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Details

Stereochemistry ACHIRAL
Molecular Formula C10H15N5
Molecular Weight 205.26
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENFORMIN

SMILES

c1ccc(cc1)CCNC(=N)NC(=N)N

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 205.26
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENFORMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
81%
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENFORMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Disc. AE: Nausea, Vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea
Vomiting
Anxiety
Agitation
Polydipsia
Polyuria
Increased appetite
Tachycardia
Tachypnea
Lactic acidosis
Hypoglycemia
Hypokalemia
Sources:
400 mg 2 times / day multiple, oral (max)
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
Disc. AE: Lactic acidosis...
AEs leading to
discontinuation/dose reduction:
Lactic acidosis
Sources:
AEs

AEs

AESignificanceDosePopulation
Agitation Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Anxiety Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Hypoglycemia Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Hypokalemia Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Increased appetite Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Lactic acidosis Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Nausea Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Polydipsia Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Polyuria Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Tachycardia Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Tachypnea Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Vomiting Disc. AE
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy
n = 1
Health Status: healthy
Sex: F
Population Size: 1
Sources:
Lactic acidosis Disc. AE
400 mg 2 times / day multiple, oral (max)
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Type 2 diabetes mellitus
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Parasitic infections of the gastrointestinal tract.
2001 Sep
On the use of historical control information for trend test in carcinogenesis.
2002 Dec
Phenformin suppresses calcium responses to glutamate and protects hippocampal neurons against excitotoxicity.
2002 May
Involvement of organic cation transporter 1 in the lactic acidosis caused by metformin.
2003 Apr
Severe acidosis in a patient with type 2 diabetes mellitus, hypertension, and renal failure.
2003 May
Metformin transport by renal basolateral organic cation transporter hOCT2.
2005 Feb
Metabolic activation of AMP kinase in vascular smooth muscle.
2005 Jan
Effects of phentermine and phenformin on biomarkers of aging in rats.
2005 Jan-Feb
Anti-lipolytic action of AMP-activated protein kinase in rodent adipocytes.
2005 Jul 1
Phenformin-induced lactic acidosis in an older diabetic patient: a recurrent drama (phenformin and lactic acidosis).
2006 Apr
Use of microarray biomarkers to identify longevity therapeutics.
2006 Feb
[Traditional contraindications to the use of metformin -- more harmful than beneficial?].
2006 Jan 20
Risk of fatal and nonfatal lactic acidosis with metformin use in type 2 diabetes mellitus.
2006 Jan 25
AMP-activated protein kinase (AMPK) activating agents cause dephosphorylation of Akt and glycogen synthase kinase-3.
2006 May 28
Simultaneous determination of metformin and glipizide in human plasma by liquid chromatography-tandem mass spectrometry.
2007 Feb
Metformin and phenformin activate AMP-activated protein kinase in the heart by increasing cytosolic AMP concentration.
2007 Jul
Cross-Species Differential Plasma Protein Binding of MBX-102/JNJ39659100: A Novel PPAR-gamma Agonist.
2008
[Cardiovascular risk and cardiometabolic risk: an epidemiological evaluation].
2008 Apr
Dual role of interleukin-6 in regulating insulin sensitivity in murine skeletal muscle.
2008 Dec
Biguanide-induced mitochondrial dysfunction yields increased lactate production and cytotoxicity of aerobically-poised HepG2 cells and human hepatocytes in vitro.
2008 Dec 1
AICAR decreases the activity of two distinct amiloride-sensitive Na+-permeable channels in H441 human lung epithelial cell monolayers.
2008 Nov
AMP-activated protein kinase pathway: a potential therapeutic target in cardiometabolic disease.
2009 Apr
Adenylate kinase and AMP signaling networks: metabolic monitoring, signal communication and body energy sensing.
2009 Apr 17
High-density lipoprotein modulates glucose metabolism in patients with type 2 diabetes mellitus.
2009 Apr 21
Simultaneous determination of anti-diabetes/anti-obesity drugs by LC/PDA, and targeted analysis of sibutramine analog in dietary supplements by LC/MS/MS.
2009 Dec
C-terminal phosphorylation of LKB1 is not required for regulation of AMP-activated protein kinase, BRSK1, BRSK2, or cell cycle arrest.
2009 Jan 2
Regulation of Cl(-) secretion by AMPK in vivo.
2009 Mar
Chemical genomics identifies the unfolded protein response as a target for selective cancer cell killing during glucose deprivation.
2009 May 15
Activation of AMP-activated protein kinase by interleukin-6 in rat skeletal muscle: association with changes in cAMP, energy state, and endogenous fuel mobilization.
2009 Sep
Patents

Sample Use Guides

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
Created
by admin
on Sat Jun 26 11:21:03 UTC 2021
Edited
by admin
on Sat Jun 26 11:21:03 UTC 2021
Record UNII
DD5K7529CE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENFORMIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PHENFORMIN [INN]
Common Name English
PHENFORMIN [MI]
Common Name English
PHENFORMIN [HSDB]
Common Name English
PHENFORMIN [WHO-DD]
Common Name English
IMIDODICARBONIMIDIC DIAMIDE, N-(2-PHENYLETHYL)-
Systematic Name English
PHENFORMIN [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QA10BD01
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
WHO-ATC A10BA01
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
NCI_THESAURUS C98234
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
WHO-VATC QA10BA01
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
WHO-ATC A10BD01
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
Code System Code Type Description
INN
931
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
DRUG BANK
DB00914
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
ChEMBL
CHEMBL170988
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
WIKIPEDIA
PHENFORMIN
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-057-4
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
EVMPD
SUB09761MIG
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
DRUG CENTRAL
2126
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
FDA UNII
DD5K7529CE
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
NCI_THESAURUS
C81700
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
MESH
D010629
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
EPA CompTox
114-86-3
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
PUBCHEM
8249
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
RXCUI
8129
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY RxNorm
HSDB
3154
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
MERCK INDEX
M8615
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY Merck Index
CAS
114-86-3
Created by admin on Sat Jun 26 11:21:04 UTC 2021 , Edited by admin on Sat Jun 26 11:21:04 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
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ACTIVE MOIETY