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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
Structure of Metformin

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)

HIDE SMILES / InChI

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

Description
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.

Originator

Sources: Werner E.A. and Bell J., J. Chem. Soc. Trans., 1922, 121, 1790 (DOI: 10.1039/CT9222101790)
Curator's Comment: reference retrieved from http://www.rsc.org/images/eic_nov2011_metformin_tcm18-210010.pdf

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
GLUCOPHAGE

Approved Use

Metformin 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 Date

1995
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes
yes
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

PubMed

TitleDatePubMed
Pioglitazone.
2000 Aug
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
Clinical review of glimepiride.
2001 Apr
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
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
ION-pair liquid chromatography technique for the estimation of metformin in its multicomponent dosage forms.
2001 Apr
Metformin-associated lactic acidosis.
2001 Apr
[Metformin and intravascular contrast media. National guidelines 2001-03-16].
2001 Apr 18
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

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
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 Mon Mar 31 17:52:21 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:21 GMT 2025
Record UNII
9100L32L2N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Metformin
INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
METFORMIN EXTENDED RELEASE
Preferred Name English
METFORMIN [VANDF]
Common Name English
METFORMIN [MI]
Common Name English
METFORMIN [USAN]
Common Name English
1,1-Dimethylbiguanide
Systematic Name English
Metformin [WHO-DD]
Common Name English
IMIDODICARBONIMIDIC DIAMIDE, N,N-DIMETHYL-
Systematic Name English
metformin [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QA10BD15
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
LIVERTOX NBK548726
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 18.5
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-VATC QA10BD07
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-VATC QA10BD03
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-ATC A10BD02
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-VATC QA10BD13
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-ATC A10BA02
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-ATC A10BD10
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WHO-ATC A10BD25
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NCI_THESAURUS C1892
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NDF-RT N0000175565
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EU-Orphan Drug EU/3/17/1965
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WHO-VATC QA10BD08
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WHO-ATC A10BD17
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WHO-ATC A10BD14
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WHO-ATC A10BD05
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FDA ORPHAN DRUG 432214
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WHO-VATC QA10BD11
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WHO-ATC A10BD13
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WHO-VATC QA10BA02
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WHO-ATC A10BD20
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
FDA ORPHAN DRUG 616117
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-ATC A10BD11
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
WHO-ATC A10BD22
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WHO-ATC A10BD07
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WHO-ATC A10BD15
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WHO-ATC A10BD03
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WHO-ATC A10BD08
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NCI_THESAURUS C98234
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NDF-RT N0000007698
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WHO-VATC QA10BD02
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WHO-VATC QA10BD14
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WHO-VATC QA10BD10
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WHO-ATC A10BD16
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WHO-VATC QA10BD05
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WHO-ATC A10BD18
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Code System Code Type Description
DRUG CENTRAL
1725
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
PUBCHEM
4091
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
IUPHAR
4779
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
FDA UNII
9100L32L2N
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
EVMPD
SUB08831MIG
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
DRUG BANK
DB00331
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
INN
965
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
ChEMBL
CHEMBL1431
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
CAS
657-24-9
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
DAILYMED
9100L32L2N
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
MESH
D008687
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
NCI_THESAURUS
C61612
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
ECHA (EC/EINECS)
211-517-8
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
WIKIPEDIA
METFORMIN
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
MERCK INDEX
m7280
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY Merck Index
LACTMED
Metformin
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
RXCUI
6809
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID2023270
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
CHEBI
6801
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
SMS_ID
100000085448
Created by admin on Mon Mar 31 17:52:21 GMT 2025 , Edited by admin on Mon Mar 31 17:52:21 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Vmax
EXCRETED UNCHANGED
URINE
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
DERIVATIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL, PREGNANCY
PHARMACOKINETIC
ORAL, RENAL IMPAIRMENT
PHARMACOKINETIC
ORAL, GERIATRIC
PHARMACOKINETIC
ORAL, EXTENDED-RELEASE
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC GERIATRIC

MAXIMUM TOLERATED DOSE TOXICITY FORTAMET

GLUCOPHAGE XR, GLUMETZA

ORAL BIOAVAILABILITY PHARMACOKINETIC