Etoricoxib
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Etoricoxib
structure -
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CAS No:
202409-33-4
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Formula:
C18H15ClN2O2S
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Chemical Name:
Etoricoxib
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Synonyms:
2,3′-Bipyridine,5-chloro-6′-methyl-3-[4-(methylsulfonyl)phenyl]-;5-Chloro-6′-methyl-3-[4-(methylsulfonyl)phenyl]-2,3′-bipyridine;Etoricoxib;MK 663;MK 0663;Arcoxia;Torcoxia;Kingcox;Etocox;Etobrix;Etoxib;Etropain;Algix;Tauxib;Nucoxia;Etosaid
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CAS No:
Description
Etoricoxib is a non steroidal anti-inflammatory agent, acting as a selective and orally active COX-2 inhibitor, with IC50s of 1.1 μM and 116 μM for COX-2 and COX-1 in human whole blood.
Solid
Etoricoxib is a member of the class of bipyridines that is 2,3'-bipyridine which is substituted at the 3, 5, and 6' positions by 4-(methylsulfonyl)phenyl, chlorine, and methyl groups, respectively. It has a role as a cyclooxygenase 2 inhibitor and a non-steroidal anti-inflammatory drug. It is a sulfone, a member of bipyridines and an organochlorine compound.|Etoricoxib is a new COX-2 selective inhibitor. Current therapeutic indications are: treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout. Like any other COX-2 selective inhibitor, Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme (COX-2) to reduce the generation of prostaglandins (PGs) from arachidonic acid. It is approved in more than 60 countries worldwide but not in the US.|Etoricoxib is a synthetic, nonsteroidal anti-inflammatory drug (NSAID) with antipyretic, analgesic, and potential antineoplastic properties. Etoricoxib specifically binds to and inhibits the enzyme cyclooxygenase-2 (COX-2), resulting in inhibition of the conversion of arachidonic acid into prostaglandins. Inhibition of COX-2 may induce apoptosis and inhibit tumor cell proliferation and angiogenesis.|A sulfone and pyridine derivative that acts as a cyclooxygenase-2 inhibitor. It is used as a NSAID for the treatment of pain associated with RHEUMATOID ARTHRITIS and ANKYLOSING SPONDYLITIS. It is also used for the short-term treatment of moderate postoperative dental pain.
Etoricoxib Basic Attributes
358.84
358.84
1592732-453-0
WRX4NFY03R
DTXSID3046457
C52188
M01AH05|M - Musculo-skeletal system
2933399090
Characteristics
68.3
3.3
Solid
1.3±0.1 g/cm3
134-135°C
510°C at 760 mmHg
262.2±30.1 °C
1.601
3.28e-03 g/L
-20°C Freezer
5.17E-10mmHg at 25°C
Safety Information
UN 2811 6.1 / PGII
3
22-24
36/37-45
T
P280-P302 + P350-P310
H302-H310
|Danger|H302 (98.78%): Harmful if swallowed [Warning Acute toxicity, oral]|P260, P262, P264, P270, P273, P280, P301+P312, P302+P350, P310, P314, P322, P330, P361, P363, P405, and P501|Aggregated GHS information provided by 82 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
This reduced activity is the cause of reduced gastrointestinal toxicity, as demonstrated in several large clinical trials performed with different COXIB (see below links on NEJM and The Lancet). Some clinical trials and meta-analysis showed that treatment with COXIB lead to increased incidence of cardiovascular adverse events compared to placebo
92%
Drug Information
For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout.
Etoricoxib is a COX-2 selective inhibitor (approximately 106 times more selective for COX-2 inhibition over COX-1).
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)|A subclass of cyclooxygenase inhibitors with specificity for CYCLOOXYGENASE-2. (See all compounds classified as Cyclooxygenase 2 Inhibitors.)
Bioavailability is 100% following oral administration.
Hepatic, primarily via CYP3A4.|Etoricoxib has known human metabolites that include 6-Hydroxymethyletoricoxib and Etoricoxib 1'-N'-oxide.
22 hours
Like any other COX-2 selective inhibitor Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme (COX-2), preventing production of prostaglandins (PGs) from arachidonic acid.
Arcoxia
Etoricoxib Use and Manufacturing
Etoricoxib is a dipyridinyl compound that demonstrates high in vitro and ex vivo selectivity for COX-2 over COX-1 in several assays, e.g., in the production of PGE2 by CHO cells expressing either COX-2 (IC50 = 79 nM) or COX-1 (IC50 > 50 μM). Oral etoricoxib is well absorbed and metabolized extensively via oxidation, with metabolites excreted largely in the urine.[Cayman Chemical]
Pharmaceuticals
Computed Properties
Molecular Weight:358.8
XLogP3:3.3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:358.0542766
Monoisotopic Mass:358.0542766
Topological Polar Surface Area:68.3
Heavy Atom Count:24
Complexity:514
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
It is a nonsteroidal anti-inflammatory drug with anti-inflammatory, analgesic and antipyretic effects in animal models. It is a selective cyclooxygenase-2 (COX-2) inhibitor that can relieve symptoms and signs such as pain, inflammation and fever, reduce gastrointestinal side effects and does not affect platelet function.
Registered Holders
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METROCHEM API PRIVATE LTD
Active
United States
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HETERO LABS LTD
Active
United States
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ALEMBIC PHARMACEUTICALS LTD
Active
United States
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