TPPU
IC50 23.0 nM
General
Type : Trifluoro, Piperidine, Urea derivative
Chemical_Nomenclature : 1-(1-propanoylpiperidin-4-yl)-3-[4-(trifluoromethoxy)phenyl]urea
Canonical SMILES : CCC(=O)N1CCC(CC1)NC(=O)NC2=CC=C(C=C2)OC(F)(F)F
InChI : InChI=1S\/C16H20F3N3O3\/c1-2-14(23)22-9-7-12(8-10-22)21-15(24)20-11-3-5-13(6-4-11)25-16(17,18)19\/h3-6,12H,2,7-10H2,1H3,(H2,20,21,24)
InChIKey : AAJMQTLFRTZCJK-UHFFFAOYSA-N
Other name(s) : 2RV || CHEMBL1258904 || 4od0 || MLS002415561 || SCHEMBL2719075
MW : 359.34
Formula : C16H20F3N3O3
CAS_number : 1222780-33-7
PubChem : 44142782
UniChem : AAJMQTLFRTZCJK-UHFFFAOYSA-N
Target
Families : TPPU ligand of proteins in family
Epoxide_hydrolase
Structure :
4OD0
Protein :
human-EPHX2
References (28)
| Title : Inhibition of soluble epoxide hydrolase ameliorates cerebral blood flow autoregulation and cognition in alzheimer's disease and diabetes-related dementia rat models - Tang_2025_Geroscience__ |
| Author(s) : Tang C , Border JJ , Zhang H , Gregory A , Bai S , Fang X , Liu Y , Wang S , Hwang SH , Gao W , Morgan GC , Smith J , Bunn D , Cantwell C , Wagner KM , Morisseau C , Yang J , Shin SM , O'Herron P , Bagi Z , Filosa JA , Dong Y , Yu H , Hammock BD , Roman RJ , Fan F |
| Ref : Geroscience , : , 2025 |
| Abstract : |
| PubMedSearch : Tang_2025_Geroscience__ |
| PubMedID: 39903369 |
| Title : Comprehensive single-cell analysis deciphered the immunoregulatory mechanism of TPPU in alleviating sepsis-related acute liver injury - Li_2025_J.Adv.Res__ |
| Author(s) : Li J , Xuan M , Yang L , Liu Y , Lou N , Fu L , Shi Q , Xue C |
| Ref : J Adv Res , : , 2025 |
| Abstract : |
| PubMedSearch : Li_2025_J.Adv.Res__ |
| PubMedID: 39956402 |
| Title : Inhibitors of soluble epoxide hydrolase and cGAS\/STING repair defects in amyloid-beta clearance underlying vascular complications of Alzheimer's disease - Fiala_2025_J.Alzheimers.Dis__13872877241305965 |
| Author(s) : Fiala M , Hammock BD , Hwang SH , Whitelegge J , Paul K , Kaczor-Urbanowicz KE , Urbanowicz A , Kesari S |
| Ref : J Alzheimers Dis , :13872877241305965 , 2025 |
| Abstract : |
| PubMedSearch : Fiala_2025_J.Alzheimers.Dis__13872877241305965 |
| PubMedID: 39962970 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : A Soluble Epoxide Hydrolase Inhibitor Improves Cerebrovascular Dysfunction, Neuroinflammation, Amyloid Burden, and Cognitive Impairments in the hAPP\/PS1 TgF344-AD Rat Model of Alzheimer's Disease - Fang_2025_Int.J.Mol.Sci_26_2433 |
| Author(s) : Fang X , Border JJ , Zhang H , Challagundla L , Kaur J , Hwang SH , Hammock BD , Fan F , Roman RJ |
| Ref : Int J Mol Sci , 26 :2433 , 2025 |
| Abstract : |
| PubMedSearch : Fang_2025_Int.J.Mol.Sci_26_2433 |
| PubMedID: 40141075 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : Inhibiting the soluble epoxide hydrolase increases the EpFAs and ERK1\/2 expression in the hippocampus of LiCl-pilocarpine post-status epilepticus rat model - Peng_2024_IBRO.Neurosci.Rep_17_329 |
| Author(s) : Peng W , Hu Z , Shen Y , Wang X |
| Ref : IBRO Neurosci Rep , 17 :329 , 2024 |
| Abstract : |
| PubMedSearch : Peng_2024_IBRO.Neurosci.Rep_17_329 |
| PubMedID: 39492986 |
| Title : Effects of sEH inhibition on the eicosanoid and cytokine storms in SARS-CoV-2-infected mice - Edin_2024_Faseb.j_38_e23692 |
| Author(s) : Edin ML , Gruzdev A , Graves JP , Lih FB , Morisseau C , Ward JM , Hammock BD , Bosio CM , Zeldin DC |
| Ref : Faseb j , 38 :e23692 , 2024 |
| Abstract : |
| PubMedSearch : Edin_2024_Faseb.j_38_e23692 |
| PubMedID: 38786655 |
| Title : Inhibition of Soluble Epoxide Hydrolase Does Not Promote or Aggravate Pulmonary Hypertension in Rats - Leuillier_2023_Cells_12_ |
| Author(s) : Leuillier M , Platel V , Tu L , Feugray G , Thuillet R , Groussard D , Messaoudi H , Ottaviani M , Chelgham M , Nicol L , Mulder P , Humbert M , Richard V , Morisseau C , Brunel V , Duflot T , Guignabert C , Bellien J |
| Ref : Cells , 12 : , 2023 |
| Abstract : |
| PubMedSearch : Leuillier_2023_Cells_12_ |
| PubMedID: 36831332 |
| Title : Targeting soluble epoxide hydrolase promotes osteogenic-angiogenic coupling via activating SLIT3\/HIF-1alpha signalling pathway - Gao_2023_Cell.Prolif__e13403 |
| Author(s) : Gao L , Chen W , Li L , Li J , Kongling W , Zhang Y , Yang X , Zhao Y , Bai J , Wang F |
| Ref : Cell Prolif , :e13403 , 2023 |
| Abstract : |
| PubMedSearch : Gao_2023_Cell.Prolif__e13403 |
| PubMedID: 36636821 |
| Title : The soluble epoxide hydrolase inhibitor TPPU improves comorbidity of chronic pain and depression via the AHR and TSPO signaling - Luo_2023_J.Transl.Med_21_71 |
| Author(s) : Luo A , Wu Z , Li S , McReynolds CB , Wang D , Liu H , Huang C , He T , Zhang X , Wang Y , Liu C , Hammock BD , Hashimoto K , Yang C |
| Ref : J Transl Med , 21 :71 , 2023 |
| Abstract : |
| PubMedSearch : Luo_2023_J.Transl.Med_21_71 |
| PubMedID: 36732752 |
| Title : TPPU inhibits inflammation-induced excessive autophagy to restore the osteogenic differentiation potential of stem cells and improves alveolar ridge preservation - Dang_2023_Sci.Rep_13_1574 |
| Author(s) : Dang H , Chen W , Chen L , Huo X , Wang F |
| Ref : Sci Rep , 13 :1574 , 2023 |
| Abstract : |
| PubMedSearch : Dang_2023_Sci.Rep_13_1574 |
| PubMedID: 36709403 |
| Title : Soluble epoxide hydrolase inhibitor, TPPU, attenuates progression of atherosclerotic lesions and vascular smooth muscle cell phenotypic switching - Kim_2022_Vascul.Pharmacol__107086 |
| Author(s) : Kim SA , Lee AS , Lee HB , Hur HJ , Lee SH , Sung MJ |
| Ref : Vascul Pharmacol , :107086 , 2022 |
| Abstract : |
| PubMedSearch : Kim_2022_Vascul.Pharmacol__107086 |
| PubMedID: 35752378 |
| Title : Novel aerosol treatment of airway hyper-reactivity and inflammation in a murine model of asthma with a soluble epoxide hydrolase inhibitor - Zhang_2022_PLoS.One_17_e0266608 |
| Author(s) : Zhang C , Li W , Li X , Wan D , Mack S , Zhang J , Wagner K , Wang C , Tan B , Chen J , Wu CW , Tsuji K , Takeuchi M , Chen Z , Hammock BD , Pinkerton KE , Yang J |
| Ref : PLoS ONE , 17 :e0266608 , 2022 |
| Abstract : |
| PubMedSearch : Zhang_2022_PLoS.One_17_e0266608 |
| PubMedID: 35443010 |
| Title : Neuroprotective Epigenetic Changes Induced by Maternal Treatment with an Inhibitor of Soluble Epoxide Hydrolase Prevents Early Alzheimer's Disease Neurodegeneration - Bartra_2022_Int.J.Mol.Sci_23_ |
| Author(s) : Bartra C , Irisarri A , Villoslada A , Corpas R , Aguirre S , Garcia-Lara E , Sunol C , Pallas M , Grinan-Ferre C , Sanfeliu C |
| Ref : Int J Mol Sci , 23 : , 2022 |
| Abstract : |
| PubMedSearch : Bartra_2022_Int.J.Mol.Sci_23_ |
| PubMedID: 36499477 |
| Title : TPPU treatment of burned mice dampens inflammation and generation of bioactive DHET which impairs neutrophil function - Bergmann_2021_Sci.Rep_11_16555 |
| Author(s) : Bergmann CB , Hammock BD , Wan D , Gogolla F , Goetzman H , Caldwell CC , Supp DM |
| Ref : Sci Rep , 11 :16555 , 2021 |
| Abstract : |
| PubMedSearch : Bergmann_2021_Sci.Rep_11_16555 |
| PubMedID: 34400718 |
| Title : 1-trifluoromethoxyphenyl-3(1-propionylpiperidin-4-yl) urea (TPPU), a soluble epoxide hydrolase inhibitor attenuates high fat diet-induced cardiovascular and metabolic disorders in rats - Bukhari_2021_Eur.Rev.Med.Pharmacol.Sci_25_3835 |
| Author(s) : Bukhari IA , Mohamed OY , Mahmood A , Alfadda AA , Almotrefi AA |
| Ref : Eur Rev Med Pharmacol Sci , 25 :3835 , 2021 |
| Abstract : |
| PubMedSearch : Bukhari_2021_Eur.Rev.Med.Pharmacol.Sci_25_3835 |
| PubMedID: 34109592 |
| Title : An epoxide hydrolase inhibitor reduces neuroinflammation in a mouse model of Alzheimer's disease - Ghosh_2020_Sci.Transl.Med_12_ |
| Author(s) : Ghosh A , Comerota MM , Wan D , Chen F , Propson NE , Hwang SH , Hammock BD , Zheng H |
| Ref : Sci Transl Med , 12 : , 2020 |
| Abstract : |
| PubMedSearch : Ghosh_2020_Sci.Transl.Med_12_ |
| PubMedID: 33298560 |
| Title : Soluble epoxide hydrolase inhibitor, TPPU, increases regulatory T cells pathway in an arthritis model - Trindade-da-Silva_2020_FASEB.J__ |
| Author(s) : Trindade-da-Silva CA , Clemente-Napimoga JT , Abdalla HB , Rosa SM , Ueira-Vieira C , Morisseau C , Verri WA, Jr. , Montalli VAM , Hammock BD , Napimoga MH |
| Ref : FASEB Journal , : , 2020 |
| Abstract : |
| PubMedSearch : Trindade-da-Silva_2020_FASEB.J__ |
| PubMedID: 32400048 |
| Title : 1-trifluoromethoxyphenyl-3-(1-propionylpiperidin-4-yl) urea (TPPU), a soluble epoxide hydrolase inhibitor, lowers L-NAME-induced hypertension through suppression of angiotensin-converting enzyme in rats - Bukhari_2020_Eur.Rev.Med.Pharmacol.Sci_24_8143 |
| Author(s) : Bukhari IA , Alorainey BI , Al-Motrefi AA , Mahmoud A , Campbell WB , Hammock BD |
| Ref : Eur Rev Med Pharmacol Sci , 24 :8143 , 2020 |
| Abstract : |
| PubMedSearch : Bukhari_2020_Eur.Rev.Med.Pharmacol.Sci_24_8143 |
| PubMedID: 32767352 |
| Title : TPPU, a sEH Inhibitor, Attenuates Corticosterone-Induced PC12 Cell Injury by Modulation of BDNF-TrkB Pathway - Wu_2019_J.Mol.Neurosci_67_364 |
| Author(s) : Wu Q , Song J , Meng D , Chang Q |
| Ref : Journal of Molecular Neuroscience , 67 :364 , 2019 |
| Abstract : |
| PubMedSearch : Wu_2019_J.Mol.Neurosci_67_364 |
| PubMedID: 30644034 |
| Title : Inhibition of soluble epoxide hydrolase ameliorates hyperhomocysteinemia-induced hepatic steatosis by enhancing beta-oxidation of fatty acid in mice - Yao_2019_Am.J.Physiol.Gastrointest.Liver.Physiol_316_G527 |
| Author(s) : Yao L , Cao B , Cheng Q , Cai W , Ye C , Liang J , Liu W , Tan L , Yan M , Li B , He J , Hwang SH , Zhang X , Wang C , Ai D , Hammock BD , Zhu Y |
| Ref : American Journal of Physiology Gastrointest Liver Physiol , 316 :G527 , 2019 |
| Abstract : |
| PubMedSearch : Yao_2019_Am.J.Physiol.Gastrointest.Liver.Physiol_316_G527 |
| PubMedID: 30789748 |
| Title : 1-Trifluoromethoxyphenyl-3-(1-propionylpiperidin-4-yl) Urea, a Selective and Potent Dual Inhibitor of Soluble Epoxide Hydrolase and p38 Kinase Intervenes in Alzheimer's Signaling in Human Nerve Cells - Liang_2019_ACS.Chem.Neurosci_10_4018 |
| Author(s) : Liang Z , Zhang B , Xu M , Morisseau C , Hwang SH , Hammock BD , Li QX |
| Ref : ACS Chem Neurosci , 10 :4018 , 2019 |
| Abstract : |
| PubMedSearch : Liang_2019_ACS.Chem.Neurosci_10_4018 |
| PubMedID: 31378059 |
| Title : Recent Advances in the Early Intervention in Schizophrenia: Future Direction from Preclinical Findings - Hashimoto_2019_Curr.Psychiatry.Rep_21_75 |
| Author(s) : Hashimoto K |
| Ref : Curr Psychiatry Rep , 21 :75 , 2019 |
| Abstract : |
| PubMedSearch : Hashimoto_2019_Curr.Psychiatry.Rep_21_75 |
| PubMedID: 31278495 |
| Title : An inhibitor of soluble epoxide hydrolase ameliorates diabetes-induced learning and memory impairment in rats - Minaz_2018_Prostaglandins.Other.Lipid.Mediat_136_84 |
| Author(s) : Minaz N , Razdan R , Hammock BD , Goswami SK |
| Ref : Prostaglandins Other Lipid Mediat , 136 :84 , 2018 |
| Abstract : |
| PubMedSearch : Minaz_2018_Prostaglandins.Other.Lipid.Mediat_136_84 |
| PubMedID: 29751149 |
| Title : Soluble epoxide hydrolase inhibitor 1-trifluoromethoxyphenyl-3- (1-propionylpiperidin-4-yl) urea attenuates bleomycin-induced pulmonary fibrosis in mice - Zhou_2016_Cell.Tissue.Res_363_399 |
| Author(s) : Zhou Y , Sun GY , Liu T , Duan JX , Zhou HF , Lee KS , Hammock BD , Fang X , Jiang JX , Guan CX |
| Ref : Cell Tissue Research , 363 :399 , 2016 |
| Abstract : |
| PubMedSearch : Zhou_2016_Cell.Tissue.Res_363_399 |
| PubMedID: 26310139 |
| Title : Anti-Ulcer Efficacy of Soluble Epoxide Hydrolase Inhibitor TPPU on Diclofenac-Induced Intestinal Ulcers - Goswami_2016_J.Pharmacol.Exp.Ther_357_529 |
| Author(s) : Goswami SK , Wan D , Yang J , Trindade da Silva CA , Morisseau C , Kodani SD , Yang GY , Inceoglu B , Hammock BD |
| Ref : Journal of Pharmacology & Experimental Therapeutics , 357 :529 , 2016 |
| Abstract : |
| PubMedSearch : Goswami_2016_J.Pharmacol.Exp.Ther_357_529 |
| PubMedID: 26989141 |
| Title : 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_2015_Prostaglandins.Other.Lipid.Mediat_121_131 |
| Author(s) : Ostermann AI , Herbers J , Willenberg I , Chen R , Hwang SH , Greite R , Morisseau C , Gueler F , Hammock BD , Schebb NH |
| Ref : Prostaglandins Other Lipid Mediat , 121 :131 , 2015 |
| Abstract : |
| PubMedSearch : Ostermann_2015_Prostaglandins.Other.Lipid.Mediat_121_131 |
| PubMedID: 26117215 |
| Title : Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy - Lee_2014_J.Med.Chem_57_7016 |
| Author(s) : Lee KS , Liu JY , Wagner KM , Pakhomova S , Dong H , Morisseau C , Fu SH , Yang J , Wang P , Ulu A , Mate CA , Nguyen LV , Hwang SH , Edin ML , Mara AA , Wulff H , Newcomer ME , Zeldin DC , Hammock BD |
| Ref : Journal of Medicinal Chemistry , 57 :7016 , 2014 |
| Abstract : |
| PubMedSearch : Lee_2014_J.Med.Chem_57_7016 |
| PubMedID: 25079952 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : - |
| Ref : |
| PubMedID: |
| Gene_locus related to this paper: human-EPHX2 |