Azucaps;Cronoformin;D Bretard;DB Comb;DB-Retard;DBI;DBI Monohydrochloride;Debeone;Debinyl;Diabis;Dibein;Dibiraf;Dibotin;Dipar;Feguanide;Fenfoduron;Fenormin;Glukopostin;Glyphen;Insoral;Lentobetic;Meltrol;Meltrol-50;Normoglucina;Phenformix;Retardo;

Beta-Pebg;Beta-Phenethybiguanide;Beta-Phenethylbiguanide;Fenformin;Fenformina [INN-Spanish];N-Phenethylbiguanide Hydrochloride;PEDG;Phenethylbiguanide Hydrochloride;Phenethyldiguanide;Phenformin HCl;Phenformin Hydrochloride;Phenformine;Phenformine [INN-French];Phenformine HCl;Phenforminum [INN-Latin];Phenoformine Hydrochloride;Phenylethylbiguanide;

A biguanide hypoglycemic agent with actions and uses similar to those of metformin. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290)

Synthesis Reference	Not Available
General Reference	Enia G, Garozzo M, Zoccali C: Lactic acidosis induced by phenformin is still a public health problem in Italy. BMJ. 1997 Nov 29;315(7120):1466-7. Pubmed Rosand J, Friedberg JW, Yang JM: Fatal phenformin-associated lactic acidosis. Ann Intern Med. 1997 Jul 15;127(2):170. Pubmed

Type	small molecule

Classes

Phenethylamines

Substructures

Benzene and Derivatives Biguanides Phenethylamines Guanidines Aromatic compounds Carboxamidines

Diabetes 糖尿病;

Indication	For the reatment of type II diabetes mellitus.
Pharmacodynamics	Used to treat diabetes, phenformin is a biguanide (contains 2 guanidino groups) hypoglycemic agent with actions and uses similar to those of metformin (Glucophage). Both drugs work by (1) decreasing the absorption of glucose by the intestines, (2) decreasing the production of glucose in the liver, and by (3) increasing the body's ability to use insulin more effectively. More specifically, phenformin improves glycemic control by improving insulin sensitivity. Phenformin is generally considered to be associated with an unacceptably high incidence of actic acidosis. In general biguanides should be used only in stable type II diabetics who are free of liver, kidney and cardiovascular problems and who cannot be controlled with diet.
Mechanism of action	Phenformin binds to the AMP-activated protein kinase (AMPK). AMPK is an ultra-sensitive cellular energy sensor that monitors energy consumption and down-regulates ATP-consuming processes when activated. The biguanide phenformin has been shown to independently decrease ion transport processes, influence cellular metabolism and activate AMPK. Phenformin's hypoglycemic activity is related the effect it has in activating AMPK and fooling insulin sensitive cells into thinking that insulin levels are low and causing the body to use glucose as if in a state of low caloric consumption. This drug also seems to inhibit several varients of ATP-sensitive potassium channels (namely the receptor subtype Kir6.1).
Absorption	Not Available
Volume of distribution	Not Available
Protein binding	Not Available
Metabolism	Not Available
Route of elimination	Not Available
Half life	Not Available
Clearance	Not Available
Toxicity	Not Available
Affected organisms	Humans and other mammals
Pathways	Not Available

Properties
State	solid
Experimental Properties	Property Value Source melting point 176.5 °C PhysProp water solubility 210 mg/mL Not Available logP -0.83 HANSCH,C ET AL. (1995)
Predicted Properties	Property Value Source water solubility 2.32e-01 g/l ALOGPS logP -0.72 ALOGPS logP 0.83 ChemAxon logS -3 ALOGPS pKa (strongest basic) 11.97 ChemAxon physiological charge 2 ChemAxon hydrogen acceptor count 5 ChemAxon hydrogen donor count 5 ChemAxon polar surface area 97.78 ChemAxon rotatable bond count 3 ChemAxon refractivity 80.72 ChemAxon polarizability 22.14 ChemAxon

Not Available