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Rofecoxib

Rofecoxib
Rofecoxib structure
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;4-[4-(Methylsulfonyl)phenyl]-3-phenyl-
CBNumber:
CB6327130
Molecular Formula:
C17H14O4S
Formula Weight:
314.36
MOL File:
162011-90-7.mol

Rofecoxib Properties

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
CAS DataBase Reference
162011-90-7(CAS DataBase Reference)
FDA UNII
0QTW8Z7MCR
NCI Dictionary of Cancer Terms
rofecoxib; Vioxx
NCI Drug Dictionary
rofecoxib
ATC code
M01AH02
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Hazard Codes  Xn
Risk Statements  22
WGK Germany  3
RTECS  LU5135000

Rofecoxib price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0613 Rofecoxib ≥98% (HPLC) 162011-90-7 10mg $74.9 2021-12-16 Buy
Sigma-Aldrich SML0613 Rofecoxib ≥98% (HPLC) 162011-90-7 50mg $319 2021-12-16 Buy
TCI Chemical R0206 Rofecoxib >98.0%(GC) 162011-90-7 250mg $45 2021-12-16 Buy
TCI Chemical R0206 Rofecoxib >98.0%(GC) 162011-90-7 1g $122 2021-12-16 Buy
Cayman Chemical 10010260 Rofecoxib ≥98% 162011-90-7 50mg $69 2021-12-16 Buy

Rofecoxib Chemical Properties,Uses,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.

Rofecoxib synthesis

103-82-2
50413-24-6
162011-90-7
Synthesis of Rofecoxib from Phenylacetic acid and 2-Bromo-1-[4-(methylsulfonyl)phenyl]-1-ethanone

Rofecoxib Preparation Products And Raw materials

Raw materials

Preparation Products


Rofecoxib Suppliers

Global( 241)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86(0)13336195806 +86-571-85586718
+86-571-85864795 sales@capotchem.com China 20012 60
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 497 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26782 60
career henan chemical co
+86-0371-55982848
sales@coreychem.com China 29953 58
Shandong chuangyingchemical Co., Ltd.
18853181302
sale@chuangyingchem.com CHINA 5917 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 37282 58
Alchem Pharmtech,Inc.
8485655694
sales@alchempharmtech.com United States 63726 58
Shenzhen Excellent Biotech Co., Ltd.
13480692018
ramyan@ex-biotech.com;sale@ex-biotech.com CHINA 955 58
HENAN BON INDUSTRIAL CO.,LTD
0371-55170695
info@hnbon.com CHINA 26742 58
Shaanxi Dideu Medichem Co. Ltd
13772537765
029-88380327 1010@dideu.com CHINA 3993 58

View Lastest Price from Rofecoxib manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-07-20 Rofecoxib
162011-90-7
US $1.00-1.00 / KG 1g 99% 50tons Shaanxi Dideu Medichem Co. Ltd
2021-07-20 Rofecoxib
162011-90-7
US $1.00-1.00 / KG 1g 99% 50tons Shaanxi Dideu Medichem Co. Ltd
2021-07-02 rofecoxib
162011-90-7
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd

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