CAS 834-28-6|Phenformin (hydrochloride)

Introduction：Basic information about CAS 834-28-6|Phenformin (hydrochloride), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Phenformin (hydrochloride) BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles2
8. Synonyms

Common Name	Phenformin (hydrochloride)
CAS Number	834-28-6	Molecular Weight	241.721
Density	1.24 g/cm3	Boiling Point	413.7ºC at 760 mmHg
Molecular Formula	C₁₀H₁₆ClN₅	Melting Point	175-178ºC
MSDS	ChineseUSA	Flash Point	204ºC
Symbol	GHS07	Signal Word	Warning

Names

Name	Phenformin hydrochloride
Synonym	More Synonyms

Phenformin (hydrochloride) BiologicalActivity

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	Signaling Pathways >>Epigenetics >>AMPKSignaling Pathways >>PI3K/Akt/mTOR >>AMPKResearch Areas >>Cancer
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.

Chemical & Physical Properties

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
InChIKey	YSUCWSWKRIOILX-UHFFFAOYSA-N
SMILES	Cl.NC(N)=NC(N)=NCCc1ccccc1
Storage condition	-20°C Freezer
Water Solubility	>=10 g/100 mL at 21 ºC

Toxicological Information

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

Safety Information

Symbol	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

Customs

HS Code	2942000000

Articles2

Hydrogen sulfide mitigates hyperglycemic remodeling via liver kinase B1-adenosine monophosphate-activated protein kinase signaling.

Biochim. Biophys. Acta 1843(12) , 2816-26, (2014)

Hyperglycemia (HG) reduces AMPK activation leading to impaired autophagy and matrix accumulation. Hydrogen sulfide (H2S) treatment improves HG-induced renovascular remodeling however, its mechanism re...

Lactic acidosis treatment by nanomole level of spermidine in an animal model.

Regul Toxicol Pharmacol 70(2) , 514-8, (2014)

Lactic acidosis occurs in a number of clinical conditions, e.g. in surgeries, orthotopic liver transplant, and anesthetic agent administration, which has deleterious effects on the patient's survival....

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

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