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Key Documents

SML0750

Sigma-Aldrich

TPPU

≥98% (HPLC)

Synonym(s):

1-Trifluoromethoxyphenyl-3-(1-propionylpiperidin-4-yl) urea, N-[1-(1-Oxopropyl)-4-piperidinyl]-N′-[4-(trifluoromethoxy)phenyl]-urea

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About This Item

Empirical Formula (Hill Notation):
C16H20F3N3O3
CAS Number:
1222780-33-7
Molecular Weight:
359.34
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear (warmed)

storage temp.

2-8°C

Application

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.

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The oxidized linoleic acid metabolite 12, 13-DiHOME mediates thermal hyperalgesia during inflammatory pain
Zimmer B, et al.
Biochimica et Biophysica Acta - Molecular and Cell Biology of Lipids, 1863(7), 669-678 (2018)
Annika I Ostermann et al.
Prostaglandins & other lipid mediators, 121(Pt A), 131-137 (2015-06-29)
Epoxides from polyunsaturated fatty acids (PUFAs) are potent lipid mediators. In vivo stabilization of these epoxides by blockade of the soluble epoxide hydrolase (sEH) leads to anti-inflammatory, analgesic and normotensive effects. Therefore, sEH inhibitors (sEHi) are a promising new class
Béla Zimmer et al.
Biochimica et biophysica acta. Molecular and cell biology of lipids, 1863(7), 669-678 (2018-04-07)
Eicosanoids play a crucial role in inflammatory pain. However, there is very little knowledge about the contribution of oxidized linoleic acid metabolites in inflammatory pain and peripheral sensitization. Here, we identify 12,13-dihydroxy-9Z-octadecenoic acid (12,13-DiHOME), a cytochrome P450-derived linoleic acid metabolite
Oral treatment of rodents with soluble epoxide hydrolase inhibitor 1-(1-propanoylpiperidin-4-yl)-3-[4-(trifluoromethoxy) phenyl] urea (TPPU): Resulting drug levels and modulation of oxylipin pattern
Ostermann A I, et al.
Prostaglandins & other lipid mediators, 121 (2015)
Qiong Wu et al.
Journal of molecular neuroscience : MN, 67(3), 364-372 (2019-01-16)
High level of corticosterone (CORT) is toxic to neurons and plays an important role in depression-like behavior and chronic stress. Our previous study showed that TPPU, a soluble epoxide hydrolase (sEH) inhibitor (sEHI), induces an antidepressant effect in animal models.
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