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P203

Sigma-Aldrich

Phenamil methanesulfonate salt

solid

Synonym(e):

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

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About This Item

Lineare Formel:
C12H12ClN7O · CH3SO3H
CAS-Nummer:
1161-94-0
Molekulargewicht:
401.83
MDL-Nummer:
MFCD00274070
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24277869
NACRES:
NA.77

Form

solid

Qualitätsniveau

100

Farbe

yellow

Löslichkeit

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

Lagertemp.

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)

InChIKey

MHPIZTURFVSLTJ-UHFFFAOYSA-N

Angaben zum 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)

Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (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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