metformin

Ligand id: 4779

Name: metformin

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Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1995))
IUPAC Name
1-[(diaminomethylidene)amino]-N,N-dimethylmethanimidamide
International Nonproprietary Names
INN number INN
965 metformin
Synonyms
Glucophage® | LA-6023
Comments
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.
Database Links
CAS Registry No. 657-24-9
ChEBI CHEBI:6801
ChEMBL Ligand CHEMBL1431
DrugBank Ligand DB00331
GtoPdb PubChem SID 178101481
PubChem CID 4091
RCSB PDB Ligand MF8
Search Google for chemical match using the InChIKey XZWYZXLIPXDOLR-UHFFFAOYSA-N
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Search PubMed clinical trials metformin
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Search UniChem for chemical match using the InChIKey XZWYZXLIPXDOLR-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone XZWYZXLIPXDOLR
Wikipedia Metformin