Drug

D0097 | Phenformin

Molecular Formula C10H15N5
Molecular Weight 205.26
Structure
State solid
Description Antidiabetics; biguanide hypoglycemic agent

A

A10BD01 Phenformin and sulfonylureas


[A10BD] Combinations of oral blood glucose lowering drugs


[A10B] BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS


[A10] DRUGS USED IN DIABETES


[A] Alimentary tract and metabolism


A10BA01 Phenformin


[A10BA] Biguanides


[A10B] BLOOD GLUCOSE LOWERING DRUGS, EXCL. INSULINS


[A10] DRUGS USED IN DIABETES


[A] Alimentary tract and metabolism


Toxicity Dose Time Species Model Method Action Positive criterion Reference
TRANSMEMBRANE POTENTIAL 100-300 μM ZDF fa/fa rat & ZDF lean rat isolated liver mitochondria The transmembrane potential of the mitochondria was monitored spectrophotometrically using rhodamine-123. decrease significantly different from control group (p < 0.05) 225
MEMBRANE POTENTIAL 12.5 μM 24 hours human hepatocytes Measurement of mitochondrial membrane potential decrease 15
STATE 2 RESPIRATION 100 nmol/mg mitochondrial protein rat; Sprague–Dawley liver mitochondria Meassurement of respiration decrease 15
STATE 2 RESPIRATION 100 nmol/mg mitochondrial protein 40 minutes preincubation rat; Sprague–Dawley liver mitochondria Meassurement of respiration decrease 15
STATE 3 RESPIRATION 100 nmol/mg mitochondrial protein rat; Sprague–Dawley liver mitochondria Meassurement of respiration decrease 15
STATE 3 RESPIRATION 100 nmol/mg mitochondrial protein 40 min preincubation rat; Sprague–Dawley liver mitochondria Meassurement of respiration decrease 15
RESPIRATORY CONTROL RATIO (RCR) 30-300 μM ZDF fa/fa rat & ZDF lean rat isolated liver mitochondria OCR and measured using a fluorescent oxygen probe (Presens) Negative 225
RESPIRATORY CONTROL RATIO (RCR) 30-300 μM ZDF fa/fa rat & ZDF lean rat isolated liver mitochondria OCR and measured using a fluorescent oxygen probe (Presens) Negative 225
OXYGEN CONSUMPTION RATE (OCR) 25 μM 24 hours human HepG2 cells Measurement of OCR decrease p < 0.001 15
ELECTRON TRANSPORT CHAIN 1.2 mM Bovine heart mitochondria Measurement of complex I activity decrease IC50 15
ELECTRON TRANSPORT CHAIN decrease 35
ELECTRON TRANSPORT CHAIN decrease 43
ELECTRON TRANSPORT CHAIN inhibit 197
ECAR 25 μM 24 hours human HepG2 cells Measurement of ECAR increase p < 0.001 15
GLUCOSE GALACTOSE IC50 RATIO 27 LUHMES (Lund human mesencephalic) cells Glc–Gal–NeuriTox assay EC25(NA) [Glc/Gal] 326
ATP SYNTHESIS 62.5 μM 24 hours human HepG2 cells Assay of Cellular ATP Content decrease p < 0.001 15
ATP SYNTHESIS 62.5 μM 24 hours human HepG2 cells Assay of Cellular ATP Content decrease p < 0.001 15
ATP SYNTHESIS 11.7 μM 24 hours human hepatocytes Assay of Cellular ATP Content decrease IC50 15
ATP SYNTHESIS 12.9 μM 24 hours human HepG2 cells Assay of Cellular ATP Content decrease IC50 15
ATP SYNTHESIS > 500 μM 24 hours human HepG2 cells Assay of Cellular ATP Content decrease IC50 15
OXIDATIVE STRESS 12.5 μM 24 hours human hepatocytes ROS measurement increase 15
OXIDATIVE STRESS 12.5 μM 24 hours human hepatocytes Measurement of mitochondrial membrane potential affect 15

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 1.2 mM Bovine heart mitochondria Measurement of complex I activity inhibitor IC50 15
NADH:ubiquinone reductase inhibitor 35
ATP 62.5 μM 24 hours human HepG2 cells Assay of Cellular ATP Content decrease p < 0.001 15
ATP 62.5 μM 24 hours human HepG2 cells Assay of Cellular ATP Content decrease p < 0.001 15
ATP 11.7 μM 24 hours human hepatocytes Assay of Cellular ATP Content decrease IC50 15
ATP 12.9 μM 24 hours human HepG2 cells Assay of Cellular ATP Content decrease IC50 15
ATP > 500 μM 24 hours human HepG2 cells Assay of Cellular ATP Content decrease IC50 15
Reactive oxygen species 12.5 μM 24 hours human hepatocytes ROS measurement increase 15
oxidized glutathione 12.5 μM 24 hours human hepatocytes Measurement of mitochondrial membrane potential decrease 15

Organism Test type Route Dose (normalized dose) Effect Source
mouse LDLo subcutaneous 200mg/kg (200mg/kg) Journal of the American Chemical Society. Vol. 81, Pg. 3728, 1959.
rat LD50 oral 938mg/kg (938mg/kg) Farmaco, Edizione Scientifica. Vol. 15, Pg. 521, 1960.
guinea pig LD50 subcutaneous 19mg/kg (19mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 314, 1962.
mouse LD50 oral 407mg/kg (407mg/kg) endocrine: hypoglycemia Toxicology and Applied Pharmacology. Vol. 14, Pg. 393, 1969.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg) National Technical Information Service. Vol. AD691-490,
mouse LD50 intravenous 17800ug/kg (17.8mg/kg) U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00094,
guinea pig LD50 oral 47mg/kg (47mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 314, 1962.
rat LD50 intraperitoneal 140mg/kg (140mg/kg) Acta Poloniae Pharmaceutica. For English translation, see APPFAR. Vol. 36, Pg. 401, 1979.
rat LD50 intravenous 17500ug/kg (17.5mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 1571, 1973.


  • .beta.-PEBG .beta.-Phenethylbiguanide 1-(diaminomethylidene)-2-(2-phenylethyl)guanidine
    1-Phenethylbiguanide 1-carbamimidamido-N-(2-phenylethyl)methanimidamide 1-carbamimidoyl-3-phenethyl-guanidine
    114-86-3 2-(N-phenethylcarbamimidoyl)guanidine 4-12-00-02472 (Beilstein Handbook Reference)
    8CV AKOS005567415 ALBB-026048
    API0009066 Azucaps BBL010845
    BDBM50237608 BDBM50240908 BPBio1_000085
    BRD-K11399644-003-03-0 BRN 1977317 BSPBio_000077
    Biguanide, 1-phenethyl- C07673 CAS-834-28-6
    CCRIS 500 CHEBI:8064 CHEMBL170988
    CS-11859 Cronoformin D Bretard
    D08351 DB Comb DB00914
    DD5K7529CE DTXSID1023449 Db-retard
    Debeone Debinyl Diabis
    Dibein Dibiraf Dibotin
    Dipar (Salt/Mix) EINECS 204-057-4 Feguanide
    Fenfoduron Fenformin Fenformina
    Fenformina [INN-Spanish] Fenormin Glukopostin
    Glyphen HMS3604G03 HSDB 3154
    ICFJFFQQTFMIBG-UHFFFAOYSA-N Imidodicarbonimidic diamide, N-(2-phenylethyl)- Imidodicarbonimidic diamide, N-(2-phenylethyl)-, hydrochloride
    Insoral KBio2_002392 KBio2_004960
    KBio2_007528 KBio3_002871 KBioGR_002392
    KBioSS_002397 KS-00000EKW LS-569
    Lentobetic M819 MCULE-1254555434
    MFCD00242966 (95%) MLS006011899 Meltrol (Salt/Mix)
    N''''-[(E)-amino(imino)methyl]-N-(2-phenylethyl)guanidine N''''-{amino[(2-phenylethyl)imino]methyl}guanidine N'-.beta.-Fenetilformamidiniliminourea
    N'-.beta.-Phenethylformamidinylliminourea N'-beta-Fenetilformamidiniliminourea N'-beta-Fenetilformamidiniliminourea [Italian]
    N'-beta-Phenethylformamidinylliminourea N-(2-Phenylethyl)dicarbonimidic diamide # N-(2-Phenylethyl)imidodicarbonimidic diamide
    N-(2-Phenylethyl)triimidodicarbonic diamide N-(2-phenylethyl)imidodicarbonimidic diamide hydrochloride N-(2-phenylethyl)imidodicarbonimidic diamide(Phenformin)
    N-Phenethylbiguanide N-Phenethylbiguanide hydrochloride N-amino(imino)methyl-N-phenethyliminomethanediamine(Phenformin)
    NCGC00016543-01 NCGC00016543-02 NCGC00016543-03
    NCGC00016543-04 NCGC00016543-05 NCGC00016543-08
    NCI-C01741 Normoglucina PHENFORMIN
    PHENFORMIN (SEE ALSO PHENFORMIN HYDROCHLORIDE 834-28-6) Pedg Phenethyldiguanide
    Phenformin (BAN) Phenformin [INN:BAN] Phenformine
    Phenformine HCl Phenformine [INN-French] Phenforminum
    Phenforminum [INN-Latin] Phenformix Phenylethylbiguanide
    Prestwick0_000179 Prestwick1_000179 Prestwick2_000179
    Prestwick3_000179 Q753100 Retardo
    SBB072819 SBI-0206879.P001 SCHEMBL10325620
    SCHEMBL17300524 SCHEMBL8424 SMR004703510
    SPBio_001998 ST45029292 STK635703
    SY031759 TRA0068161 UNII-DD5K7529CE
    W 32 ZINC5851063 amino{imino[(2-phenylethyl)amino]methyl}carboxamidine
    beta-PEBG beta-Phenethybiguanide beta-Phenethylbiguanide
    cMAP_000038

    DrugBank Name Phenformin
    DrugBank DB00914
    CAS Number 114-86-3, 834-28-6
    PubChem Compound 8249
    KEGG Compound ID C07673
    KEGG Drug D08351
    PubChem.Substance 46505230
    ChEBI 8064
    PharmGKB PA1000
    ChemSpider 7953
    BindingDB 50240908.0
    TTD DAP000206
    Wikipedia Phenformin
    HET 8CV

    1. Chan et al. (2005)
    2. Vuda et al. (2016)