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Etoricoxib

pharmaceutical raw materials
Etoricoxib structure

Etoricoxib 

structure
  • CAS No:

    202409-33-4

  • Formula:

    C18H15ClN2O2S

  • Chemical Name:

    Etoricoxib

  • 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

  • Categories:

    Active Pharmaceutical Ingredients  >  Antipyretic Analgesics

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

Uses

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.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • METROCHEM API PRIVATE LTD

    United States United States
    Active
  • HETERO LABS LTD

    United States United States
    Active
  • ALEMBIC PHARMACEUTICALS LTD

    United States United States
    Active

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