Metformin
Title: Metformin
CAS Registry Number: 657-24-9
CAS Name: N,N-Dimethylimidodicarbonimidic diamide
Additional Names: 1,1-dimethylbiguanide; N,N-dimethyldiguanide; N¢-dimethylguanylguanidine; DMGG
Manufacturers' Codes: LA-6023
Molecular Formula: C4H11N5
Molecular Weight: 129.16
Percent Composition: C 37.20%, H 8.58%, N 54.22%
Literature 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).
 
Derivative Type: Hydrochloride
CAS Registry Number: 1115-70-4
Trademarks: Debeone (Armstrong); Diabex (Merck KGaA); Glucophage (Merck KGaA); Metiguanide (Novo)
Molecular Formula: C4H11N5.HCl
Molecular Weight: 165.62
Percent Composition: 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).
Melting point: mp 232° (Werner, Bell); mp 218-220° (uncorr) (Shapiro)
Toxicity data: LD50 in rats (mg/kg): 1000 orally, 300 s.c. (Rx Bulletin)
 
Derivative Type: p-Chlorophenoxyacetate (salt)
CAS Registry Number: 25672-33-7
Trademarks: Glucinan (Merck KGaA)
Molecular Formula: C4H11N5.C8H7ClO3
Molecular Weight: 315.76
Percent Composition: C 45.64%, H 5.75%, N 22.18%, Cl 11.23%, O 15.20%
 
Derivative Type: Embonate
CAS Registry Number: 34461-22-8
Additional Names: Metformin pamoate
Trademarks: Stagid (Merck KGaA)
Molecular Formula: (C4H11N5)2.C23H16O6
Molecular Weight: 646.70
Percent Composition: C 57.57%, H 5.92%, N 21.66%, O 14.84%
 
Therap-Cat: Antidiabetic. In treatment of polycystic ovary syndrome.
Keywords: Antidiabetic; Biguanides.

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