SML0613
Rofecoxib
≥98% (HPLC)
Synonym(s):
4-[4-(Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone
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About This Item
Empirical Formula (Hill Notation):
C17H14O4S
CAS Number:
Molecular Weight:
314.36
UNSPSC Code:
12352200
NACRES:
NA.77
SMILES string
[S](=O)(=O)(C)c1ccc(cc1)C2=C(C(=O)OC2)c3ccccc3
InChI
1S/C17H14O4S/c1-22(19,20)14-9-7-12(8-10-14)15-11-21-17(18)16(15)13-5-3-2-4-6-13/h2-10H,11H2,1H3
InChI key
RZJQGNCSTQAWON-UHFFFAOYSA-N
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 5 mg/mL, clear (warmed)
storage temp.
2-8°C
Quality Level
Related Categories
Application
Rofecoxib has been used in high performance bioaffinity chromatography.
Biochem/physiol Actions
Rofecoxib is a selective cyclooxygenase-2 (COX-2) inhibitor with >800-fold COX-2 selectivity in CHO cells expressing human COX-1 and COX-2.
Rofecoxib is a selective cyclooxygenase-2 (COX-2) inhibitor.
Rofecoxib is derived from furanone and has the ability to cross human placenta. Along with anti-inflammatory action, it possesses analgesic and antipyretic properties. Cytosolic hepatic enzymes are responsible for the metabolism of rofecoxib. It is known to cause oligohydramnios and ductus arteriosus constrictions. Rofecoxib inhibits the action of CYP1A2 (cytochrome P450 family 1 subfamily A member 2). It might be associated with aseptic meningitis. Rofecoxib is known to ameliorate the risk of colorectal adenoma, but might contribute to toxicity.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Kerstin Rabausch et al.
Circulation research, 96(1), e1-e6 (2004-12-14)
There is concern that cyclooxygenase (COX)-2 inhibitors may promote atherothrombosis by inhibiting vascular formation of prostacyclin (PGI2) and an increased thrombotic risk of COX-2 inhibitors has been reported. It is widely accepted that the prothrombotic effects of COX-2 inhibitors can
Peter Pyrko et al.
Molecular cancer, 5, 19-19 (2006-05-19)
2,5-Dimethyl-celecoxib (DMC) is a close structural analog of the selective cyclooxygenase-2 (COX-2) inhibitor celecoxib (Celebrex) that lacks COX-2-inhibitory function. However, despite its inability to block COX-2 activity, DMC is able to potently mimic the anti-tumor effects of celecoxib in vitro
Krista F Huybrechts et al.
Medical care, 55(6), 545-551 (2017-05-16)
Many countries lack fully functional pharmacovigilance programs, and public budgets allocated to pharmacovigilance in industrialized countries remain low due to resource constraints and competing priorities. Using 3 case examples, we sought to estimate the public health and economic benefits resulting
Rosivaldo S Borges et al.
Molecules (Basel, Switzerland), 24(1) (2019-01-06)
A drug design for safer phenylbutazone was been explored by reactivity and docking studies involving single electron transfer mechanism, as well as toxicological predictions. Several approaches about its structural properties were performed through quantum chemistry calculations at the B3LYP level
Yan-Hui Zou et al.
Frontiers in neuroscience, 14, 817-817 (2020-09-10)
Cyclooxygenase-2 (COX-2) is reported to be activated during the course of amyotrophic lateral sclerosis (ALS) development and progression. However, the roles of COX-2 in aggravating ALS and the underlying mechanism have been largely overlooked. To reveal the mechanisms, the canonical
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