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Rofecoxib

Product Name
Rofecoxib
CAS No.
162011-90-7
Chemical Name
Rofecoxib
Synonyms
VIOXX;MK-0966;ROFECOXIB;Rofecoxid;AKOS 92137;Rofecoxib(Vioxx);Rofecoxib (MK0966);Rofecoxib (MK 966);Rofecoxib USP/EP/BP;Rofecoxib 162011-90-7
CBNumber
CB6327130
Molecular Formula
C17H14O4S
Formula Weight
314.36
MOL File
162011-90-7.mol
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Rofecoxib Property

Melting point:
207°C
Boiling point:
577.6±50.0 °C(Predicted)
Density 
1.333±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble5mg/mL, clear (warmed)
form 
powder
color 
white to beige
Water Solubility 
9mg/L(25 ºC)
Merck 
14,8248
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
CAS DataBase Reference
162011-90-7(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
LU5135000
HS Code 
2932.20.3000
Hazardous Substances Data
162011-90-7(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0613
Product name
Rofecoxib
Purity
≥98% (HPLC)
Packaging
10mg
Price
$89.4
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0613
Product name
Rofecoxib
Purity
≥98% (HPLC)
Packaging
50mg
Price
$381
Updated
2024/03/01
TCI Chemical
Product number
R0206
Product name
Rofecoxib
Purity
>98.0%(GC)
Packaging
250mg
Price
$60
Updated
2024/03/01
TCI Chemical
Product number
R0206
Product name
Rofecoxib
Purity
>98.0%(GC)
Packaging
1g
Price
$162
Updated
2024/03/01
Cayman Chemical
Product number
10010260
Product name
Rofecoxib
Purity
≥98%
Packaging
50mg
Price
$86
Updated
2024/03/01
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Rofecoxib Chemical Properties,Usage,Production

Description

Rofecoxib ts a non-steroidal anti-inflammatory drug (NSAID) launched in Mexico, its first market, for the management of acute pain and the treatment of osteoarthritis (OA) and primary dysmenorrhea. Rofecoxib can be obtained by several different ways; one example is by arylation of a 4-bromofuranone with a phenylboronic acid under Suzuki conditions. Rofecoxib is a highly selective inhibitor of COX-2, the inducible isoform of cyclooxygenase and therefore exhibits a potent antiinflammatory activity without concomitant gastric or renal toxicities linked to the non-specific COX-1/2 inhibitors. In several clinical studies in patients with knee or hip osteoarthritis, Rofecoxib was evaluated at 12.5-50 mg doses once daily: it demonstrated efficacy for all primary and secondary endpoints at doses considerably weaker than those for classical non-specific NSAIDs, with good tolerance and less adverse effects. Selective COX-2 inhibitors potentially have a large spectrum of activity including new indications such as Alzheimer's disease, colorectal cancer, irritable bowel disease or urinary incontinence.

Chemical Properties

Off-White (Pale Yellow) Crystalline Powder

Originator

Merck (US)

Uses

A selective cyclooxygenase-2 (COX-2) inhibitor. Use as an anti-inflammatory, analgesic.

Uses

antipsychotic

Uses

Labeled Rizatriptan, intended for use as an internal standard for the quantification of Rizatriptan by GC- or LC-mass spectrometry.

Uses

Rofecoxib has been used in high performance bioaffinity chromatography.

Definition

ChEBI: A butenolide that is furan-2(5H)-one that is substituted by a phenyl group at position 3 and by a p-(methylsulfonyl)phenyl group at position 4. A selective cyclooxygenase 2 inhibitor, it was used from 1999 to 2004 for the tr atment of ostoarthritis, but was withdrawn following concerns about an associated increased risk of heart attack and stroke.

Indications

Rofecoxib is approved for the treatment of osteoarthritis, dysmenorrhea, and acute pain. The most common adverse reactions to rofecoxib are mild to moderate GI irritation (diarrhea, nausea, vomiting, dyspepsia, abdominal pain). Lower extremity edema and hypertension occur relatively frequently (about 3.5%). It is not metabolized by CYP2C9, so rofecoxib should not be subject to some of the interactions seen with celecoxib. However, its metabolism is increased by the coadministration of rifampin, which acts as a nonspecific inducer of hepatic metabolism.

brand name

Vioxx (Merck).

Biochem/physiol Actions

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.

Mechanism of action

Rofecoxib is excreted primarily in the urine (72%) as metabolites. Less than 1% is excreted in the urine as unchanged drug, whereas approximately 14% is excreted in the feces as unchanged drug. Although the metabolism of rofecoxib has not been fully determined, the microsomal cytochrome P450 system appears to play only a minor role—a major difference in the metabolic routes of rofecoxib and celecoxib. The major metabolic route appears to form reduction of the dihydrofuranone ring system by cystolic enzymes to the to cis- and trans- dihydro derivatives. Also isolated is the glucuronide of a hydroxy derivative that results from CYP2C9 oxidative metabolism. None of the isolated metabolites of rofecoxib possess pharmacological activity as COX-1 or COX-2 inhibitors.

Pharmacokinetics

Rofecoxib has been synthesized by a number of synthetic routes that have been summarized elsewhere. It was the second selective COX-2 inhibitor to be marketed. Rofecoxib is well absorbed from the GI tract on oral administration, with peak plasma levels generally being attained within 2 to 3 hours of dosing. Bioavailability averages 93% following administration of a single dose. The area under the plasma concentration–time curve is increased in patients older than 65 years compared to younger adults and is increased slightly in black and Hispanic patients compared with white patients, but the difference is not considered to be clinically significant.

Clinical Use

Rofecoxib was indicated for the relief of the signs and symptoms of osteoarthritis, for the management of acute pain in adults, and for the treatment of primary dysmenorrhea.

Side effects

Rofecoxib causes a significantly lower incidence of upper-gastrointestinal adverse effects (perforations, ulcers, and bleeding) than conventional NSAIDs. Most common adverse events associated with rofecoxib are diarrhoea, headache, nausea, and upper respiratory tract infection.

Synthesis

Rofecoxib can be obtained by different synthetic routes, e.g., by condensation of phenylacetic acid with ethyl bromoacetate to ethyl 2-phenylacetoxyacetate, which is then cyclized to a hydroxyfuranone. Subsequently, the hydroxyfuranone reacts with trifluoromethanesulfonic (triflic) anhydride to the corresponding triflate which reacts with LiBr to yield a bromofuranone. The bromofuranone is condensed with 4- (methylsulfanyl)phenylboronic acid to give 4-[4-(methylsulfanyl)phenyl]-3-phenylfuran- 2(5H)-one which is finally oxidized to rofecoxib.

IC 50

IC50 for COX-2: 1.8 × 10?8 M
IC50 for COX-1: 1.5 × 10?5 M

Dosage

Rofecoxib is indicated for relief of the signs and symptoms of osteoarthritis (recommended starting dose is 12.5 mg once daily, maximum recommended dose is 25 mg/d), for the management of acute pain in adults and for the treatment of primary dysmenorrhea (recommended initial doses are 50 mg once daily, use of rofecoxib for more than 5 d in management of pain has not been studied).

References

1) Chan et al. (1999), Rofecoxib [Vioxx, MK-0966; 4-(4′-methylsulfonylphenyl)-3-phenyl-2-(5H)-furanone]: a potent and orally active cyclooxygenase-2 inhibitor. Pharmacological and biochemical profiles; J. Pharmacol. Exp. Ther., 290 551 2) Catalla-Lawson et al. (2013), Effects of specific inhibition of cyclooxygenase-2 on sodium balance, hemodynamics and vasoactive eicosanoids; J. Pharmacol. Exp. Ther., 289 735

Rofecoxib Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Rofecoxib manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Rofecoxib 162011-90-7
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-04-29
Shaanxi Dideu Medichem Co. Ltd
Product
Rofecoxib 162011-90-7
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-05-07
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Rofecoxib 162011-90-7
Price
US $0.00/G
Min. Order
1G
Purity
98%min
Supply Ability
300KG/month
Release date
2023-01-10

162011-90-7, RofecoxibRelated Search:


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  • 4-[4-(Methylsulfonyl)phenyl]-3-phenyl-
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  • Rofecoxib (MK0966)
  • Rofecoxid
  • ROFECOXIB
  • MK-0966
  • VIOXX
  • AKOS 92137
  • 4-[4-(METHYLSULFONYL)-PHENYL]-3-PHENYL-2(5H)-FURANONE
  • 4-[4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5h)-one
  • Rofecoxib, MK-0966, 4-[4-(methylsulfonyl)-phenyl]-3-phenyl-2(5H)-furanone
  • 2(5H)-Furanone, 4-4-(methylsulfonyl)phenyl-3-phenyl-
  • Rofecoxib USP/EP/BP
  • 4-(4-methanesulfonylphenyl)-3-phenyl-2,5-dihydrofuran-2-one
  • Rofecoxib (MK 966)
  • RofecoxibQ: What is Rofecoxib Q: What is the CAS Number of Rofecoxib Q: What is the storage condition of Rofecoxib Q: What are the applications of Rofecoxib
  • Rofecoxib 162011-90-7
  • 162011-90-7
  • 1984-11-7
  • C17H14O4S
  • C15H13N5D6C7H6O2
  • TRILEPTAL
  • Active Pharmaceutical Ingredients
  • Aromatics
  • Heterocycles
  • Sulfur & Selenium Compounds
  • Osteoarthritis and Rheumatoid Arthritis
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals