| Identification | Back Directory | [Name]
TPPU | [CAS]
1222780-33-7 | [Synonyms]
TPPU
CS-2462
TPPU(CS-2462)
TPPU Exclusive
TPPU >=98% (HPLC)
1-Trifluoromethoxyphenyl-3-(1-propionylpiperidin-4-yl) urea
1-(1-Propionylpiperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea
N-[1-(1-Oxopropyl)-4-piperidinyl]-N′-[4-(trifluoromethoxy)phenyl]-urea
Urea, N-[1-(1-oxopropyl)-4-piperidinyl]-N'-[4-(trifluoromethoxy)phenyl]- | [Molecular Formula]
C16H20F3N3O3 | [MOL File]
1222780-33-7.mol | [Molecular Weight]
359.34 |
| Chemical Properties | Back Directory | [Melting point ]
195-196 °C | [Boiling point ]
448.9±45.0 °C(Predicted) | [density ]
1.31±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble10mg/mL, clear (warmed) | [form ]
powder | [pka]
13.11±0.20(Predicted) | [color ]
white to beige |
| Hazard Information | Back Directory | [Uses]
Soluble epoxide hydrolase (sEH) converts epoxides to their corresponding diols. Inhibitors of sEH have anti-inflammatory, anti-hypertensive, neuroprotective, and cardioprotective effects. TPPU is a potent inhibitor of both human and mouse sEH (IC50 = 3.7 and 2.8 nM, respectively). The pharmacokinetics of this compound are dramatically superior to those of the 1-adamantylurea based inhibitors, like AUDA.[Cayman Chemical] | [Uses]
TPPU has been used as a soluble epoxide hydrolase (SEH) inhibitor to characterize its pharmacokinetic (PK) and pharmacodynamic properties in rodents. It has also been used as a SEH inhibitor to study its effects on 12,13-dihydroxy-9Z-octadecenoic acid (12,13-DiHOME) concentrations in nervous tissues. | [Uses]
TPPU is an epoxide hydrolase inhibitor, which has potential in the reduction of inflammatory pain. | [Biological Activity]
tppu is a potent inhibitor of both human and mouse seh.the soluble epoxide hydrolase (seh) can convert epoxides to the corresponding diols by the catalytic addition of a water molecule. seh is implicated in various disease states for its ability to metabolize fatty acid epoxides such as epoxyeicosatrienoic acids and leukotoxin, important endogenous signaling lipids, to less active dihydroxyeicosatrienoic acids and toxic, proinflammatory leukotoxin diols, respectively. seh inhibitors are of growing interest for therapeutic use since they have been shown to increase the in vivo concentration of eets and other fatty acid epoxides. | [Biochem/physiol Actions]
TPPU is a potent sEH inhibitor (IC50 = 3.7 nM) that has been shown to have very favorable PK attributes in cynomolgus monkeys. sEH converts epoxyeicosatrienoic acids (EETs) to dihydroxyiecosatrienoic acids (DHETs), and sEH inhibitors display anti-inflammatory and anti-atherosclerotic effects. | [in vitro]
tppu was identified as a potent inhibitor of both human and mouse seh with ic50 of 3.7 and 2.8 nm, respectively [1]. | [in vivo]
animal study found that oral administration of 13 1-aryl-3-(1-acylpiperidin-4-yl)urea inhibitors including tppu in mice showed substantial improvements in pharmacokinetic parameters over previously reported 1-adamantylurea based inhibitors. for example, 1-(1-(cyclopropanecarbonyl)piperidin-4-yl)-3-(4-(trifluoromethoxy)phenyl)urea, a close analog of tppu, had a 7-fold increase in potency, a 65-fold increase in cmax, and a 3300-fold increase in auc over its adamantine analogue 1-(1-adamantyl)-3-(1-propionylpiperidin-4-yl)urea. this seh inhibitor displayed a 1000-fold increase in potency when compared to morphine by reducing hyperalgesia using the in vivo carrageenan induced inflammatory pain model [1]. | [IC 50]
human and mouse seh (ic50 = 3.7 and 2.8 nm, respectively) | [storage]
Store at -20°C | [References]
[1] rose, t. e.,morisseau, c.,liu, j.y., et al. 1-aryl-3-(1-acylpiperidin-4-yl)urea inhibitors of human and murine soluble epoxide hydrolase: structure-activity relationships, pharmacokinetics, and reduction of inflammatory pain. j med chem. 2010 oct 14;53(19):7067-75. |
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Sigma-Aldrich
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Twochem Co.Ltd.
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