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
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)
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 |
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 Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2096907 |
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Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24307270 |
41.0 µM [IC50] | ||
Target ID: CHEMBL2095152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20188727 |
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Target ID: CHEMBL2221341 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20444419 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | INFORMIN Approved UseFor the treatment of type II diabetes mellitus. |
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Primary | Unknown Approved UseUnknown |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1133221/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
81% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1133221/ |
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
Dose | Population | Adverse events |
---|---|---|
2500 mg single, oral Overdose |
healthy n = 1 |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea Sources: Vomiting Anxiety Agitation Polydipsia Polyuria Increased appetite Tachycardia Tachypnea Lactic acidosis Hypoglycemia Hypokalemia |
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
AE | Significance | Dose | Population |
---|---|---|---|
Agitation | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Anxiety | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Hypoglycemia | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Hypokalemia | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Increased appetite | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Lactic acidosis | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Nausea | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Polydipsia | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Polyuria | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Tachycardia | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Tachypnea | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
Vomiting | Disc. AE | 2500 mg single, oral Overdose |
healthy n = 1 |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/23716168/ |
PubMed
Title | Date | PubMed |
---|---|---|
Risk of fatal and nonfatal lactic acidosis with metformin use in type 2 diabetes mellitus. | 2002 |
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Involvement of organic cation transporter 1 in hepatic and intestinal distribution of metformin. | 2002 Aug |
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On the use of historical control information for trend test in carcinogenesis. | 2002 Dec |
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Response of regimens of insulin therapy in type 2 diabetes mellitus subjects with secondary failure. | 2002 May |
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Phenformin suppresses calcium responses to glutamate and protects hippocampal neurons against excitotoxicity. | 2002 May |
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Enhanced secretion of glucagon-like peptide 1 by biguanide compounds. | 2002 Nov 15 |
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A new method for determination of buformin in plasma and urine by ion-paired reversed-phase HPLC with ultraviolet detection. | 2002 Oct |
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[Adverse effect of biguanides]. | 2002 Sep |
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Sustaining pattern of phenformin hydrochloride using various polymers and waxes. | 2002 Sep-Oct |
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Insulin and longevity: antidiabetic biguanides as geroprotectors. | 2003 |
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At the crossroads: AMP-activated kinase and the LKB1 tumor suppressor link cell proliferation to metabolic regulation. | 2003 |
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[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 |
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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 |
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Should we screen diabetic patients using biguanides for megaloblastic anaemia? | 2003 May |
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Severe acidosis in a patient with type 2 diabetes mellitus, hypertension, and renal failure. | 2003 May |
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N-bromosuccinimide-fluorescein based sensitive flow-injection chemiluminescence determination of phenformin. | 2004 Feb |
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Molecularly imprinted solid-phase extraction for the screening of antihyperglycemic biguanides. | 2004 Feb 20 |
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[Lactic acidosis in diabetic patient treated with metformin]. | 2004 Jun |
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The combination of metformin and a dipeptidyl peptidase IV inhibitor prevents 5-fluorouracil-induced reduction of small intestine weight. | 2004 Mar 19 |
|
A convenient five-drug cocktail for the assessment of major drug metabolizing enzymes: a pilot study. | 2004 Sep |
|
Rapid and sensitive liquid chromatography-tandem mass spectrometric method for the quantitation of metformin in human plasma. | 2004 Sep 5 |
|
Phenformin and 5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside (AICAR) activation of AMP-activated protein kinase inhibits transepithelial Na+ transport across H441 lung cells. | 2005 Aug 1 |
|
Contraindications can damage your health--is metformin a case in point? | 2005 Dec |
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Does AMP-activated protein kinase couple inhibition of mitochondrial oxidative phosphorylation by hypoxia to calcium signaling in O2-sensing cells? | 2005 Dec 16 |
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Metformin transport by renal basolateral organic cation transporter hOCT2. | 2005 Feb |
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Effects of phentermine and phenformin on biomarkers of aging in rats. | 2005 Jan-Feb |
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Anti-lipolytic action of AMP-activated protein kinase in rodent adipocytes. | 2005 Jul 1 |
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Deficiency of LKB1 in skeletal muscle prevents AMPK activation and glucose uptake during contraction. | 2005 May 18 |
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Acute renal ischemia rapidly activates the energy sensor AMPK but does not increase phosphorylation of eNOS-Ser1177. | 2005 Nov |
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Identification of potential caloric restriction mimetics by microarray profiling. | 2005 Nov 17 |
|
HIV/AIDS in older adults: a case report and literature review. | 2005 Sep |
|
Drug-induced pancreatitis: an update. | 2005 Sep |
|
[Traditional contraindications to the use of metformin -- more harmful than beneficial?]. | 2006 Jan 20 |
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Solid phase extraction--non-aqueous capillary electrophoresis for determination of metformin, phenformin and glyburide in human plasma. | 2006 Oct 20 |
|
Muscle-specific overexpression of wild type and R225Q mutant AMP-activated protein kinase gamma3-subunit differentially regulates glycogen accumulation. | 2006 Sep |
|
[Diabetic lactic acidosis]. | 2006 Sep 28 |
|
The phase shift hypothesis for the circadian component of winter depression. | 2007 |
|
Pharmacological studies on anti-hyperglycemic effect of folium eriobotryae. | 2007 |
|
Metformin and phenformin activate AMP-activated protein kinase in the heart by increasing cytosolic AMP concentration. | 2007 Jul |
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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 |
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Cellular and molecular mechanisms in the long-term action of antidepressants. | 2008 |
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Complementary regulation of TBC1D1 and AS160 by growth factors, insulin and AMPK activators. | 2008 Jan 15 |
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AICAR decreases the activity of two distinct amiloride-sensitive Na+-permeable channels in H441 human lung epithelial cell monolayers. | 2008 Nov |
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Adenylate kinase and AMP signaling networks: metabolic monitoring, signal communication and body energy sensing. | 2009 Apr 17 |
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High-density lipoprotein modulates glucose metabolism in patients with type 2 diabetes mellitus. | 2009 Apr 21 |
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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 |
|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29245964
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
Edited
Fri Dec 15 15:09:52 GMT 2023
by
admin
on
Fri Dec 15 15:09:52 GMT 2023
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Record UNII |
DD5K7529CE
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QA10BD01
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WHO-ATC |
A10BA01
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NCI_THESAURUS |
C98234
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WHO-VATC |
QA10BA01
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WHO-ATC |
A10BD01
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931
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DB00914
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CHEMBL170988
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PHENFORMIN
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204-057-4
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C81700
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100000082253
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3154
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m8615
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114-86-3
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