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Details

Stereochemistry ACHIRAL
Molecular Formula C10H15N5
Molecular Weight 205.2596
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENFORMIN

SMILES

NC(=N)NC(=N)NCCC1=CC=CC=C1

InChI

InChIKey=ICFJFFQQTFMIBG-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C10H15N5
Molecular Weight 205.2596
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Phenformin is a biguanide hypoglycemic agent with actions and uses similar to those of metformin. It activates AMP-activated protein kinase (AMPK) and inhibits mTORC1 signaling. Phenformin used for the treatment of diabetes. Phenformin was removed from the U.S. market 20 years ago because of a high incidence of lactic acidosis. Risk factors for the development of lactic acidosis include renal deficiency, hepatic disease, cardiac disease, and drug interaction such as cimetidine. Phenformin exerts potential anti-neoplastic action.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
41.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
INFORMIN
Primary
Unknown

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
100 mg single, oral
PHENFORMIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
81%
100 mg single, oral
PHENFORMIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
200-400 mg bid.
Route of Administration: Oral
In Vitro Use Guide
To evaluate the underlying mechanism of growth inhibition by phenformin, the cell cycle profile was analyzed after treating the SKOV3, Hey and IGROV-1 cell lines with varying doses (0.01-2.5 mM) of phenformin for 24 hours. Phenformin induced G0/G1 cell cycle arrest and reduced S phase in the Hey and SKOV3 OC cell lines and increased G2 phase in the IGROV-1 OC cell line in a dose-dependent manner.
Substance Class Chemical
Record UNII
DD5K7529CE
Record Status Validated (UNII)
Record Version