U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C4H11N5
Molecular Weight 129.1638
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 129.1638
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

7.9418878E11
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
Doses

Doses

DosePopulationAdverse events​
2550 mg 1 times / day steady, oral
Recommended
Dose: 2550 mg, 1 times / day
Route: oral
Route: steady
Dose: 2550 mg, 1 times / day
Sources:
unhealthy, adult
n = 141
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: adult
Population Size: 141
Sources:
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (6%)
Sources:
850 mg 1 times / day steady, oral
Recommended
Dose: 850 mg, 1 times / day
Route: oral
Route: steady
Dose: 850 mg, 1 times / day
Sources:
unhealthy, adult
Disc. AE: Lactic acidosis...
AEs leading to
discontinuation/dose reduction:
Lactic acidosis (grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea 6%
Disc. AE
2550 mg 1 times / day steady, oral
Recommended
Dose: 2550 mg, 1 times / day
Route: oral
Route: steady
Dose: 2550 mg, 1 times / day
Sources:
unhealthy, adult
n = 141
Health Status: unhealthy
Condition: type 2 diabetes mellitus
Age Group: adult
Population Size: 141
Sources:
Lactic acidosis grade 5
Disc. AE
850 mg 1 times / day steady, oral
Recommended
Dose: 850 mg, 1 times / day
Route: oral
Route: steady
Dose: 850 mg, 1 times / day
Sources:
unhealthy, adult
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
Oral hypoglycemic agents: insulin secretagogues, alpha-glucosidase inhibitors and insulin sensitizers.
2001
Metformin, the rebirth of a biguanide: mechanism of action and place in the prevention and treatment of insulin resistance.
2001
Pathogenesis of type 2 diabetes mellitus.
2001
[Type 2 diabetes mellitus: Which place for thiazolidinediones in the therapeutic strategy?].
2001 Apr
[Thiazolidinediones: clinical data and perspectives].
2001 Apr
[Insulin sensitivity and polycystic ovarian syndrome].
2001 Apr
Acute postoperative metabolic complications of diabetes.
2001 Apr
Sulfonylurea treatment of type 2 diabetic patients does not reduce the vasodilator response to ischemia.
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
Prevention of pancreatic cancer induction in hamsters by metformin.
2001 Apr
[Metformin and intravascular contrast media. National guidelines 2001-03-16].
2001 Apr 18
Nateglinide for type 2 diabetes.
2001 Apr 2
[Effects of metformin on insulin resistance and on ovarian steroidogenesis in women with polycystic ovary syndrome].
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
Oral antidiabetic treatment in patients with coronary disease: time-related increased mortality on combined glyburide/metformin therapy over a 7.7-year follow-up.
2001 Feb
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
Cholestatic jaundice associated with the use of metformin.
2001 Jul
Case of the month. Hepatic and renal failure in a patient taking troglitazone and metformin.
2001 Jul
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
Gonadotropins at menopause: the influence of obesity, insulin resistance, and estrogens.
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
Thiazolidinediones and liver toxicity.
2001 Jun
Lactic acidosis in metformin therapy: searching for a link with metformin in reports of 'metformin-associated lactic acidosis'.
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
Safety and efficacy of acarbose in the treatment of Type 2 diabetes: data from a 5-year surveillance study.
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
Cost-effectiveness analysis of intensive blood-glucose control with metformin in overweight patients with type II diabetes (UKPDS No. 51).
2001 Mar
Polycystic ovary syndrome and ovulation induction.
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
Effect of metformin on glucagon-like peptide 1 (GLP-1) and leptin levels in obese nondiabetic subjects.
2001 Mar
[Role and modalities of insulin treatment in type 2 diabetics].
2001 Mar
Improved glycaemic control with miglitol in inadequately-controlled type 2 diabetics.
2001 Mar
[Current and future aspects of oral antidiabetic agents in type 2 diabetes].
2001 May
Cardiomyocyte dysfunction in sucrose-fed rats is associated with insulin resistance.
2001 May
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
[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
[Metformin in the treatment of type 1 diabetics--a placebo controlled study].
2001 May 24
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 Fri Jun 25 23:45:40 UTC 2021
Edited
by admin
on Fri Jun 25 23:45:40 UTC 2021
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 [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
METFORMIN EXTENDED RELEASE
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 Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
LIVERTOX 610
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 18.5
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
WHO-VATC QA10BD07
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
WHO-VATC QA10BD03
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
WHO-ATC A10BD02
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
WHO-VATC QA10BD13
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
WHO-ATC A10BA02
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
WHO-ATC A10BD10
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WHO-ATC A10BD25
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NCI_THESAURUS C1892
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
NDF-RT N0000175565
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
EU-Orphan Drug EU/3/17/1965
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
WHO-VATC QA10BD08
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
WHO-ATC A10BD17
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
WHO-ATC A10BD14
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WHO-ATC A10BD05
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
WHO-VATC QA10BD11
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
WHO-ATC A10BD13
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
WHO-VATC QA10BA02
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WHO-ATC A10BD20
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
FDA ORPHAN DRUG 616117
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
WHO-ATC A10BD11
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
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
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
NCI_THESAURUS C98234
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
NDF-RT N0000007698
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WHO-VATC QA10BD02
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
WHO-VATC QA10BD14
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
WHO-VATC QA10BD10
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WHO-ATC A10BD16
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
FDA ORPHAN DRUG 432214
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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 Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
PUBCHEM
4091
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
PRIMARY
IUPHAR
4779
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
FDA UNII
9100L32L2N
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
EVMPD
SUB08831MIG
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
DRUG BANK
DB00331
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
INN
965
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL1431
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
CAS
657-24-9
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
MESH
D008687
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
NCI_THESAURUS
C61612
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-517-8
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
WIKIPEDIA
METFORMIN
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
PRIMARY
MERCK INDEX
M7280
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY Merck Index
LACTMED
Metformin
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
RXCUI
6809
Created by admin on Fri Jun 25 23:45:41 UTC 2021 , Edited by admin on Fri Jun 25 23:45:41 UTC 2021
PRIMARY RxNorm
EPA CompTox
657-24-9
Created by admin on Fri Jun 25 23:45:40 UTC 2021 , Edited by admin on Fri Jun 25 23:45:40 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> SUBSTRATE
Km
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Vmax
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
EXCRETED UNCHANGED
URINE
SALT/SOLVATE -> PARENT
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