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834-28-6

834-28-6 structure
834-28-6 structure
Name Phenformin hydrochloride
Synonyms Phenformin hydrochloride
Phenformini Hydrochloride
Insora
meltrol
phenforminhclno.9113
Imidodicarbonimidic diamide, N-(2-phenylethyl)-, hydrochloride (1:1)
Glucopostin
Phenformine HCL
dbi-td
β-PEBG HCl
DBI monohydrochloride
usafvi-6
MFCD00035039
Phenformin HCl
PhenforMin HCl API
UNII-91XC93EU03
EINECS 212-637-3
Insoral
N-(2-Phenylethyl)imidodicarbonimidic diamide hydrochloride (1:1)
N-Phenethylbiguanide hydrochloride
1-(2-Phenylethyl)biguanide hydrochloride
N'-b-Phenethylformamidinyliminourea Hydrochloride
Phenformin (hydrochloride)
1,1-Benzylmethylbiguanide hydrochloride
Description Phenformin (hydrochloride) is a hydrochloride salt of phenformin that is an anti-diabetic drug from the biguanide class, can activate AMPK activity.
Related Catalog
Target

AMPK

In Vitro Phenformin stimulates the phosphorylation and activation of AMPKalpha1 and AMPKalpha2 without altering LKB1 activity[1]. Phenformin increases AMPK activity and phosphorylation in the isolated heart, the increase in AMPK activity is always preceded by and correlated with increased cytosolic [AMP][2]. Phenformin is a 50-fold more potent inhibitor of mitochondrial complex I than metformin. Phenformin robustly induces apoptosis in LKB1 deficient NSCLC cell lines. Phenformin at 2 mM similarly induces AMPK signaling as shown by increased P-AMPK and P-Raptor levels. Phenformin induces higher levels of cellular stress, triggering induction of P-Ser51 eIF2α and its downstream target CHOP, and markers of apoptosis at later times. Phenformin induces a significant increase in survival and therapeutic response in KLluc mice following long-term treatment[3]. Phenformin and AICAR increases AMPK activity in H441 cells in a dose-dependent fashion, stimulating the kinase maximally at 5-10 mm and 2 mm, respectively. Phenformin significantly decreases basal ion transport (measured as short circuit current) across H441 monolayers by approximately 50% compared with that of controls. Phenformin and AICAR significantly reduce amiloride-sensitive transepithelial Na+ transport compared with controls. Phenformin and AICAR suppress amiloride-sensitive Na+ transport across H441 cells via a pathway that includes activation of AMPK and inhibition of both apical Na+ entry through ENaC and basolateral Na+ extrusion via the Na+,K+-ATPase[4]. Phenformin-treated rats reveals a tendency towards a decrease in blood insulin level (radioimmunoassay)[5].
In Vivo Phenformin increases levels of P-eIF2α and its target BiP/Grp78 in normal lung as well as in lung tumors of mice[3].
Kinase Assay Total AMPK activity is measured using the method of Dagher et al. AMPK activity is quantified in the resuspended pellet as incorporation of 32P from [γ-32P]ATP (10 GBq/mmol) into a synthetic peptide with the specific target sequence for AMPK, the SAMS peptide. Radioactivity is measured using a liquid scintillation counter. Protein content in the solution containing the resupended (NH4)2SO4 pellet is determined using the Bradford method.
References

[1]. Sakamoto K, et al. Activity of LKB1 and AMPK-related kinases in skeletal muscle: effects of contraction, phenformin, and AICAR. Am J Physiol Endocrinol Metab.?2004 Aug;287(2):E310-7.

[2]. Zhang L, et al. Metformin and phenformin activate AMP-activated protein kinase in the heart by increasing cytosolic AMP concentration. Am J Physiol Heart Circ Physiol. 2007 Jul;293(1):H457-66.

[3]. Moreira AL, et al. Thalidomide exerts its inhibitory action on tumor necrosis factor alpha by enhancing mRNA degradation. J Exp Med. 1993 Jun 1;177(6):1675-80.

[4]. Woollhead AM, et al. 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. J Physiol. 2005 Aug 1;566(Pt 3):781-92. Epub 2005

[5]. Dilman VM, et al. Inhibition of DMBA-induced carcinogenesis by phenformin in the mammary gland of rats. Arch Geschwulstforsch. 1978;48(1):1-8.
Density 1.24 g/cm3
Boiling Point 413.7ºC at 760 mmHg
Melting Point 175-178ºC
Molecular Formula C10H16ClN5
Molecular Weight 241.721
Flash Point 204ºC
Exact Mass 241.109421
PSA 97.78000
LogP 2.72010
Storage condition -20°C Freezer
Water Solubility >=10 g/100 mL at 21 ºC

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DU2200000
CHEMICAL NAME :
Biguanide, 1-phenethyl-, monohydrochloride
CAS REGISTRY NUMBER :
834-28-6
LAST UPDATED :
199706
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C10-H15-N5.Cl-H
MOLECULAR WEIGHT :
241.76
WISWESSER LINE NOTATION :
MUYZMYUM&M2R &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
938 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
140 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
17500 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - cyanosis Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
407 mg/kg
TOXIC EFFECTS :
Endocrine - hypoglycemia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
17800 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
47 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
19 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Rodent - rat Liver
DOSE/DURATION :
1 mmol/L
REFERENCE :
EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 24,181,1994
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22
Safety Phrases S36
RIDADR 2811.0
WGK Germany 3
RTECS DU2200000
Hazard Class 6.1
HS Code 2942000000
Precursor  0

DownStream  1

HS Code 2942000000
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