metformin (CHEBI:6801)

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CHEBI:6801 - metformin

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ChEBI Name	metformin

ChEBI ID	CHEBI:6801

Definition	A member of the class of guanidines that is biguanide the carrying two methyl substituents at position 1.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB22706988, ChemicalBook:CB0506294, eMolecules:26219491, eMolecules:10320221, eMolecules:661910, ZINC000012859773

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

MF8 - Ideal conformer

Mrv1927 06102113323D

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Time for openFile(MF8 - Ideal conformer

Mrv1927 06102113323D

20 19 0 0 0 0 999 V2000

-2.8810 -1.0200 0.0970 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.8880 -0.1850 -0.0180 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5890 -0.6460 0.0420 N 0 0 0 0 0 0 0 0 0 0 0 0

-2.1340 1.1550 -0.2010 N 0 0 0 0 0 0 0 0 0 0 0 0

2.0200 -1.6460 -0.1020 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7550 -0.2080 -0.0090 N 0 0 0 0 0 0 0 0 0 0 0 0

0.2250 1.5270 0.1440 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4610 0.2490 0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8700 0.7430 0.0100 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.7070 -1.9680 0.2040 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9000 1.5700 0.2250 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5410 1.6860 -0.7550 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4130 -1.6000 0.0720 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9630 2.1570 0.1560 H 0 0 0 0 0 0 0 0 0 0 0 0

3.1120 1.0390 -1.0100 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5860 1.6230 0.5870 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7400 0.2730 0.4690 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1200 -2.0630 0.9000 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1940 -2.1350 -0.6190 H 0 0 0 0 0 0 0 0 0 0 0 0

2.9440 -1.8100 -0.6570 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

2 4 1 0 0 0 0

2 3 1 0 0 0 0

3 8 1 0 0 0 0

8 7 2 0 0 0 0

8 6 1 0 0 0 0

6 9 1 0 0 0 0

6 5 1 0 0 0 0

1 10 1 0 0 0 0

4 11 1 0 0 0 0

4 12 1 0 0 0 0

3 13 1 0 0 0 0

7 14 1 0 0 0 0

9 15 1 0 0 0 0

9 16 1 0 0 0 0

9 17 1 0 0 0 0

5 18 1 0 0 0 0

5 19 1 0 0 0 0

5 20 1 0 0 0 0

M END): 21 ms

reading 20 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

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Wikipedia	License
Metformin, sold under the brand name Glucophage, among others, is the main first-line medication for the treatment of type 2 diabetes, particularly in people who are overweight. It is also used in the treatment of polycystic ovary syndrome, and is sometimes used as an off-label adjunct to lessen the risk of metabolic syndrome in people who take antipsychotic medication. It has been shown to inhibit inflammation, and is not associated with weight gain. Metformin is taken by mouth. Metformin is generally well tolerated. Common adverse effects include diarrhea, nausea, and abdominal pain. It has a small risk of causing low blood sugar. High blood lactic acid level (acidosis) is a concern if the medication is used in overly large doses or prescribed in people with severe kidney problems. Metformin is a biguanide anti-hyperglycemic agent. It works by decreasing glucose production in the liver, increasing the insulin sensitivity of body tissues, and increasing GDF15 secretion, which reduces appetite and caloric intake. Metformin was first described in the scientific literature in 1922 by Emil Werner and James Bell. French physician Jean Sterne began the study in humans in the 1950s. It was introduced as a medication in France in 1957. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2022, it was the second most commonly prescribed medication in the United States, with more than 86 million prescriptions. In Australia, it was one of the top 10 most prescribed medications between 2017 and 2023.
Read full article at Wikipedia

Formula

C4H11N5

Net Charge

Average Mass

129.167

Monoisotopic Mass

129.10145

InChI

InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)

InChIKey

XZWYZXLIPXDOLR-UHFFFAOYSA-N

SMILES

CN(C)C(=N)NC(N)=N

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects.

Biological Role(s):	xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.

Application(s):	hypoglycemic agent A drug which lowers the blood glucose level. geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	metformin (CHEBI:6801) has functional parent biguanide (CHEBI:3095) metformin (CHEBI:6801) has role environmental contaminant (CHEBI:78298) metformin (CHEBI:6801) has role geroprotector (CHEBI:176497) metformin (CHEBI:6801) has role hypoglycemic agent (CHEBI:35526) metformin (CHEBI:6801) has role xenobiotic (CHEBI:35703) metformin (CHEBI:6801) is a guanidines (CHEBI:24436) metformin (CHEBI:6801) is conjugate base of metformin(1+) (CHEBI:90688)

Incoming	metformin(1+) (CHEBI:90688) is conjugate acid of metformin (CHEBI:6801)

IUPAC Name

N,N-dimethyltriimidodicarbonic diamide

INNs	Sources
metformin	WHO MedNet
metformina	WHO MedNet
metformine	WHO MedNet
metforminum	WHO MedNet

Synonyms	Sources
1,1-dimethylbiguanide	ChemIDplus
dimethylbiguanide	ChemIDplus
dimethyldiguanide	ChemIDplus
LA 6023	DrugBank
LA-6023	ChemIDplus
N,N-dimethylbiguanide	ChemIDplus
N,N-dimethyldiguanide	ChemIDplus
N,N-dimethylguanylguanidine	DrugCentral
N,N-dimethylimidodicarbonimidic diamide	IUPAC
N¹,N¹-dimethylbiguanide	ChemIDplus

Manual Xrefs	Databases
1725	DrugCentral
C07151	KEGG COMPOUND
D04966	KEGG DRUG
DB00331	DrugBank
FDB022739	FooDB
HMDB0001921	HMDB
LSM-4730	LINCS
Metformin	Wikipedia
MF8	PDBeChem
View more database links

Registry Numbers	Types	Sources
606492	Reaxys Registry Number	Reaxys
657-24-9	CAS Registry Number	ChemIDplus

Citations

Last Modified

26 October 2021

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag

CHEBI:6801 - metformin

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