MM-433593

• CAT Number: I008119
• CAS Number: 1006604-91-6
• Molecular Formula: C25H22ClN3O3
• Molecular Weight: 447.919
• Purity: ≥95%
• Synonyms: MM-433593; MM-433593; MM-433593;2-(1-(4-chlorobenzyl)-2,5-dimethyl-1H-indol-3-yl)-N-(2-methoxypyridin-4-yl)-2-oxoacetamide
• Target: Fatty Acid Amide Hydrolase (FAAH) Inhibitor
• Solubility: Soluble in DMSO
• Storage: Desiccate at RT
• IUPAC Name: 2-[1-[(4-chlorophenyl)methyl]-2,5-dimethylindol-3-yl]-N-(2-methoxypyridin-4-yl)-2-oxoacetamide
• InChI: InChI=1S/C25H22ClN3O3/c1-15-4-9-21-20(12-15)23(16(2)29(21)14-17-5-7-18(26)8-6-17)24(30)25(31)28-19-10-11-27-22(13-19)32-3/h4-13H,14H2,1-3H3,(H,27,28,31)
• InChIKey: RIKZRSJVZWKHNX-UHFFFAOYSA-N
• SMILES: CC1=CC2=C(C=C1)N(C(=C2C(=O)C(=O)NC3=CC(=NC=C3)OC)C)CC4=CC=C(C=C4)Cl

MM-433593 a fatty acid amide hydrolase (FAAH) inhibitor potentially for the treatment of pain, inflammation, and other disorders.

Reference

1:Pharmacol Res Perspect. 2014 Oct;2(5):e00059. doi: 10.1002/prp2.59. Epub 2014 Jul 2. Metabolism and disposition of MM-433593, a selective FAAH-1 inhibitor, in monkeys.Banijamali AR,Wakefield JD,Mermerian AH,Busby RW, PMID: 25505606 PMCID: PMC4186420 DOI: 10.1002/prp2.59 Abstract: MM-433593 is a highly potent and selective inhibitor of fatty acid amide hydrolase-1 (FAAH-1) with potential utility as an orally administered treatment of pain, inflammation, and other disorders. In this study, we investigated the metabolism and pharmacokinetics of MM-433593 in monkeys, and compared plasma and urine metabolites of this compound to the in vitro metabolites produced by monkey hepatocytes. Intravenous administration of MM-433593 to cynomolgus monkeys produced a rapid distribution phase and slower elimination phase with a mean systemic clearance rate of 8-11 mL/min/kg. Absolute oral bioavailability was determined to be 14-21% with maximum plasma concentrations reached ∼3 h (T max) following a 10 mg/kg oral dose. The average terminal half-life of MM-433593 was 17-20 h, and there were no qualitative sex differences in the metabolite profile of MM-433593. The major site of metabolism was oxidation of the methyl group at the five position of the indole ring, which was confirmed by chromatography and mass spectrometry comparison to a synthesized authentic standard. This metabolite was further oxidized to the corresponding carboxylic acid and/or conjugated with sulfate, glucuronide, or glutathione. In all, 18 metabolites were found in plasma and urine. In vitro incubations of MM-433593 with monkey hepatocytes yielded 13 metabolites, all of which were found in vivo, indicating a good correlation between the in vitro and in vivo metabolism data. A comprehensive pathway for the metabolism of MM-433593 is proposed, including a plausible, five-step biotransformation for the formation of N-acetylcysteine conjugate metabolite (M18) from the hydroxylated parent (M5).