EC5026
EC-5026 inhibitor of Epoxide hydrolase developed by EicOsis as investigational new drug (IND) candidate for the management of neuropathic and inflammatory chronic pain and finished phase Ia clinical trial. Related to TPPU
General
Type : Urea derivative, Trifluoro, Piperidine, Drug
Chemical_Nomenclature : 1-[3-fluoro-4-(trifluoromethoxy)phenyl]-3-[1-[(2S)-2-methylbutanoyl]piperidin-4-yl]urea
Canonical SMILES : CCC(C)C(=O)N1CCC(CC1)NC(=O)NC2=CC(=C(C=C2)OC(F)(F)F)F
InChI : InChI=1S\/C18H23F4N3O3\/c1-3-11(2)16(26)25-8-6-12(7-9-25)23-17(27)24-13-4-5-15(14(19)10-13)28-18(20,21)22\/h4-5,10-12H,3,6-9H2,1-2H3,(H2,23,24,27)\/t11-\/m0\/s1
InChIKey : LHRXHTKENPCGSZ-NSHDSACASA-N
Other name(s) : EC-5026 || Q66977824 || (S)-1-(3-Fluoro-4-(trifluoromethoxy)phenyl)-3-(1-(2-methylbutanoyl)piperidin-4-yl)urea
MW : 405.4
Formula : C18H23F4N3O3
CAS_number : 1809885-32-2
PubChem : 91933845
UniChem : LHRXHTKENPCGSZ-NSHDSACASA-N
Target
Families : EC5026 ligand of proteins in family
Epoxide_hydrolase
Protein :
human-EPHX2
References (14)
| 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 : 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 : Enhancing cancer immunotherapy via inhibition of soluble epoxide hydrolase - Kelly_2024_Proc.Natl.Acad.Sci.U.S.A_121_e2314085121 |
| Author(s) : Kelly AG , Wang W , Rothenberger E , Yang J , Gilligan MM , Kipper FC , Attaya A , Gartung A , Hwang SH , Gillespie MJ , Bayer RL , Quinlivan KM , Torres KL , Huang S , Mitsiades N , Yang H , Hammock BD , Panigrahy D |
| Ref : Proc Natl Acad Sci U S A , 121 :e2314085121 , 2024 |
| Abstract : |
| PubMedSearch : Kelly_2024_Proc.Natl.Acad.Sci.U.S.A_121_e2314085121 |
| PubMedID: 38330013 |
| Title : Identification and characterization of the in-vivo metabolites of the novel soluble epoxide hydrolase inhibitor EC5026 using liquid chromatography quadrupole time of flight mass spectrometry - Dey_2024_J.Pharm.Biomed.Anal_244_116116 |
| Author(s) : Dey S , Biradar R , Mane SS , Kunnath Shaji A , Das AP , Agarwal SM , Dengale SJ |
| Ref : J Pharm Biomed Anal , 244 :116116 , 2024 |
| Abstract : |
| PubMedSearch : Dey_2024_J.Pharm.Biomed.Anal_244_116116 |
| PubMedID: 38537542 |
| Title : Enhancing cancer immunotherapy via inhibition of soluble epoxide hydrolase - Kelly_2024_Proc.Natl.Acad.Sci.U.S.A_121_e2314085121 |
| Author(s) : Kelly AG , Wang W , Rothenberger E , Yang J , Gilligan MM , Kipper FC , Attaya A , Gartung A , Hwang SH , Gillespie MJ , Bayer RL , Quinlivan KM , Torres KL , Huang S , Mitsiades N , Yang H , Hammock BD , Panigrahy D |
| Ref : Proc Natl Acad Sci U S A , 121 :e2314085121 , 2024 |
| Abstract : |
| PubMedSearch : Kelly_2024_Proc.Natl.Acad.Sci.U.S.A_121_e2314085121 |
| PubMedID: 38330013 |
| Title : Randomized, double-blind, phase 1a single-ascending dose and food effect studies assessing safety and pharmacokinetics of EC5026 in healthy volunteers - Schmidt_2024_Clin.Transl.Sci_17_e70033 |
| Author(s) : Schmidt WK , Cortes-Puch I , McReynolds CB , Croston GE , Hwang SH , Yang J , Pedersen TL , Wagner KM , Pham TT , Hunt T , Hammock BD |
| Ref : Clin Transl Sci , 17 :e70033 , 2024 |
| Abstract : |
| PubMedSearch : Schmidt_2024_Clin.Transl.Sci_17_e70033 |
| PubMedID: 39300734 |
| Title : Identification and characterization of the in-vivo metabolites of the novel soluble epoxide hydrolase inhibitor EC5026 using liquid chromatography quadrupole time of flight mass spectrometry - Dey_2024_J.Pharm.Biomed.Anal_244_116116 |
| Author(s) : Dey S , Biradar R , Mane SS , Kunnath Shaji A , Das AP , Agarwal SM , Dengale SJ |
| Ref : J Pharm Biomed Anal , 244 :116116 , 2024 |
| Abstract : |
| PubMedSearch : Dey_2024_J.Pharm.Biomed.Anal_244_116116 |
| PubMedID: 38537542 |
| Title : Randomized, double-blind, phase 1a single-ascending dose and food effect studies assessing safety and pharmacokinetics of EC5026 in healthy volunteers - Schmidt_2024_Clin.Transl.Sci_17_e70033 |
| Author(s) : Schmidt WK , Cortes-Puch I , McReynolds CB , Croston GE , Hwang SH , Yang J , Pedersen TL , Wagner KM , Pham TT , Hunt T , Hammock BD |
| Ref : Clin Transl Sci , 17 :e70033 , 2024 |
| Abstract : |
| PubMedSearch : Schmidt_2024_Clin.Transl.Sci_17_e70033 |
| PubMedID: 39300734 |
| Title : How Robust Is the Ligand Binding Transition State? - Bose_2023_J.Am.Chem.Soc__ |
| Author(s) : Bose S , Lotz SD , Deb I , Shuck M , Lee KSS , Dickson A |
| Ref : Journal of the American Chemical Society , : , 2023 |
| Abstract : |
| PubMedSearch : Bose_2023_J.Am.Chem.Soc__ |
| PubMedID: 37943667 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : How Robust Is the Ligand Binding Transition State? - Bose_2023_J.Am.Chem.Soc__ |
| Author(s) : Bose S , Lotz SD , Deb I , Shuck M , Lee KSS , Dickson A |
| Ref : Journal of the American Chemical Society , : , 2023 |
| Abstract : |
| PubMedSearch : Bose_2023_J.Am.Chem.Soc__ |
| PubMedID: 37943667 |
| Gene_locus related to this paper: human-EPHX2 |
| Title : From the Design to the In Vivo Evaluation of Benzohomoadamantane-Derived Soluble Epoxide Hydrolase Inhibitors for the Treatment of Acute Pancreatitis - Codony_2021_J.Med.Chem__ |
| Author(s) : Codony S , Calvo-Tusell C , Valverde E , Osuna S , Morisseau C , Loza MI , Brea J , Perez C , Rodriguez-Franco MI , Pizarro-Delgado J , Corpas R , Grinan-Ferre C , Pallas M , Sanfeliu C , Vazquez-Carrera M , Hammock BD , Feixas F , Vazquez S |
| Ref : Journal of Medicinal Chemistry , : , 2021 |
| Abstract : |
| PubMedSearch : Codony_2021_J.Med.Chem__ |
| PubMedID: 33945278 |
| Title : From the Design to the In Vivo Evaluation of Benzohomoadamantane-Derived Soluble Epoxide Hydrolase Inhibitors for the Treatment of Acute Pancreatitis - Codony_2021_J.Med.Chem__ |
| Author(s) : Codony S , Calvo-Tusell C , Valverde E , Osuna S , Morisseau C , Loza MI , Brea J , Perez C , Rodriguez-Franco MI , Pizarro-Delgado J , Corpas R , Grinan-Ferre C , Pallas M , Sanfeliu C , Vazquez-Carrera M , Hammock BD , Feixas F , Vazquez S |
| Ref : Journal of Medicinal Chemistry , : , 2021 |
| Abstract : |
| PubMedSearch : Codony_2021_J.Med.Chem__ |
| PubMedID: 33945278 |
| Title : Movement to the Clinic of Soluble Epoxide Hydrolase Inhibitor EC5026 as an Analgesic for Neuropathic Pain and for Use as a Nonaddictive Opioid Alternative - Hammock_2021_J.Med.Chem__ |
| Author(s) : Hammock BD , McReynolds CB , Wagner K , Buckpitt A , Cortes-Puch I , Croston G , Lee KSS , Yang J , Schmidt WK , Hwang SH |
| Ref : Journal of Medicinal Chemistry , : , 2021 |
| Abstract : |
| PubMedSearch : Hammock_2021_J.Med.Chem__ |
| PubMedID: 33550801 |
| Title : Movement to the Clinic of Soluble Epoxide Hydrolase Inhibitor EC5026 as an Analgesic for Neuropathic Pain and for Use as a Nonaddictive Opioid Alternative - Hammock_2021_J.Med.Chem__ |
| Author(s) : Hammock BD , McReynolds CB , Wagner K , Buckpitt A , Cortes-Puch I , Croston G , Lee KSS , Yang J , Schmidt WK , Hwang SH |
| Ref : Journal of Medicinal Chemistry , : , 2021 |
| Abstract : |
| PubMedSearch : Hammock_2021_J.Med.Chem__ |
| PubMedID: 33550801 |