metformin (CHEBI:6801)

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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:CB5320664, eMolecules:2726126, Selleckchem:sn-38, ZINC000004099013

Download	Molfile XML SDF

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Wikipedia	License
SN-38 is an antineoplastic drug. It is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor) but has 1000 times more activity than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold. SN38 is formed via hydrolysis of irinotecan by carboxylesterases and metabolized via glucuronidation by UGT1A1. The variant of UGT1A1 in ~10% of Caucasians which leads to poor metabolism of SN-38 predicts irinotecan toxicity, as it is then less easily excreted from the body in its SN-38 glucuronide form. SN-38 and its glucuronide are lost into the bile and intestines. It can cause the symptoms of diarrhoea and myelosuppression experienced by ~25% of the patients administered irinotecan.
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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.

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

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

Last Modified

26 October 2021

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