4HBP
Target information
- RCSB PDB
- 4HBP
- Title
- Crystal Structure of FAAH in complex with inhibitor
- Method
- X-RAY DIFFRACTION
- Resolution
- 2.91
- Classification
- HYDROLASE/HYDROLASE INHIBITOR
- Organism
- Rattus norvegicus
- Protein
- Fatty-acid amide hydrolase 1 (P97612) Looking for covalent inhibitors of this target ?
- Year
- 2012
- Publication Title
- Synthesis, SAR study, and biological evaluation of a series of piperazine ureas as fatty acid amide hydrolase (FAAH) inhibitors.
- Abstract
-
A series of piperazine ureas was designed, synthesized, and evaluated for their potential as novel orally available fatty acid amide hydrolase (FAAH) inhibitors that are therapeutically effective against pain. We carried out an optimization study of the lead compound 3 to improve its DMPK profile as well as in vitro potency. We identified the thiazole compound 60j with potent inhibitory activity, high brain permeability, and good bioavailability. Compound 60j showed a potent and dose-dependent anti-nociceptive effect in the acetic acid-induced writhing test in mice.
- External Link
- RCSB PDB
Ligand information
- HET
- 17J
- Chain ID
- A
- HET Number
- 600
- Molecular Formula
- C18H18N6OS
- Structure
-
- IUPAC Name
- 4-(3-phenyl-1,2,4-thiadiazol-5-yl)-N-(3-pyridyl)piperazine-1-carboxamide
- InChI
- InChI=1S/C18H18N6OS/c25-17(20-15-7-4-8-19-13-15)23-9-11-24(12-10-23)18-21-16(22-26-18)14-5-2-1-3-6-14/h1-8,13H,9-12H2,(H,20,25)
- InChI Key
- RCAFZHFLIBYWGO-UHFFFAOYSA-N
- Canonical SMILES
- O=C(Nc1cccnc1)N1CCN(c2nc(-c3ccccc3)ns2)CC1
- Bioactivity data
- CI000512
Covalent Binding
- Warhead
- Urea carbonyl
- Reaction Mechanism
- Nucleophilic Substitution
- Residue
- SER : 241
- Residue Chain
- A
- Interactions
- Pharmacophore Model