Phenformin

Phenformin

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	A10BA01 (WHO)
Identifiers
IUPAC name 2-(N-phenethylcarbamimidoyl)guanidine
CAS Number	114-86-3 Y
PubChem CID	8249
DrugBank	DB00914 Y
ChemSpider	7953 Y
UNII	DD5K7529CE
KEGG	D08351 Y
ChEBI	CHEBI:8064 N
ChEMBL	ChEMBL170988 Y
CompTox Dashboard (EPA)	DTXSID1023449
ECHA InfoCard	100.003.689
Chemical and physical data
Formula	C10H15N5
Molar mass	205.265 g·mol−1
3D model (JSmol)	Interactive image
Melting point	175 to 178 °C (347 to 352 °F)
SMILES N(=C(/N=C(\N)N)N)\CCc1ccccc1
InChI InChI=1S/C10H15N5/c11-9(12)15-10(13)14-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H6,11,12,13,14,15) Y Key:ICFJFFQQTFMIBG-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Phenformin is an antidiabetic drug from the biguanide class. It was marketed as DBI by Ciba-Geigy, but was withdrawn from most markets in the late 1970s due to a high risk of lactic acidosis, which was fatal in 50% of cases.

Phenformin was developed in 1957 by Ungar, Freedman and Seymour Shapiro, working for the US Vitamin Corporation. Clinical trials begun in 1958 showed it to be effective, but with gastrointestinal side effects.^[1]