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Key Documents

SML0613

Sigma-Aldrich

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

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

2-8°C

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

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 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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
J Patrick O'Connor et al.
Acta orthopaedica, 80(5), 597-605 (2009-11-18)
Non-steroidal anti-inflammatory drugs (NSAIDs) inhibit cyclooxygenase (COX) activity, which is the rate-limiting enzyme in the synthesis of prostaglandins. Previous studies have indicated that NSAID therapy, and in particular NSAIDs that specifically target the inflammatory cyclooxygenase (COX-2), impair bone healing. We
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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