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Details

Stereochemistry ACHIRAL
Molecular Formula C10H15N5.ClH
Molecular Weight 241.721
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENFORMIN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=YSUCWSWKRIOILX-UHFFFAOYSA-N
InChI=1S/C10H15N5.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula C10H15N5
Molecular Weight 205.2596
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
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
On the use of historical control information for trend test in carcinogenesis.
2002 Dec
Response of regimens of insulin therapy in type 2 diabetes mellitus subjects with secondary failure.
2002 May
Enhanced secretion of glucagon-like peptide 1 by biguanide compounds.
2002 Nov 15
A new method for determination of buformin in plasma and urine by ion-paired reversed-phase HPLC with ultraviolet detection.
2002 Oct
[Adverse effect of biguanides].
2002 Sep
Sustaining pattern of phenformin hydrochloride using various polymers and waxes.
2002 Sep-Oct
Insulin and longevity: antidiabetic biguanides as geroprotectors.
2003
At the crossroads: AMP-activated kinase and the LKB1 tumor suppressor link cell proliferation to metabolic regulation.
2003
[A 50-year history of new drugs in Japan-the development and progress of anti-diabetic drugs and the epidemiological aspects of diabetes mellitus].
2003
Complexes between the LKB1 tumor suppressor, STRAD alpha/beta and MO25 alpha/beta are upstream kinases in the AMP-activated protein kinase cascade.
2003
Risk of fatal and nonfatal lactic acidosis with metformin use in type 2 diabetes mellitus.
2003
Involvement of organic cation transporter 1 in the lactic acidosis caused by metformin.
2003 Apr
Antidiabetic and antimalarial biguanide drugs are metal-interactive antiproteolytic agents.
2003 Aug 15
Effects of phenformin on the proliferation of human tumor cell lines.
2003 Dec 19
Should we screen diabetic patients using biguanides for megaloblastic anaemia?
2003 May
Severe acidosis in a patient with type 2 diabetes mellitus, hypertension, and renal failure.
2003 May
Risk of fatal and nonfatal lactic acidosis with metformin use in type 2 diabetes mellitus: systematic review and meta-analysis.
2003 Nov 24
All-cause mortality in diabetic patients treated with combinations of sulfonylureas and biguanides.
2004 Jan-Feb
Rapid and sensitive liquid chromatography-tandem mass spectrometric method for the quantitation of metformin in human plasma.
2004 Sep 5
Metformin transport by renal basolateral organic cation transporter hOCT2.
2005 Feb
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
Deficiency of LKB1 in skeletal muscle prevents AMPK activation and glucose uptake during contraction.
2005 May 18
Identification of potential caloric restriction mimetics by microarray profiling.
2005 Nov 17
Drug-induced pancreatitis: an update.
2005 Sep
Risk of fatal and nonfatal lactic acidosis with metformin use in type 2 diabetes mellitus.
2006 Jan 25
Solid phase extraction--non-aqueous capillary electrophoresis for determination of metformin, phenformin and glyburide in human plasma.
2006 Oct 20
Pharmacological studies on anti-hyperglycemic effect of folium eriobotryae.
2007
The role of AMPK and mTOR in nutrient sensing in pancreatic beta-cells.
2007 Apr 6
The role of mitochondria in protection of the heart by preconditioning.
2007 Aug
Pharmacological activators of AMP-activated protein kinase have different effects on Na+ transport processes across human lung epithelial cells.
2007 Aug
Simultaneous determination of metformin and glipizide in human plasma by liquid chromatography-tandem mass spectrometry.
2007 Feb
Protein kinase CK2 acts as a signal molecule switching between the NDPK-A/AMPK alpha1 complex and NDPK-B.
2007 Jan
Metformin and phenformin activate AMP-activated protein kinase in the heart by increasing cytosolic AMP concentration.
2007 Jul
Simultaneous determination of metformin and rosiglitazone in human plasma by liquid chromatography/tandem mass spectrometry with electrospray ionization: application to a pharmacokinetic study.
2007 Jul 1
Anti-proliferative activity of oral anti-hyperglycemic agents on human vascular smooth muscle cells: thiazolidinediones (glitazones) have enhanced activity under high glucose conditions.
2007 Oct 28
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
Comparison of gene expression changes induced by biguanides in db/db mice liver.
2008 Aug
Mechanisms of myocyte cytotoxicity induced by the multiple receptor tyrosine kinase inhibitor sunitinib.
2008 Dec
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
[Experimental studies on hypoglycemic effects of total flavonoid from Toona sinensis].
2008 Nov
AICAR decreases the activity of two distinct amiloride-sensitive Na+-permeable channels in H441 human lung epithelial cell monolayers.
2008 Nov
Crosstalk between the AMP-activated kinase and insulin signaling pathways rescues murine blastocyst cells from insulin resistance.
2008 Sep
Mechanistic insight into control of CFTR by AMPK.
2009 Feb 27
Are animal models predictive for humans?
2009 Jan 15
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
Mood, side-effects and smoking outcomes among persons with and without probable lifetime depression taking varenicline.
2009 May
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 Fri Dec 15 17:13:45 GMT 2023
Edited
by admin
on Fri Dec 15 17:13:45 GMT 2023
Record UNII
91XC93EU03
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENFORMIN HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
PHENFORMIN HYDROCHLORIDE [MI]
Common Name English
IMIDODICARBONIMIDIC DIAMIDE, N-(2-PHENYLETHYL)-, MONOHYDROCHLORIDE
Common Name English
DEBEI
Brand Name English
NSC-23100
Code English
Phenformin hydrochloride [WHO-DD]
Common Name English
PHENFORMIN HYDROCHLORIDE [MART.]
Common Name English
PHENFORMIN HCL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C98234
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
Code System Code Type Description
MERCK INDEX
m8615
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY Merck Index
RXCUI
235288
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C81696
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
EVMPD
SUB03743MIG
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
SMS_ID
100000085681
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-637-3
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
PUBCHEM
13266
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID0021121
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
DRUG BANK
DBSALT000273
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
NSC
23100
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
CAS
834-28-6
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
FDA UNII
91XC93EU03
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL170988
Created by admin on Fri Dec 15 17:13:45 GMT 2023 , Edited by admin on Fri Dec 15 17:13:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY