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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.
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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
6. Synthesis Route
162011-90-7Total: 18 Synthesis Route
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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