5938. Metformin

Nomenclature

CAS number: 657-24-9
N,N-Dimethylimidodicarbonimidic diamide; 1,1-dimethylbiguanide; N,N-dimethyldiguanide; N′-dimethylguanylguanidine; DMGG; LA-6023.
C4H11N5; mol wt 129.16.
C 37.20%, H 8.58%, N 54.22%.

Description and references

Oral hypoglycemic agent. Prepn: Werner, Bell, J. Chem. Soc. 121, 1790 (1922); Shapiro et al., J. Am. Chem. Soc. 81, 3728 (1959). Use as antidiabetic: J. J. Sterne, US 3174901 (1965 to Jan Marcel Didier Aron-Samuel). Toxicity: Rx Bulletin 3, 25 (1972). Determn in plasma: S. AbuRuz et al., J. Chromatogr. B 798, 203 (2003). Clinical pharmacokinetics: G. T. Tucker et al., Br. J. Clin. Pharmacol. 12, 235 (1981). Review of pharmacology: L. S. Hermann, Diabete Metab. 5, 233-245 (1979). Metabolic effects and mechanism of action study: M. Stumvoll et al., N. Engl. J. Med. 333, 550 (1995). Review of efficacy in polycystic ovary syndrome: J. M. Lord et al., Br. Med. J. 327, 951-955 (2003); in type 2 diabetes mellitus: S. M. Setter et al., Clin. Ther. 25, 2991-3026 (2003).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 1115-70-4
Debeone (Armstrong); Diabex (Merck KGaA); Glucophage (Merck KGaA); Metiguanide (Novo).
C4H11N5.HCl; mol wt 165.62.
C 29.01%, H 7.30%, N 42.29%, Cl 21.41%.

Properties

Prisms from water, mp 232° (Werner, Bell); crystals from propanol, mp 218-220° (uncorr) (Shapiro). Sol in water, 95% alcohol. Practically insol in ether, chloroform. LD50 in rats (mg/kg): 1000 orally, 300 s.c. (Rx Bulletin).

Derivative

p-Chlorophenoxyacetate (salt).

Nomenclature

CAS number: 25672-33-7
Glucinan (Merck KGaA).
C4H11N5.C8H7ClO3; mol wt 315.76.
C 45.64%, H 5.75%, N 22.18%, Cl 11.23%, O 15.20%.

Derivative

Embonate.

Nomenclature

CAS number: 34461-22-8
Metformin pamoate; Stagid (Merck KGaA).
(C4H11N5)2.C23H16O6; mol wt 646.70.
C 57.57%, H 5.92%, N 21.66%, O 14.84%.

Therapeutic Category

Antidiabetic. In treatment of polycystic ovary syndrome.

Keywords

Antidiabetic; Biguanides