Drug Information

General Information
Drug ID
DR00133
Drug Name
Metformin
Synonyms
1,1-Dimethyl biguanide; 1,1-Dimethylbiguanide; 3-(diaminomethylidene)-1,1-dimethylguanidine; DMGG; Diabetosan; Diabex; Diabex (TN); Diaformin (TN); Dianben (TN); Dimethylbiguanide; Dimethylbiguanidine; Dimethyldiguanide; Dimethylguanylguanidine; Fluamine; Flumamine; Fortamet (TN); Gen-Metformin; Glifage; Gliguanid; Glucophage (TN); Glumetza; Glumetza (TN); Glycon; Haurymelin; Islotin; LA-6023; Melbin; Metformin (USAN/INN); Metformin [USAN:INN:BAN]; Metformina; Metformina [DCIT]; Metformina [Spanish]; Metformine; Metformine [INN-French]; Metforminum; Metforminum [INN-Latin]; Metiguanide; N,N-Dimethylbiguanide; N,N-Dimethyldiguanide; N,N-dimethylimidodicarbonimidic diamide; N1,N1-Dimethylbiguanide; NNDG; Nu-Metformin; Obimet (TN); Riomet (TN); Siofor
Drug Type
Small molecular drug
Indication Type 2 diabetes [ICD11:5A11] Approved [1]
Therapeutic Class
Hypoglycemic Agents
Structure
3D MOL 2D MOL
Formula
C4H11N5
Canonical SMILES
CN(C)C(=N)N=C(N)N
InChI
InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
InChIKey
XZWYZXLIPXDOLR-UHFFFAOYSA-N
CAS Number
CAS 657-24-9
Pharmaceutical Properties Molecular Weight 129.16 Topological Polar Surface Area 91.5
Heavy Atom Count 9 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 1
XLogP
-1.3
PubChem CID
4091
PubChem SID
103508547 ,104098198 ,104253645 ,104305401 ,104669488 ,11112469 ,11364723 ,11367285 ,11369847 ,11372888 ,11375447 ,11378011 ,11466032 ,11467152 ,11485664 ,11534102 ,15297229 ,26038962 ,29223200 ,4393083 ,46507752 ,47206702 ,47216870 ,47589085 ,47810852 ,48110542 ,48110543 ,48185089 ,48334597 ,48416229 ,49698302 ,49893836 ,50100453 ,50100454 ,53788989 ,56311366 ,57288471 ,57322135 ,57665782 ,608268 ,76758036 ,7797077 ,7979913 ,81682410 ,85789453 ,89779827 ,92308755 ,93132799 ,93166855 ,9360
ChEBI ID
ChEBI:6801
TTD Drug ID
D0D7LA
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
2-Oct Transporter Info Organic cation transporter 2 Substrate [2]
3-Oct Transporter Info Organic cation transporter 3 Substrate [3]
BCRP Transporter Info Breast cancer resistance protein Substrate [4]
ENT4 Transporter Info Equilibrative nucleoside transporter 4 Substrate [5]
MATE1 Transporter Info Multidrug and toxin extrusion protein 1 Substrate [6]
MATE2 Transporter Info Multidrug and toxin extrusion protein 2 Substrate [7]
THTR1 Transporter Info Thiamine transporter 1 Substrate [8]
THTR2 Transporter Info Thiamine transporter 2 Substrate [8]
Drug-Transporter Activity Data
Drug-Transporter Activity Data 1-Oct Transporter Info Km =2160 microM Chinese hamster ovary (CHO) cells-OCT1 [3]
1-Oct Transporter Info Km =1060 microM Human embryonic kidney cells (HEK293)-OCT1 [9]
1-Oct Transporter Info Km =1470 microM Human embryonic kidney cells (HEK293)-OCT1 [2]
1-Oct Transporter Info Km =5450 microM Human embryonic kidney cells (HEK293)-OCT1 [10]
2-Oct Transporter Info Km =680 microM Human cervical cancer cell line (Hela)-OCT2 [6]
2-Oct Transporter Info Km =990 microM Human embryonic kidney cells (HEK293)-OCT2 [2]
2-Oct Transporter Info Km =1072 microM Human embryonic kidney cells (HEK293)-OCT2 [9]
2-Oct Transporter Info Km =3171 microM Human embryonic kidney cells (HEK293)-OCT2 [11]
2-Oct Transporter Info Km =3356 microM Human embryonic kidney cells (HEK293)-OCT2 [12]
3-Oct Transporter Info Km =2260 microM Chinese hamster ovary (CHO) cells-OCT3 [3]
MATE1 Transporter Info Km =202 microM Human cervical cancer cell line (Hela)-MATE1 [6]
MATE1 Transporter Info Km =227 microM Human embryonic kidney cells (HEK293)-MATE1 [13]
MATE1 Transporter Info Km =780 microM Human embryonic kidney cells (HEK293)-MATE1 [7]
MATE2 Transporter Info Km =1050 microM Human embryonic kidney cells (HEK293)-MATE2K [14]
MATE2 Transporter Info Km =1980 microM Human embryonic kidney cells (HEK293)-MATE2K [7]
THTR2 Transporter Info Km =1150 microM Human embryonic kidney cells-hTHTR2 [8]
References
1 Metformin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Metformin is a superior substrate for renal organic cation transporter OCT2 rather than hepatic OCT1. Drug Metab Pharmacokinet. 2005 Oct;20(5):379-86.
3 Expression of organic cation transporters OCT1 (SLC22A1) and OCT3 (SLC22A3) is affected by genetic factors and cholestasis in human liver. Hepatology. 2009 Oct;50(4):1227-40.
4 Role of human placental apical membrane transporters in the efflux of glyburide, rosiglitazone, and metformin. Am J Obstet Gynecol. 2010 Apr;202(4):383.e1-7.
5 Metformin: from mechanisms of action to therapies. Cell Metab. 2014 Dec 2;20(6):953-66.
6 Human multidrug and toxin extrusion 1 (MATE1/SLC47A1) transporter: functional characterization, interaction with OCT2 (SLC22A2), and single nucleotide polymorphisms. Am J Physiol Renal Physiol. 2010 Apr;298(4):F997-F1005.
7 Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71.
8 Metformin Is a Substrate and Inhibitor of the Human Thiamine Transporter, THTR-2 (SLC19A3). Mol Pharm. 2015 Dec 7;12(12):4301-10.
9 Effects of tetraalkylammonium compounds with different affinities for organic cation transporters on the pharmacokinetics of metformin. Biopharm Drug Dispos. 2007 Dec;28(9):501-10.
10 Genotype-dependent effects of inhibitors of the organic cation transporter, OCT1: predictions of metformin interactions. Pharmacogenomics J. 2011 Dec;11(6):400-11.
11 Functional characterization of the human organic cation transporter 2 variant p.270Ala>Ser. Drug Metab Dispos. 2009 Jun;37(6):1312-8.
12 Structural determinants of inhibitor interaction with the human organic cation transporter OCT2 (SLC22A2). Naunyn Schmiedebergs Arch Pharmacol. 2009 Apr;379(4):337-48.
13 Genetic variants in multidrug and toxic compound extrusion-1, hMATE1, alter transport function. Pharmacogenomics J. 2009 Apr;9(2):127-36.
14 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. 2006 Aug;17(8):2127-35.

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