Imrecoxib
- Product Name
- Imrecoxib
- CAS No.
- 395683-14-4
- Chemical Name
- Imrecoxib
- Synonyms
- 2H-Pyrrol-2-one, 1,5-dihydro-3-(4-methylphenyl)-4-[4-(methylsulfonyl)phenyl]-1-propyl-;Imrecoxib;Imrecoxib USP/EP/BP;Imrecoxib (BAP-909);Imrecoxib, 10 mM in DMSO;BAP 909,Cyclooxygenase,Inhibitor,COX,Imrecoxib,inhibit,BAP909;4-(4-(Methylsulfonyl)phenyl)-1-propyl-3-(p-tolyl)-1,5-dihydro-2H-pyrrol-2-one
- CBNumber
- CB03159916
- Molecular Formula
- C21H23NO3S
- Formula Weight
- 369.48
- MOL File
- 395683-14-4.mol
Imrecoxib Property
- 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
- InChI
- InChI=1S/C21H23NO3S/c1-4-13-22-14-19(16-9-11-18(12-10-16)26(3,24)25)20(21(22)23)17-7-5-15(2)6-8-17/h5-12H,4,13-14H2,1-3H3
- InChIKey
- AXMZZGKKZDJGAZ-UHFFFAOYSA-N
- SMILES
- N1(CCC)CC(C2=CC=C(S(C)(=O)=O)C=C2)=C(C2=CC=C(C)C=C2)C1=O
- CAS DataBase Reference
- 395683-14-4
N-Bromosuccinimide Price
- Product number
- CS-0079499
- Product name
- Imrecoxib
- Purity
- 99.38%
- Packaging
- 100mg
- Price
- $80
- Updated
- 2021/12/16
Imrecoxib Chemical Properties,Usage,Production
Uses
Imrecoxib (BAP-909) is a novel and selective cyclooxygenase 2 (COX-2) inhibitor with an IC50 value of 18 nM, it also inhibits COX1- activity with an IC50 value of 115 nM. Imrecoxib (BAP-909) has anti-inflammatory effect[1].
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.
in vivo
Imrecoxib (BAP-909) (gastrointestinal administration; 5-20 mg/kg; 1 hour before carrageenan injection) inhibits carrageenan-induced acute inflammation, and the inhibitory effect is maximal at 4 hours[1]. Imrecoxib (BAP-909) (gastrointestinal administration; 5-20 mg/kg; started on day 7; 26 days) diminishes the secondary paw swelling and inhibits heat-inactivated BCG induced-inflammtory polyarthritis[1].
| Animal Model: | Rat carrageenan-induced edema model[1] |
| Dosage: | 5 mg/kg, 10 mg/kg, 20 mg/kg |
| Administration: | Gastrointestinal administration; 5-20 mg/kg; 1 hour before carrageenan injection |
| Result: | Inhibited the edema response with different doses. |
| Animal Model: | Rat adjuvant-induced arthritis (AIA) model[1] |
| Dosage: | 5 mg/kg, 10 mg/kg, 20 mg/kg |
| Administration: | Gastrointestinal administration; 5-20 mg/kg; started on day 7; 26 days |
| Result: | Inhibited adjuvant-induced chronic inflammation at the doses of 10 and 20 mg/kg. |
IC 50
Human COX-1: 115 nM (IC50); Human COX-2: 18 nM (IC50)
References
[1] Chen XH, et al. Imrecoxib: a novel and selective cyclooxygenase 2 inhibitor with anti-inflammatory effect. Acta Pharmacol Sin. 2004 Jul;25(7):927-31. PMID:15210067
Imrecoxib Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Imrecoxib manufacturers
- Product
- Imrecoxib 395683-14-4
- Price
- US $2.00-5.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2025-07-08
- Product
- Imrecoxib 395683-14-4
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1000kg
- Release date
- 2025-06-12
- Product
- Imrecoxib 395683-14-4
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.9%
- Supply Ability
- 100 Tons Min
- Release date
- 2021-06-16