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P203

Sigma-Aldrich

Phenamil methanesulfonate salt

solid

Sinónimos:

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

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About This Item

Fórmula lineal:
C12H12ClN7O · CH3SO3H
Número de CAS:
1161-94-0
Peso molecular:
401.83
Número MDL:
MFCD00274070
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24277869
NACRES:
NA.77

formulario

solid

Nivel de calidad

100

color

yellow

solubilidad

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

temp. de almacenamiento

2-8°C

cadena SMILES

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)

Clave InChI

MHPIZTURFVSLTJ-UHFFFAOYSA-N

Información sobre el gen

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)

Descripción general

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

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

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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
N Voilley et al.
Proceedings of the National Academy of Sciences of the United States of America, 91(1), 247-251 (1994-01-04)
Water balance in the lung is controlled via active Na+ and Cl- transport. Electrophysiological measurements on lung epithelial cells demonstrated the presence of a Na+ channel that is inhibited by amiloride (K0.5 = 90 nM) and some of its derivatives
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
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
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%
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