metformin   Click here for help

GtoPdb Ligand ID: 4779

Synonyms: Glucophage® | LA-6023
Approved drug PDB Ligand Immunopharmacology Ligand
metformin is an approved drug (FDA (1995))
Compound class: Synthetic organic
Comment: Marketed formulations contain metformin hydrochloride (PubChem CID 14219). Metformin is often given in fixed-dose combinations with other antihyperglycemic agents.

Repurposing: Cancer cells undergo a metabolic switch to aerobic glycolysis, and become reliant on this metabolic pathway for energy (the Warburg effect). Inhibition of the glycolytic pathway is therefore considered as a tractable therapeutic target in oncology. As metformin is an inhibitor of glycolysis it is being examined for anti-cancer effects in a number of malignancies. Similarly, it is being examined for anti-inflammatory potential since activated immune cells also undergo a metabolic switch to aerobic glycolysis. If found to be effective, this could ultimately lead to metformin being repurposed for indications other than type 2 diabetes.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 91.49
Molecular weight 129.1
XLogP -0.54
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN(C(=N)N=C(N)N)C
Isomeric SMILES CN(C(=N)N=C(N)N)C
InChI InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
InChI Key XZWYZXLIPXDOLR-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1995))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
1-[(diaminomethylidene)amino]-N,N-dimethylmethanimidamide
International Nonproprietary Names Click here for help
INN number INN
965 metformin
Synonyms Click here for help
Glucophage® | LA-6023
Database Links Click here for help
CAS Registry No. 657-24-9
ChEBI CHEBI:6801
ChEMBL Ligand CHEMBL1431
DrugBank Ligand DB00331
DrugCentral Ligand 1725
GtoPdb PubChem SID 178101481
PubChem CID 4091
RCSB PDB Ligand MF8
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Wikipedia Metformin