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
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)
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2096907 |
|||
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 |
---|---|---|
Parasitic infections of the gastrointestinal tract. | 2001 Sep |
|
On the use of historical control information for trend test in carcinogenesis. | 2002 Dec |
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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 |
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[Traditional contraindications to the use of metformin -- more harmful than beneficial?]. | 2006 Jan 20 |
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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 |
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Biguanide-induced mitochondrial dysfunction yields increased lactate production and cytotoxicity of aerobically-poised HepG2 cells and human hepatocytes in vitro. | 2008 Dec 1 |
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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 |
|
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 |
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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
Sat Jun 26 11:21:03 UTC 2021
by
admin
on
Sat Jun 26 11:21:03 UTC 2021
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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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SUB09761MIG
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2126
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DD5K7529CE
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C81700
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D010629
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114-86-3
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3154
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M8615
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114-86-3
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