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
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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)
1. Koepsell H. (2013)
The SLC22 family with transporters of organic cations, anions and zwitterions.
Mol Aspects Med, 34 (2-3): 413-35. [PMID:23506881]
2. Lee CF, Lo YC, Cheng CH, Furtmüller GJ, Oh B, Andrade-Oliveira V, Thomas AG, Bowman CE, Slusher BS, Wolfgang MJ et al.. (2015)
Preventing Allograft Rejection by Targeting Immune Metabolism.
Cell Rep, 13 (4): 760-770. [PMID:26489460]
3. Masuda S, Terada T, Yonezawa A, Tanihara Y, Kishimoto K, Katsura T, Ogawa O, Inui K. (2006)
Identification and functional characterization of a new human kidney-specific H+/organic cation antiporter, kidney-specific multidrug and toxin extrusion 2.
J Am Soc Nephrol, 17 (8): 2127-35. [PMID:16807400]
4. Schuiveling M, Vazirpanah N, Radstake TRDJ, Zimmermann M, Broen JCA. (2018)
Metformin, A New Era for an Old Drug in the Treatment of Immune Mediated Disease?.
Curr Drug Targets, 19 (8): 945-959. [PMID:28606032]
5. Shu Y, Sheardown SA, Brown C, Owen RP, Zhang S, Castro RA, Ianculescu AG, Yue L, Lo JC, Burchard EG et al.. (2007)
Effect of genetic variation in the organic cation transporter 1 (OCT1) on metformin action.
J Clin Invest, 117 (5): 1422-31. [PMID:17476361]
6. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K. (2007)
Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters.
Biochem Pharmacol, 74 (2): 359-71. [PMID:17509534]
7. Zhou M, Xia L, Wang J. (2007)
Metformin transport by a newly cloned proton-stimulated organic cation transporter (plasma membrane monoamine transporter) expressed in human intestine.
Drug Metab Dispos, 35 (10): 1956-62. [PMID:17600084]