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P203

Sigma-Aldrich

Phenamil methanesulfonate salt

solid

Synonyme(s) :

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

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About This Item

Formule linéaire :
C12H12ClN7O · CH3SO3H
Numéro CAS:
1161-94-0
Poids moléculaire :
401.83
Numéro MDL:
MFCD00274070
Code UNSPSC :
12352200
ID de substance PubChem :
24277869
Nomenclature NACRES :
NA.77

Forme

solid

Niveau de qualité

100

Couleur

yellow

Solubilité

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

Température de stockage

2-8°C

Chaîne 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)

Clé InChI

MHPIZTURFVSLTJ-UHFFFAOYSA-N

Informations sur le gène

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)

Description générale

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

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
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
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
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%
Kye Won Park et al.
Journal of lipid research, 51(9), 2775-2784 (2010-06-04)
We previously described the use of a cell-based screening approach to identify small molecules that regulate adipocyte differentiation. Here we identify the amiloride derivative phenamil as an adipogenic compound. Phenamil acutely induces expression of the key transcription factor of adipogenesis
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