7231. Phenformin

Nomenclature

CAS number: 114-86-3
N-(2-Phenylethyl)imidodicarbonimidic diamide; 1-phenethylbiguanide; phenethyldiguanide; N′-β-phenethylformamidinyliminourea; fenformin; fenormin; β-PEBG; PEDG.
C10H15N5; mol wt 205.26.
C 58.51%, H 7.37%, N 34.12%.

Description and references

Prepn: Shapiro et al., J. Am. Chem. Soc. 81, 2220 (1959); Shapiro, Freedman, US 2961377; US 3057780 (1960, 1962 both to U.S.V.). Metabolism: R. Beckmann, Diabetologia 3, 368 (1967). Association with lactic acidosis in diabetic patients: R. I. Misbin, Ann. Intern. Med. 87, 591 (1977). Toxicity study: G. Proske et al., Arzneim.-Forsch. 12, 314 (1962). Comprehensive description: J. E. Moody, Anal. Profiles Drug Subs. 4, 319-332 (1975). Review of phenformin-induced lactic acidosis: M. E. McGuinness, R. L. Talbert, Ann. Pharmacother. 27, 1183-1187 (1993).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 834-28-6
Insoral (Spofa).
C10H15N5.HCl; mol wt 241.72.
C 49.69%, H 6.67%, N 28.97%, Cl 14.67%.

Properties

Crystals from isopropanol, mp 175-178°. Sol in water; pH (0.1M aq soln): 6.7. LD50 in mice (mg/kg): 19 i.v., 450 orally; in rats: 1050 orally; in guinea pigs: 47 orally, 19 s.c. (Proske).

Therapeutic Category

Antidiabetic.

Keywords

Antidiabetic; Biguanides