Parecoxib
Parecoxib Basic information
- Product Name:
- Parecoxib
- Synonyms:
-
- Parecoxib (free)
- N-[4-(5-methyl-3-phenyl-oxazol-4-yl)phenyl]sulfonylpropanamide
- N-((4-(5-Methyl-3-phenyl-2,3-dihydrooxazol-4-yl)phenyl)sulfonyl)propionaMide
- N-(4-(5-Methyl-3-phenylisoxazol-4-yl)phenylsulfonyl)propionaMide
- Parecoxib SodiuM IMpurity W
- Valdecoxib Impurity J
- SC 69124
- Valus-P
- CAS:
- 198470-84-7
- MF:
- C19H18N2O4S
- MW:
- 370.42
- EINECS:
- 803-261-6
- Product Categories:
-
- Inhibitors
- ZY
- Mol File:
- 198470-84-7.mol
Parecoxib Chemical Properties
- Melting point:
- 148.9-151°
- Density
- 1.264
- storage temp.
- 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 5.08±0.10(Predicted)
- color
- White to off-white
- BRN
- 8640266
- InChI
- InChI=1S/C19H18N2O4S/c1-3-17(22)21-26(23,24)16-11-9-14(10-12-16)18-13(2)25-20-19(18)15-7-5-4-6-8-15/h4-12H,3H2,1-2H3,(H,21,22)
- InChIKey
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N
- SMILES
- C(NS(C1=CC=C(C2=C(C)ON=C2C2=CC=CC=C2)C=C1)(=O)=O)(=O)CC
Safety Information
- Hazard Codes
- Xn,N
- Risk Statements
- 63-48/22-51/53
- Safety Statements
- 36/37-61
- WGK Germany
- 3
- RTECS
- TX1478700
Parecoxib Usage And Synthesis
Uses
Anti-inflammatory; analgesic (cyclooxygenase COX-2 inhibitor).
Uses
Parecoxib is used in the combination with Telmisartan for the treatment of endometriosis. Parecoxib reduces hippocampal inflammation and improve short-term memory function through the inhibition of COX-2 expression in aged rats after splenectomy.
Definition
ChEBI: An N-acylsulfonamide resulting from the formal condensation of valdecoxib with propionic acid. It is a prodrug for valdecoxib.
Synthesis
123-62-6
181695-72-7
198470-84-7
General procedure for the synthesis of N-((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)propionamide from propionic anhydride and 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide: 3.1 grams (10 mmol) of 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide was mixed with 3.5 grams (35 mmol) of triethylamine and 2.6 g (20 mmol) propionic anhydride in 20 mL of chloromethane. After completion of the reaction, the reaction mixture was poured into water and extracted with dichloromethane. The extract was concentrated, dissolved in ethanol, crystallized 5 to 10 times, filtered and dried to give 3.4 g of N-((4-(5-methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)propionamide in 92.5% yield and 99.77% purity.
in vivo
Parecoxib (intraperitoneal injection; 2.5, 5.0 or 10?mg/kg; once a day; 21?days) does not affect locomotor activity in the elevated plus-maze test, and Parecoxib at 5 and 10?mg/kg shows higher levels of percentage of time spent in the open arms[3].
| Animal Model: | Naive adult male ICR mice, 15?weeks old and weighing 25-35?g[3] |
| Dosage: | 2.5, 5.0 or 10?mg/kg |
| Administration: | Intraperitoneal injection; 2.5, 5.0 or 10?mg/kg; once a day; 21?days |
| Result: | Exerted an anxiolytic-like effect in the elevated plus-maze test |
IC 50
COX-2
References
[1] Patent: CN105859647, 2016, A. Location in patent: Paragraph 0048; 0049; 0050
[2] Patent: CN106008387, 2016, A. Location in patent: Paragraph 0020; 0048; 0049; 0050
[3] Patent: CN106008386, 2016, A. Location in patent: Paragraph 0021; 0056; 0057; 0058
[4] Journal of Medicinal Chemistry, 2000, vol. 43, # 9, p. 1661 - 1663
[5] Patent: CN106674142, 2017, A. Location in patent: Paragraph 0038-0048
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