Phenformin HCl (ST50409947; D08352; W104144)

Alias: W-104144; ST-50409947; D-08352; W104144; ST50409947; D08352; W 104144; ST 50409947; D 08352; Phenformin Hydrochloride; Phenformin HCl; Meltrol; Dipar; Phenethylbiguanide hydrochloride;
Cat No.:V0247 Purity: ≥98%
Phenformin HCl (ST-50409947; D-08352; W-104144), the hydrochloride salt of phenformin, was a marketed anti-diabetic drug ofthe biguanide class, but was withdrawn from most markets in the late 1970s due to a high risk of lactic acidosis.
Phenformin HCl (ST50409947; D08352; W104144) Chemical Structure CAS No.: 834-28-6
Product category: AMPK
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
1g
5g
10g
25g
50g
Other Sizes

Other Forms of Phenformin HCl (ST50409947; D08352; W104144):

  • Phenformin
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Phenformin HCl (ST-50409947; D-08352; W-104144), the hydrochloride salt of phenformin, was a marketed anti-diabetic drug of the biguanide class, but was withdrawn from most markets in the late 1970s due to a high risk of lactic acidosis. It works as an AMP-activated protein kinase (AMPK) activator to reduce blood glucose levels in people with non-insulin-dependent diabetes mellitus. Inhibiting complex 1 of the mitochondrial respiratory chain and activating AMP-activated protein kinase (AMPK)-dependent signaling are the mechanisms by which phenformin increases insulin sensitivity and reduces insulin resistance.

Biological Activity I Assay Protocols (From Reference)
Targets
AMPK
ln Vitro
Without affecting LKB1 activity, phenformin increases the phosphorylation and activation of AMPKalpha1 and AMPKalpha2. [1] In the isolated heart, phenformin increases AMPK activity and phosphorylation; the increase in AMPK activity is always preceded by and correlated with increased cytosolic [AMP]. [2] In comparison to metformin, phenformin has a 50-fold higher inhibitory potency of mitochondrial complex I. In LKB1 deficient NSCLC cell lines, phenformin strongly induces apoptosis. Increased P-AMPK and P-Raptor levels demonstrate that phenformin at 2 mM similarly induces AMPK signaling. Higher levels of cellular stress brought on by phenformin result in the later induction of P-Ser51 eIF2, its downstream target CHOP, and markers of apoptosis. Following prolonged treatment with phenformin, KLluc mice exhibit a significantly higher rate of survival and therapeutic response.[3] AICAR and phenformin both increase AMPK activity in H441 cells in a dose-dependent manner, with maximal stimulation occurring at 2 mm and 5-10 mm, respectively. Phenformin significantly reduces basal ion transport across H441 monolayers by about 50% compared to controls (measured as short circuit current). AICAR and phenformin both significantly lower amiloride-sensitive transepithelial Na+ transport than controls. Through the activation of AMPK and the inhibition of apical Na+ entry through ENaC and basolateral Na+ extrusion through the Na+,K+-ATPase, phenformin and AICAR inhibit amiloride-sensitive Na+ transport across H441 cells.[4] A tendency for a drop in blood insulin levels is seen in phenformin-treated rats (radioimmunoassay).[5]
ln Vivo
Phenformin also increases levels of P-eIF2α and its target BiP/Grp78 in normal lung as well as in lung tumors of mice.[3]
Enzyme Assay
Total AMPK activity is measured using the method of Dagher et al. AMPK activity is quantified in the resuspended pellet as incorporation of32P 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)2SO4pellet is determined using the Bradford method.
Cell Assay
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).
Animal Protocol
Mice;
References

[1]. Am J Physiol Endocrinol Metab. 2004 Aug;287(2):E310-7.

[2]. Am J Physiol Heart Circ Physiol. 2007 Jul;293(1):H457-66.

[3]. J Exp Med. 1993 Jun 1;177(6):1675-80.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H15N5
Molecular Weight
205.2596
Elemental Analysis
C, 49.69; H, 6.67; Cl, 14.67; N, 28.97
CAS #
834-28-6
Appearance
Solid powder
SMILES
C1=CC=C(C=C1)CCN=C(N)N=C(N)N.Cl
InChi Key
YSUCWSWKRIOILX-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H15N5.ClH/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);1H
Chemical Name
1-(diaminomethylidene)-2-(2-phenylethyl)guanidine;hydrochloride
Synonyms
W-104144; ST-50409947; D-08352; W104144; ST50409947; D08352; W 104144; ST 50409947; D 08352; Phenformin Hydrochloride; Phenformin HCl; Meltrol; Dipar; Phenethylbiguanide hydrochloride;
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~48 mg/mL (~198.6 mM)
Water: ~48 mg/mL (~198.6 mM)
Ethanol: ~12 mg/mL (~49.6 mM)
Solubility (In Vivo)
Chemical Name:1-(diaminomethylidene)-2-(2-phenylethyl)guanidine;hydrochlorideInChi Key:YSUCWSWKRIOILX-UHFFFAOYSA-NInChi Code:InChI=1S/C10H15N5.ClH/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);1HSMILES Code:C1=CC=C(C=C1)CCN=C(N)N=C(N)N.Cl (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.8719 mL 24.3593 mL 48.7187 mL
5 mM 0.9744 mL 4.8719 mL 9.7437 mL
10 mM 0.4872 mL 2.4359 mL 4.8719 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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