Valdecoxib

Modify Date: 2024-01-01 20:35:59

Valdecoxib Structure
Valdecoxib structure
 Common Name Valdecoxib
CAS Number 181695-72-7 Molecular Weight 314.359
Density 1.3±0.1 g/cm3 Boiling Point 481.2±55.0 °C at 760 mmHg
Molecular Formula C16H14N2O3S Melting Point 162-164ºC
MSDS Chinese USA Flash Point 244.8±31.5 °C
Symbol GHS08 GHS09
GHS08, GHS09		 Signal Word Warning

 Use of Valdecoxib


Valdecoxib is a highly potent and selective inhibitor of COX-2, with IC50s of 5 nM and 140 μM for COX-2 and COX-1, respeceively. Valdecoxib can be used in the research of arthritis and pain.

 Names

Name valdecoxib
Synonym More Synonyms

 Valdecoxib Biological Activity

Description Valdecoxib is a highly potent and selective inhibitor of COX-2, with IC50s of 5 nM and 140 μM for COX-2 and COX-1, respeceively. Valdecoxib can be used in the research of arthritis and pain.
Related Catalog
Target

COX-2:5 nM (IC50)

COX-1:140 μM (IC50)

In Vitro Valdecoxib (Compound 2) is a highly potent, selective and orally active inhibitor of COX-2, with IC50s of 5 nM and 140 μM for COX-2 and COX-1, respeceively[1]. Valdecoxib (10, 100 µM) inhibits LPS-induced proliferation of endothelial cells and bFGF secretion in a dose-dependent manner. Valdecoxib stimulates VEGF formation via HMEC-1 under inflammatory conditions[2].
In Vivo Valdecoxib (Compound 2) shows potent oral activity in an acute antiinflammatory assay (rat carrageenan foot pad edema; ED50 = 10.2 ± 1.4 mg/kg). Valdecoxib also has chronic antiinflammatory activity in the rat adjuvant arthritis model, with an ED50 of 0.032 ± 0.002 mg/kg/day[1]. Valdecoxib (10 mg/kg, i.p.) significantly attenuates the behavioral and biochemical (oxidative damage) alterations in chronic-stressed mice[3].
Cell Assay HMEC-1 cells proliferation is measured using the MTT conversion method. Cells are seeded (50.000 cells/well) into 96-well plates. The cells are incubated for 24 h with LPS 100 µg/mL, CoCl2 200 µM, Valdecoxib 10 or 100 µM, LPS and Valdecoxib or CoCl2 and Valdecoxib or without tested chemicals (control group). All the substances are added at the same time. After incubation, 50 µL MTT (1 mg/mL) is added and the plates are incubated at 37°C for 4 h. At the end of the experiment, cells are exposed to 100 µL DMSO, which enables the release of the blue reaction product-formazan. The absorbance at 570 nm is read on a microplate reader and results are expressed as a percentage of the absorbance measured in control cells[2].
Animal Admin Mice[3] The drugs including naproxen (14 mg/kg, i.p.), rofecoxib (5 mg/kg, i.p.), meloxicam (5 mg/kg, i.p.), nimesulide (5 mg/kg, i.p.) and Valdecoxib (10 mg/kg, i.p.) are used in the assay. The animals are randomized into 7 groups (n=10 in each group), including the naive group, in which the mice only receive vehicle for 15 d without forced swimming session; the control (chronically stressed) group, in which mice receive vehicle 30 min before the forced swimming session (6 min) for 15 d; the naproxen (14 mg/kg) group; the Valdecoxib (10 mg/kg) group; the rofecoxib (5 mg/kg) group; the meloxicam (5 mg/kg) group; and the nimesulide (5 mg/kg) group. Drugs are suspended in 0.25% carboxymethylcellulose (CMC) and administered intraperitoneally, 30 min before the forced swimming session for 15 consecutive days[3].
References

[1]. Talley JJ, et al. 4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. J Med Chem. 2000 Mar 9;43(5):775-7.

[2]. Wiktorowska-Owczarek A. The effect of valdecoxib on the production of growth factors evoked by hypoxia and bacterial lipopolysaccharide in HMEC-1 cells. Adv Clin Exp Med. 2013 Nov-Dec;22(6):795-800.

[3]. Kumar A, et al. Protective effects of selective and non-selective cyclooxygenase inhibitors in an animal model of chronic stress. Neurosci Bull. 2010 Feb;26(1):17-27.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 481.2±55.0 °C at 760 mmHg
Melting Point 162-164ºC
Molecular Formula C16H14N2O3S
Molecular Weight 314.359
Flash Point 244.8±31.5 °C
Exact Mass 314.072510
PSA 94.57000
LogP 1.71
Vapour Pressure 0.0±1.2 mmHg at 25°C
Index of Refraction 1.609
Storage condition Store at RT

 Safety Information

Symbol GHS08 GHS09
GHS08, GHS09
Signal Word Warning
Hazard Statements H361d-H373-H410
Precautionary Statements P273-P281-P501
Hazard Codes Xn,N
Risk Phrases 63-48/22-51/53
Safety Phrases 36/37-61
RIDADR NONH for all modes of transport
HS Code 2935009090

 Synthetic Route

 Customs

HS Code 2935009090
Summary 2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

 Articles4

More Articles
NFAT2 regulates COX-2 expression and modulates the integrin repertoire in endothelial cells at the crossroads of angiogenesis and inflammation.

Exp. Cell Res. 324(2) , 124-36, (2014)

The mechanisms controlling the switch between the pro-angiogenic and pro-inflammatory states of endothelial cells are still poorly understood. In this paper, we show that: (a) COX-2 expression induced...

Celecoxib increases lung cancer cell lysis by lymphokine-activated killer cells via upregulation of ICAM-1.

Oncotarget 6 , 39342-56, (2015)

The antitumorigenic mechanism of the selective cyclooxygenase-2 (COX-2) inhibitor celecoxib is still a matter of debate. Using lung cancer cell lines (A549, H460) and metastatic cells derived from a l...

Selective determination of COXIBs in environmental water samples by mixed-mode solid phase extraction and liquid chromatography quadrupole time-of-flight mass spectrometry.

J. Chromatogr. A. 1420 , 35-45, (2015)

The development and performance evaluation of a method for the simultaneous determination of six pharmaceuticals belonging to the class of non-steroidal anti-inflammatory drugs (NSAIDs) which present ...

 Synonyms

4-(5-methyl-3-phenylisoxazol-4-yl)benzensulfonamide
Bextra(Valdecoxib)
4-(4-sulfamoylphenyl)-5-methyl-3-phenyl-isoxazole
T5NOJ C1 DR DSZW& ER
4-(5-Methyl-3-phenylisoxazol-4-yl)benzolsulfonamid
Bextra
Valdecoxib
4-[5-methyl-3-phenylisoxazol-4-yl ] benzenesulfonamide
[14C]-Valdecoxib
EINECS 448-010-8
Kudeq
Valdyn
4-(5-Methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide
4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide
p-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide
4-(5-Methyl-3-phenylisoxazol-4-yl)benzenesulfonamide
MFCD00950568
Valdecoxib(R)
Benzenesulfonamide, 4-(5-methyl-3-phenyl-4-isoxazolyl)-
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Related Compounds: More...
Valdecoxib-d3
1219794-90-7
Valdecoxib Dimer
1373038-60-8
Valdecoxib-13C2,15N
1189428-23-6
1-Hydroxy Valdecoxib
181695-81-8
Valdecoxib Sulfonic Acid
181696-35-5
Valdecoxib metabolite M9
501093-54-5
Valdecoxib metabolite M2
501093-49-8
Valdecoxib Sulfonyl Chloride
509074-26-4
Valdecoxib 3'-Sulfonamide Impurity
1373038-56-2
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1158522-08-7
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
940364-43-2
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
134104-43-1
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
131615-57-1
(4-Methyl-tetrahydro-furan-2-yl)-methanol
6906-52-1
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
tert-Butyl-DL-alanine
1375289-11-4
2-[2-Nitro-4-(trifluoromethyl)phenyl]pyrrolidine
1270379-31-1
4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide
849349-65-1
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