1291779-76-4

Basic information

• Product Name: BI-99179
• Synonyms: BI-99179;(1R,3S)-N-[4-(1,3-benzoxazol-2-yl)phenyl]-N-methyl-3-(propanoylamino)cyclopentane-1-carboxamide
• CAS NO: 1291779-76-4
• Molecular Formula: C₂₃H₂₅N₃O₃
• Molecular Weight: 391.46
• Mol File: 1291779-76-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BI-99179(CAS DataBase Reference)
• NIST Chemistry Reference: BI-99179(1291779-76-4)
• EPA Substance Registry System: BI-99179(1291779-76-4)

Safety Data

• Hazardous Substances Data: 1291779-76-4(Hazardous Substances Data)

Usage

Biochem/physiol Actions

BI 99179 is a non-cytotoxic (by LDH release; 30 μM, U937) orally available, brain-penetrant, highly potent and selective fatty acid synthase (FAS, FASN) inhibitor (IC50 = 79 nM by cell-free human FAS assay) with little or no inhibitory potency toward a panel of 30 receptors & channels (<20%>10 μM). BI 99179 inhibits cellular FAS activity in vitro (IC50 = 180 nM/human H1975, 600 nM/murine hypothalamic N-42 cells) and increases hypothalamic [malonyl-CoA] in rats in vivo (2 h post 10 mg/kg or 2-24 hr post 100 mg/kg p.o.). Note: adverse effects in rats are reported at day 4 (30 mg/kg) and day 9 (3 mg/kg).

Upstream product

• 71830-08-5 (1R,3S)-3-aminocyclopentanecarboxylic acid 
• 1291779-68-4 (1R,3S)-3-propionylamino-cyclopentanecarboxylic acid 
• 1291779-72-0 (1R,3S)-3-amino-cyclopentanecarboxylic acid N-(4-benzooxazol-2-yl-phenyl)-N-methyl-amide 
• 10541-83-0 N-methyl-p-aminobenzoic acid 
• 95-55-6 2-amino-phenol 
• 1291779-73-1 (1R,3S)-3-amino-cyclopentanecarboxylic acid N-(4-benzooxazol-2-yl-phenyl)-N-methyl-amide trifluoro acetic acid 
• 79-03-8 propionyl chloride 

Relevant articles and documents

Discovery of BI 99179, a potent and selective inhibitor of type i fatty acid synthase with central exposure

Based on a high-throughput screen, cyclopentanecarboxanilides were identified as a new chemotype of non-covalent inhibitors of type I fatty acid synthase (FAS). Starting from initial hits we aimed at generating a tool compound suitable for the in vivo validation of FAS as a therapeutic target. Optimisation yielded BI 99179 which is characterised by high potency, remarkably high selectivity and significant exposure (both peripheral and central) upon oral administration in rats.

CYCLOPENTANECARBOXAMIDE DERIVATIVES, MEDICAMENTS CONTAINING SUCH COMPOUNDS AND THEIR USE

The invention relates to cyclopentanecarboxamide derivatives of formula 1, to their use as Fatty Acid Synthase inhibitors, to methods for their therapeutic use and to pharmaceutical compositions containing them, wherein R1, R2, Rsup