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915759-45-4

915759-45-4 Structure

915759-45-4 Structure
IdentificationBack Directory
[Name]

BenzenesulfonaMide, 5-(phenylsulfonyl)-N-4-piperidinyl-2-(trifluoroMethyl)-
[CAS]

915759-45-4
[Synonyms]

CS-2786
WAY 316606
WAY-316606
way-316606 /way 316606
WAY-316606;WAY 316606;WAY316606
5-(benzenesulfonyl)-N-piperidin-4-yl-2-(trifluoromethyl)benzenesulfonamide
5-(Phenylsulfonyl)-N-(piperidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide
BenzenesulfonaMide, 5-(phenylsulfonyl)-N-4-piperidinyl-2-(trifluoroMethyl)-
[EINECS(EC#)]

1592732-453-0
[Molecular Formula]

C18H19F3N2O4S2
[MDL Number]

MFCD18206894
[MOL File]

915759-45-4.mol
[Molecular Weight]

448.48
Chemical PropertiesBack Directory
[Boiling point ]

601.1±65.0 °C(Predicted)
[density ]

1.50±0.1 g/cm3(Predicted)
[solubility ]

DMF: 3 mg/ml; DMSO: 3 mg/ml; DMSO:PBS (pH 7.2) (1:10): 0.1 mg/ml
[form ]

Powder
[pka]

8.76±0.20(Predicted)
[color ]

White to off-white
[InChI]

InChI=1S/C18H19F3N2O4S2/c19-18(20,21)16-7-6-15(28(24,25)14-4-2-1-3-5-14)12-17(16)29(26,27)23-13-8-10-22-11-9-13/h1-7,12-13,22-23H,8-11H2
[InChIKey]

ITBGJNVZJBVPLJ-UHFFFAOYSA-N
[SMILES]

C1(S(NC2CCNCC2)(=O)=O)=CC(S(C2=CC=CC=C2)(=O)=O)=CC=C1C(F)(F)F
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Description]

WAY-316606 is an inhibitor of secreted frizzled-related protein 1 (sFRP-1; IC50 = 0.5 μM). It increases Wnt signaling in U2OS osteosarcoma cells (EC50 = 0.65 μM). WAY-316606 increases total bone area in a murine calvarial organ culture assay when used at concentrations greater than 0.1 nM.
[Uses]

WAY 316606 is an inhibitor of the secreted protein sFRP-1, an endogenous antagonist of the secreted glycoprotein Wnt. The affinity of WAY-316606 for sFRP-1 is determined using the FP binding assay with IC50 of 0.5 μM[1].
[Definition]

ChEBI: WAY-316606 is a sulfonamide resulting from the formal condensation of the sulfonic acid group of 5-(phenylsulfonyl)-2-(trifluoromethyl)benzenesulfonic acid with the primary amino group of piperidin-4-amine. An inhibitor of secreted Frizzled-Related Protein-1 (sFRP-1). It has a role as a secreted frizzled-related protein 1 inhibitor. It is a sulfone, a sulfonamide, a member of (trifluoromethyl)benzenes, a member of piperidines and a secondary amino compound.
[in vivo]

WAY-316606 increases bone formation when tested in a neonatal murine calvarial assay. WAY-316606 increases total bone area up to 60% in a dose-dependent manner with an EC50 of about 1 nM. WAY-316606 exhibits moderate to low inhibition of cytochrome p450 isozymes (3A4, 2D6, 2C9) and good stability in rat and human liver microsomes (t1/2>60 min in each species). In female Sprague-Dawley rats, WAY-316606 exhibits high plasma clearance (77 mL/min/kg, greater than hepatic blood flow) following a single intravenous bolus dose (2 mg/kg), which results in a rapid decline of drug exposure in the plasma despite the route of administration[2].

[References]

[1] Moore, WJ, et al. Modulation of Wnt Signaling Through Inhibition of Secreted Frizzled-Related Protein I (sFRP-1) with N-Substituted Piperidinyl Diphenylsulfonyl Sulfonamides. Journal of Medicinal Chemistry (2009), 52(1), 105-116. DOI:10.1021/jm801144h
[2] Bodine PV, et al. A small molecule inhibitor of the Wnt antagonist secreted frizzled-related protein-1 stimulates bone formation. Bone. 2009 Jun;44(6):1063-8. DOI:10.1016/j.bone.2009.02.013
Spectrum DetailBack Directory
[Spectrum Detail]

BenzenesulfonaMide, 5-(phenylsulfonyl)-N-4-piperidinyl-2-(trifluoroMethyl)-(915759-45-4)1HNMR
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