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P203

Phenamil methanesulfonate salt

Name: Phenamil methanesulfonate salt
Brand: SIGMA

PPARγ inducer, solid

Synonym(s):

3,5-Diamino-6-chloro-N-[imino(phenylamino)methyl]pyrazinecarboxamide methanesulfonate salt

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About This Item

Linear Formula:

C₁₂H₁₂ClN₇O · CH₃SO₃H

CAS Number:

1161-94-0

Molecular Weight:

401.83

UNSPSC Code:

12352200

PubChem Substance ID:

24277869

NACRES:

NA.77

MDL number:

MFCD00274070

Form:

solid

Quality level:

100

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Product Name

Phenamil methanesulfonate salt, solid

form

solid

Quality Level

100

color

yellow

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 2.5 mg/mL, DMSO: ≥5 mg/mL (with warming), 0.1 M HCl: insoluble, H₂O: insoluble

storage temp.

2-8°C

SMILES string

CS(O)(=O)=O.Nc1nc(N)c(nc1Cl)C(=O)NC(=N)Nc2ccccc2

InChI

1S/C12H12ClN7O.CH4O3S/c13-8-10(15)19-9(14)7(18-8)11(21)20-12(16)17-6-4-2-1-3-5-6;1-5(2,3)4/h1-5H,(H4,14,15,19)(H3,16,17,20,21);1H3,(H,2,3,4)

InChI key

MHPIZTURFVSLTJ-UHFFFAOYSA-N

Gene Information

human ... SCNN1A(6337), SCNN1B(6338), SCNN1D(6339), SCNN1G(6340)
mouse ... Scnn1a(20276), Scnn1b(20277), Scnn1d(140501), Scnn1g(20278)
rat ... Scnn1a(25122), Scnn1b(24767), Scnn1g(24768)

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

General description

Phenamil, a derivative of amiloride is an inhibitor of sodium channels including acid sensing ion channel (ASIC) and epithelial sodium channels (ENaC).

Application

Phenamil methanesulfonate salt has been used:

to stimulate adipocyte differentiation in 3T3 cells
to test its effect on lateral flagella expression in Vibrio shilonii
in nanoparticle preparation to test its effect on osteo/odontoblastic differentiation

Biochem/physiol Actions

Phenamil is an inducer of peroxisome proliferator-activated receptor γ (PPARγ) and inhibits diamine oxidase. By favoring tribbles homolog 3 (Trb3) expression, phenamil holds therapeutic potential to treat pulmonary artery hypertension (PAH) and idiopathic PAH. It is also a bone morphogenetic protein (BMP) activator, which favors osteogenesis and odontogenesis of stem cells.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Biochemical identification of two types of phenamil binding sites associated with amiloride-sensitive Na+ channels.

P Barbry et al.

Biochemistry, 28(9), 3744-3749 (1989-05-02)

The existence of distinct forms of the epithelium Na+ channel that differ in their sensitivity to amiloride has been repeatedly suggested by physiological data. The biochemical basis for these differences was analyzed by using phenamil, the most potent inhibitor known

Phenamil: an irreversible inhibitor of sodium channels in the toad urinary bladder.

J L Garvin et al.

The Journal of membrane biology, 87(1), 45-54 (1985-01-01)

Several new amiloride analogues and two reported photoaffinity analogues were tested for irreversible inhibition of short-circuit current, Isc, in toad bladder. Bromoamiloride, a photoaffinity analogue, induced 40% irreversible inhibition at 500 microM after irradiation with ultraviolet light greater than or

Induction of the lateral flagellar system of Vibrio shilonii is an early event after inhibition of the sodium ion flux in the polar flagellum.

Yael González et al.

Canadian journal of microbiology, 61(3), 183-191 (2015-02-03)

In this study, we show the induction of lateral flagella by the action of the sodium channel blocker phenamil, in the marine bacterium Vibrio shilonii, a coral pathogen that causes bleaching. We analyzed the growth and morphology of cells treated

The amiloride derivative phenamil attenuates pulmonary vascular remodeling by activating NFAT and the bone morphogenetic protein signaling pathway.

Mun Chun Chan et al.

Molecular and cellular biology, 31(3), 517-530 (2010-12-08)

Pulmonary artery hypertension (PAH) is characterized by elevated pulmonary artery resistance and increased medial thickness due to deregulation of vascular remodeling. Inactivating mutations of the BMPRII gene, which encodes a receptor for bone morphogenetic proteins (BMPs), are identified in ∼60%

Flagellum-mediated motility in Pelotomaculum thermopropionicum SI.

Tomoyuki Kosaka et al.

Bioscience, biotechnology, and biochemistry, 83(7), 1362-1371 (2019-03-29)

The basic functions of a propionate-oxidizing bacterium Pelotomaculum thermopropionicum flagellum, such as motility and chemotaxis, have not been studied. To investigate its motility, we compared with that of Syntrophobacter fumaroxidans, an aflagellar propionate-oxidizing bacterium, in soft agar medium. P. thermopropionicum

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Global Trade Item Number

SKU	GTIN
P203-5MG	04061834357704
P203-25MG	04061832575209

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