| Identification | Back Directory | [Name]
JNJ 1661010 | [CAS]
681136-29-8 | [Synonyms]
CS-1527
Takeda-25
JNJ 1661010
JNJ 1661010, >=98%
JNJ 1661010 USP/EP/BP
TAKEDA-25;JNJ-1661010;JNJ 1661010
N-Phenyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide
N-Phenyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)-1-piperazinecarboxamide
1-Piperazinecarboxamide, N-phenyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)- | [Molecular Formula]
C19H19N5OS | [MDL Number]
MFCD00209157 | [MOL File]
681136-29-8.mol | [Molecular Weight]
365.459 |
| Chemical Properties | Back Directory | [density ]
1.340±0.06 g/cm3(Predicted) | [storage temp. ]
Store at +4°C | [solubility ]
DMSO: ≥28mg/mL | [form ]
solid | [pka]
13.94±0.70(Predicted) | [color ]
Off-white | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| Hazard Information | Back Directory | [Description]
JNJ-1661010 (681136-29-8) is a potent and selective FAAH inhibitor. Initially forms a covalent adduct with FAAH but is slowly released, IC50 = 12 nM. 100-fold selectivity for FAAH-1 over FAAH-2. Cell permeable and active in vivo. JNJ-1661010 displays analgesic activity in various animal models. | [Uses]
JNJ-1661010, is used to examine the contribution of endocannabinoid signaling in experimental fibrosis. In biological studies, this compound had shown to elevate the levels of arachidonoyl ethanolamide (AEA) in rat brains. | [Definition]
ChEBI: JNJ-1661010 is a N-arylpiperazine. | [Biological Activity]
Selective, reversible inhibitor of fatty acid amide hydrolase (FAAH) (IC 50 = 12nM). Brain penetrant and active in vivo . | [Synthesis]
GENERAL STEPS: A solution of 1-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine (1.00 g, 4.06 mmol) and triethylamine (0.565 mL, 4.06 mmol) in tetrahydrofuran (20 mL) was added to a 25 mL round bottom flask. The reaction mixture was cooled to 0°C in an ice bath, followed by slow dropwise addition of phenyl isocyanate (0.529 mL, 4.87 mmol). After the dropwise addition was completed, the ice bath was removed and the reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, diisopropyl ether (40 mL) was added to the mixture to precipitate the product. The solid was collected by filtration and recrystallized with a mixed solvent of hexane and ethyl acetate (1:1, v/v) to afford N-phenyl-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide 1.19 g in 80.4% yield as a white solid. The structure of the product was confirmed by 1H-NMR (CDCl3): δ 3.70 (8H, s), 6.43 (1H, s), 7.06-7.11 (1H, m), 7.29-7.46 (7H, m), 8.17-8.21 (2H, m). | [storage]
Store at +4°C | [References]
1) Karbarz et al. (2009), Biochemical and biological properties of 4-(3-phenyl-[1,2,4]thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a mechanism-based inhibitor of fatty acid amide hydrolase; Anesth. Analg., 108 316 |
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