Phenformin (CED0004599)

Record Information
Version1.0
Creation Date2016-05-25 18:23:37 UTC
Update Date2026-08-18 01:30:57 UTC
Accession NumberCHEM022201
Identification
Common NamePhenformin
ClassSmall Molecule
Description
Phenformin is an organic nitrogen compound with the chemical formula C10H15N5 and an average molecular weight of 205.26 g/mol. Phenformin belongs to the guanidines, a subclass of organonitrogen compounds within the organic compounds. This compound is associated with 16 recorded sources. Within the category of electrical and electronic equipment, it is found in antennas, amplifiers, colour television systems, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials, among eight other sources. In the realm of household cleaning and consumer products, it is released from pipe accessories and bleaching agents. Additionally, it is found in food preservation within the category of food, food processing, and cookware. At the molecular level, phenformin interacts with four recorded protein targets. It acts as an activator or inhibitor of the 5'-AMP-activated protein kinase catalytic subunit alpha-1 (PRKAA1). It also targets the 5'-AMP-activated protein kinase subunit beta-1 (PRKAB1), the 5'-AMP-activated protein kinase subunit gamma-1 (PRKAG1), and the ATP-sensitive inward rectifier potassium channel 8 (KCNJ8).
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
DBIChEBI
FenforminaChEBI
PhenformineChEBI
PhenforminumChEBI
beta-PebgHMDB
beta-PhenethybiguanideHMDB
beta-PhenethylbiguanideHMDB
FenforminHMDB
N-Phenethylbiguanide hydrochlorideHMDB
PEDGHMDB
Phenethylbiguanide hydrochlorideHMDB
PhenethyldiguanideHMDB
Phenformin HCLHMDB
Phenformin hydrochlorideHMDB
Phenformine HCLHMDB
Phenoformine hydrochlorideHMDB
PhenylethylbiguanideHMDB
Chemical FormulaC10H15N5
Average Molecular Mass205.260 g/mol
Monoisotopic Mass205.133 g/mol
CAS Registry Number114-86-3
IUPAC Name1-carbamimidamido-N-(2-phenylethyl)methanimidamide
Traditional Namephenethylbiguanide
SMILESNC(=N)NC(=N)NCCC1=CC=CC=C1
InChI IdentifierInChI=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)
InChI KeyICFJFFQQTFMIBG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as biguanides. These are organic compounds containing two N-linked guanidines.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentBiguanides
Alternative Parents
Substituents
  • Biguanide
  • Benzenoid
  • Monocyclic benzene moiety
  • Carboximidamide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Imine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP-0.72ALOGPS
logP0.83ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)11.97ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area97.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity80.72 m³·mol⁻¹ChemAxon
Polarizability22.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01ox-9500000000-7aebea06c77102624638Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9400000000-2d44b89cb35caa8af343Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9200000000-84c6ee46a948d9683d21Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-4090000000-5c08dc77a8ac5fd63decNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-08fr-9160000000-ca1343aa62b10814e8cdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-08fr-9600000000-5ec2ed0dee0ef942d15cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-08fr-9500000000-313e09ee1de7b1248635Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-08fr-9160000000-b3cdd4f6083050612a03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9300000000-2d44b89cb35caa8af343Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-4890000000-b88f4fe8b0b311cf8c17Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08fr-4900000000-41c5dc8a4d45a1c0e6a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-114l-9600000000-ee92cef524c70103d29bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3920000000-7e451374685fe10f76c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0h90-4900000000-532805a64addc685b93cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-9300000000-85a7cc68d5a3c3790ab6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1290000000-cc97f925ae19c10ad8c2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4900000000-d7923d1935590026b497Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9600000000-b122e284c40b1ce21dd5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w29-1690000000-cd872022fe30b41c7d30Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9310000000-4ae82fa61b7ad3d18992Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-11fec908bf9434b85d4eNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
657.0Log mg/kg[370:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)190.575
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)399.133
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)1031.04
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)298.863
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)253.944
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)139.272
Neutrophil collagenase structureClick to view 3D structureNeutrophil collagenaseP22894HumansPredicted (SEA)245.926
Histamine H2 receptor structureClick to view 3D structureHistamine H2 receptorP25021HumansPredicted (SEA)178.119
Glutamate receptor ionotropic, NMDA 2B structureClick to view 3D structureGlutamate receptor ionotropic, NMDA 2BQ13224HumansPredicted (SEA)36.2777
Click to view 3D structureNeuropeptide FF receptor 2Q9Y5X5HumansPredicted (SEA)180.065
Click to view 3D structureNeuropeptide FF receptor 1Q9GZQ6HumansPredicted (SEA)170.256
Coagulation factor X structureClick to view 3D structureCoagulation factor XP00742HumansPredicted (SEA)313.032
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)276.52
Click to view 3D structureSigma non-opioid intracellular receptor 1Q60492Cavia porcellusPredicted (SEA)312.565
Sodium channel protein type 5 subunit alpha structureClick to view 3D structureSodium channel protein type 5 subunit alphaQ14524HumansPredicted (SEA)165.975
Phospholipase A and acyltransferase 4 structureClick to view 3D structurePhospholipase A and acyltransferase 4Q9UL19HumansPredicted (SEA)2.17978
Click to view 3D structurePhospholipase A and acyltransferase 5Q96KN8HumansPredicted (SEA)2.17978
Phospholipase A and acyltransferase 3 structureClick to view 3D structurePhospholipase A and acyltransferase 3P53816HumansPredicted (SEA)2.17978
Phospholipase A and acyltransferase 2 structureClick to view 3D structurePhospholipase A and acyltransferase 2Q9NWW9HumansPredicted (SEA)2.17978
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)9.26406
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)182.946
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)159.435
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)438.525
Click to view 3D structureMethionine--tRNA ligaseA0A3N3ZFK4Enterococcus faecalisPredicted (SEA)1.47914
Click to view 3D structureMethionine--tRNA ligaseP67578Staphylococcus aureus (strain Mu50 / ATCC 700699)Predicted (SEA)1.47914
Concentrations
Not Available
External Links
DrugBank IDDB00914
HMDB IDHMDB0015050
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPhenformin
Chemspider ID7953
ChEBI ID8064
PubChem Compound ID8249
Kegg Compound IDC07673
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Rosand J, Friedberg JW, Yang JM: Fatal phenformin-associated lactic acidosis. Ann Intern Med. 1997 Jul 15;127(2):170.
2. Enia G, Garozzo M, Zoccali C: Lactic acidosis induced by phenformin is still a public health problem in Italy. BMJ. 1997 Nov 29;315(7120):1466-7.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16567854
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18239244
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20188727
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22036620
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22361631
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23322141
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23475884
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23548904
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23612073