETY |