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Rofecoxib structure
Rofecoxib structure

Rofecoxib

Iupac Name:3-(4-methylsulfonylphenyl)-4-phenyl-2H-furan-5-one
CAS No.:162011-90-7
Molecular Weight:314.35566
Introduction: Rofecoxib ts a non-steroidal anti-inflammatory drug (NSAID) launchedin Mexico, its first market, for the management of acute pain and the treatmentof osteoarthritis (OA) and primary dysmenorrhea. Rofecoxib can be obtained byseveral different ways; one example is by arylation of a 4-bromofuranone with aphenylboronic acid under Suzuki conditions. Rofecoxib is a highly selectiveinhibitor of COX-2, the inducible isoform of cyclooxygenase and thereforeexhibits a potent antiinflammatory activity without concomitant gastric or renaltoxicities linked to the non-specific COX-1/2 inhibitors. In several clinical studiesin patients with knee or hip osteoarthritis, Rofecoxib was evaluated at 12.5-50mg doses once daily: it demonstrated efficacy for all primary and secondary endpoints at doses considerably weaker than those for classical non-specificNSAIDs, with good tolerance and less adverse effects. Selective COX-2inhibitors potentially have a large spectrum of activity including new indicationssuch as Alzheimer's disease, colorectal cancer, irritable bowel disease orurinary incontinence. View more+
1. Names and Identifiers
1.1 Name
Rofecoxib
1.2 Synonyms

2(5H)-Furanone, 4-[4-(methylsulfonyl)phenyl]-3-phenyl- 2(5H)-Furanone,4-[4-(methylsulfonyl)phenyl]-3-phenyl- 3-(4-Methanesulfonylphenyl)-2-phenyl-2-buten-4-olide 3-Phenyl-4-[4-(Methylsulfonyl)phenyl]-2(5H)-furanone 4-(4-(Methanesulfonyl)phenyl)-3-phenyl-5H-furan-2-one 4-[(4-Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone 4-[4-(Methanesulfonyl)phenyl]-3-phenyl-5H-furan-2-one 4-[4-(MethylSLdfonyl)phenyl]-3-phenyl-2(5H)-furanone 4-[4-(Methylsulfonyl)phenyl]-3-phenyl- 4-[4-(Methylsulfonyl)phenyl]-3-phenyl-2(5H)-furanone Ceeoxx Ceoxx MK 0966 MK 966 MK-0966 Rhuma-cure ROFECOXIB Rofecoxib (MK0966) Rofecoxib(Vioxx) Rofecoxid Romacox VIOXX

1.3 CAS No.
162011-90-7
1.4 CID
5090
1.5 EINECS(EC#)
1806241-263-5
1.6 Molecular Formula
C17H14O4S (isomer)
1.7 Inchi
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
1.8 InChkey
RZJQGNCSTQAWON-UHFFFAOYSA-N
1.9 Canonical Smiles
CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
1.10 Isomers Smiles
CS(=O)(=O)C1=CC=C(C=C1)C2=C(C(=O)OC2)C3=CC=CC=C3
2. Properties
3.1 Density
1.333
3.1 Melting point
207℃
3.1 Boiling point
577.6 °C at 760 mmHg
3.1 Refractive index
1.619
3.1 Flash Point
303.1 °C
3.1 Vapour pressure
2.42E-13mmHg at 25°C
3.1 Precise Quality
314.06100
3.1 PSA
68.82000
3.1 logP
3.63850
3.1 Solubility
DMSO: soluble5mg/mL, clear (warmed)
3.2 Appearance
off-white (pale yellow) crystalline powder
3.3 Chemical Properties
Off-White (Pale Yellow) Crystalline Powder
3.4 Color/Form
White to off-white to light yellow powder
3.5 Water Solubility
Sparingly soluble in acetone, slightly soluble in methanol and isopropyl acetate, very slightly soluble in ethanol, practically insoluble in octanol, and insoluble in water.
In water, 472 mg/L at 25 deg C /Estimated/
3.6 StorageTemp
Refrigerator
3. Use and Manufacturing
4.1 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 tratment of ostoarthritis, but was withdrawn following concerns about an associated increased risk of heart attack and stroke.
4.2 Usage
A selective cyclooxygenase-2 (COX-2) inhibitor. Use as an anti-inflammatory, analgesic.
4. Safety and Handling
5.1 Hazard Codes
Xn
5.1 Risk Statements
22
5.1 Octanol/Water Partition Coefficient
log Kow = 1.56 /Estimated/
5.2 DisposalMethods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
5.3 Formulations/Preparations
Vioxx
Oral: Tablets: 12.5 mg Vioxx (Merck); 25 mg Vioxx (Merck); 50 mg Vioxx (Merck). Oral Suspension: 12.5 mg/5 mL Vioxx (Merck); 25 mg/5 mL Vioxx (Merck).
5.4 WGK Germany
2
5.4 RTECS
LU5135000
5.4 Specification

?Rofecoxib (CAS NO.162011-90-7) is also named as 3-Phenyl-4-(4-(methylsulfonyl)phenyl))-2(5H)-furanone ; 4-(4-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone ; 4-(p-(Methylsulfonyl)phenyl)-3-phenyl-2(5H)-furanone ; CCRIS 8967 ; Ceoxx ; HSDB 7262 ; MK 0966 ; MK 966 ; MK0966 ; UNII-0QTW8Z7MCR ; Vioxx .?Rofecoxib (CAS NO.162011-90-7) is off-white?to pale yellow crystalline powder.

5.5 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 20mg/kg/4W-I (20mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Annals of Internal Medicine. Vol. 133, Pg. 394, 2000.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Merck
14,8248
8.1 Chemical Properties
Off-White (Pale Yellow) Crystalline Powder
8.2 Uses
A selective cyclooxygenase-2 (COX-2) inhibitor. Use as an anti-inflammatory, analgesic.
8.3 Uses
antipsychotic
8.4 Uses
Labeled Rizatriptan, intended for use as an internal standard for the quantification of Rizatriptan by GC- or LC-mass spectrometry.
8.5 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.
8.6 Brand name
Vioxx (Merck).
9. Computational chemical data
  • Molecular Weight:314.35566g/mol
  • Molecular Formula:C17H14O4S
  • Compound Is Canonicalized:True
  • XLogP3-AA:2.3
  • Exact Mass:314.06128010
  • Monoisotopic Mass:314.06128010
  • Complexity:556
  • Rotatable Bond Count:3
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:4
  • Topological Polar Surface Area:68.8
  • Heavy Atom Count:22
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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