| Identification | Back Directory | [Name]
Imrecoxib | [CAS]
395683-14-4 | [Synonyms]
Imrecoxib
Imrecoxib USP/EP/BP
2H-Pyrrol-2-one, 1,5-dihydro-3-(4-methylphenyl)-4-[4-(methylsulfonyl)phenyl]-1-propyl- | [Molecular Formula]
C21H23NO3S | [MOL File]
395683-14-4.mol | [Molecular Weight]
369.48 |
| Chemical Properties | Back Directory | [Boiling point ]
604.1±55.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: 100 mg/mL (270.65 mM) | [form ]
Solid | [pka]
-2.25±0.60(Predicted) | [color ]
White to off-white | [CAS DataBase Reference]
395683-14-4 |
| Hazard Information | Back Directory | [Clinical Use]
Imrecoxib, a new non-steroid anti-inflammtory drug (NSAID), was launched in China with the trade
name of Hengyang® for the treatment of osteoarthritis in 2012. It was originally designed and
synthesized by Guo and co-workers at the Institute of Materia Medica (IMM) of the Chinese Academy
of Medical Sciences in collaboration with Hengrui Pharmaceuticals. Imrecoxib, which is a moderately
selective COX-2 inhibitor (with IC50 values against COX-1 and COX-2 being 115 ± 28 nM and 18 4
nM, respectively). | [Synthesis]
Imrecoxib has had two synthetic routes reported across several publications. The most likely process-scale route to this drug is described in the scheme, which began with 2-bromo-4'-(methylsulfonyl)-acetophenone (84) and p-tolylacetic acid (85) as starting materials. In the
presence of base, |á-bromoketone 84 was treated with acid 85 which resulted in lactone 86 in 72% yield
across the two-step sequence. Exposure of lactone 86 with propylamine triggered a ring-opening-ring
closing reaction, which resulted in imrecoxib (XIII) directly in 85% yield.
| [storage]
Store at -20°C |
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