P203

Phenamil methanesulfonate salt

PPARγ inducer, solid

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

Properties

• Product Name: Phenamil methanesulfonate salt, solid
• form: solid
• Quality Segment: 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)

Description

General description

Phenamil, a derivative of amiloride is an inhibitor of sodium channels including acid sensing ion channel (ASIC) and epithelial sodium channels (ENaC).[1]

Application

Phenamil methanesulfonate salt has been used:

• to stimulate adipocyte differentiation in 3T3 cells[2]
• to test its effect on lateral flagella expression in Vibrio shilonii[3]
• in nanoparticle preparation to test its effect on osteo/odontoblastic differentiation[4]

Biochem/physiol Actions

Phenamil is an inducer of peroxisome proliferator-activated receptor γ (PPARγ) and inhibits diamine oxidase.[2] By favoring tribbles homolog 3 (Trb3) expression, phenamil holds therapeutic potential to treat pulmonary artery hypertension (PAH) and idiopathic PAH.[1] It is also a bone morphogenetic protein (BMP) activator, which favors osteogenesis and odontogenesis of stem cells.[4]

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)