Etoricoxib | CAS#202409-33-4 | anti-inflammatory

Etoricoxib
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317858

CAS#: 202409-33-4

Description: 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.

Chemical Structure

Etoricoxib

CAS# 202409-33-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317858
Name: Etoricoxib
CAS#: 202409-33-4
Chemical Formula: C18H15ClN2O2S
Exact Mass: 358.05
Molecular Weight: 358.842
Elemental Analysis: C, 60.25; H, 4.21; Cl, 9.88; N, 7.81; O, 8.92; S, 8.94

Price and Availability

Size	Price	Availability
100mg	USD 400	2 Weeks
250mg	USD 750	2 weeks
500mg	USD 1350	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 202409-40-3 (HCl)

Synonym: Etoricoxib, Arcoxia, L-791456, MK 0663, MK-0663

IUPAC/Chemical Name: 5-Chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine

InChi Key: MNJVRJDLRVPLFE-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3

SMILES Code: O=S(C1=CC=C(C2=CC(Cl)=CN=C2C3=CC=C(C)N=C3)C=C1)(C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Etoricoxib (MK-0663) 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.
In vitro activity:	Prostaglandin E2 (PG-E2) secretion (ELISA, Figure 2(a)) was significantly regulated both by the mechanical strain applied to the hPDL cells and by etoricoxib (F = 55.08; df1/2 = 5/13.56, p < 0.001). Force application significantly increased PG-E2 synthesis in the control group (p = 0.024), whereas etoricoxib at cell medium concentrations of 3.29 μM and 5.49 μM significantly inhibited PG-E2 synthesis in both the presence (p = 0.002) and absence (p < 0.001) of mechanical compressive strain compared to the respective 0 μM controls. Reference: Mediators Inflamm. 2019; 2019: 2514956. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6431464/
In vivo activity:	HCC was induced by DENA (150 mg/kg/week; i.p) for 2 weeks, then 2AAF (20 mg/kg; p.o) every other day for three successive weeks. Etoricoxib (0.6 mg/kg, p.o.) was given to DENA/2AAF-administered rats for 20 weeks. Etoricoxib significantly suppressed alpha-fetoprotein (AFP) and carbohydrate antigen 19-9 (CA19.9) as liver tumor biomarkers. It also decreased serum aspartate aminotransferase (AST), alanine aminotransferase (ALT), and total bilirubin levels while increasing serum albumin levels. Besides, it alleviated DENA/2AAF-induced histopathological abrasions and inflammatory cell infiltration. Furthermore, etoricoxib showed a potent antioxidant effect, supported by a significant lipid peroxide reduction and elevation in superoxide dismutase and GSH content activity. In addition, Etoricoxib significantly down-regulated the protein expression of interleukin 1 beta (IL-1β), tumor necrosis factor α (TNFα), nuclear Factor-kappa B (NF-κB), phosphorylated nuclear Factor-kappa B (p-NF-κB), cyclooxygenase-2 (COX-2), and prostaglandin E2 (PGE2). Reference: Curr Mol Pharmacol. 2021 Jul 7. https://pubmed.ncbi.nlm.nih.gov/34238176/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	85.5	238.27
	Ethanol	46.0	128.19

Preparing Stock Solutions

The following data is based on the product molecular weight 358.84 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Kirschneck C, Küchler EC, Wolf M, Spanier G, Proff P, Schröder A. Effects of the Highly COX-2-Selective Analgesic NSAID Etoricoxib on Human Periodontal Ligament Fibroblasts during Compressive Orthodontic Mechanical Strain. Mediators Inflamm. 2019 Mar 10;2019:2514956. doi: 10.1155/2019/2514956. PMID: 30983880; PMCID: PMC6431464. 2. Honjo H, Uwai Y, Iwamoto K. Inhibitory effect of selective cyclooxygenase-2 inhibitor etoricoxib on human organic anion transporter 3 (hOAT3). Drug Metab Lett. 2011 Apr;5(2):140-37. doi: 10.2174/187231211795305285. PMID: 21457143. 3. Ali GF, Omar HA, Hersi F, Abo-Youssef AM, Ahmed OM, Mohamed WR. The protective role of etoricoxib against diethylnitrosamine/2-acetylaminofluorene-induced hepatocarcinogenesis in Wistar rats: The impact of NF-κB/COX-2/PGE2 signaling. Curr Mol Pharmacol. 2021 Jul 7. doi: 10.2174/1874467214666210708103752. Epub ahead of print. PMID: 34238176. 4. Oberberg S, Nottenkämper J, Heukamp M, Krapp J, Willburger RE. Etoricoxib is safe and effective in preventing heterotopic ossification after primary total hip arthroplasty. J Orthop Surg Res. 2021 Feb 27;16(1):163. doi: 10.1186/s13018-021-02297-6. PMID: 33639986; PMCID: PMC7912510.
In vitro protocol:	1. Kirschneck C, Küchler EC, Wolf M, Spanier G, Proff P, Schröder A. Effects of the Highly COX-2-Selective Analgesic NSAID Etoricoxib on Human Periodontal Ligament Fibroblasts during Compressive Orthodontic Mechanical Strain. Mediators Inflamm. 2019 Mar 10;2019:2514956. doi: 10.1155/2019/2514956. PMID: 30983880; PMCID: PMC6431464. 2. Honjo H, Uwai Y, Iwamoto K. Inhibitory effect of selective cyclooxygenase-2 inhibitor etoricoxib on human organic anion transporter 3 (hOAT3). Drug Metab Lett. 2011 Apr;5(2):140-37. doi: 10.2174/187231211795305285. PMID: 21457143.
In vivo protocol:	1. Ali GF, Omar HA, Hersi F, Abo-Youssef AM, Ahmed OM, Mohamed WR. The protective role of etoricoxib against diethylnitrosamine/2-acetylaminofluorene-induced hepatocarcinogenesis in Wistar rats: The impact of NF-κB/COX-2/PGE2 signaling. Curr Mol Pharmacol. 2021 Jul 7. doi: 10.2174/1874467214666210708103752. Epub ahead of print. PMID: 34238176. 2. Oberberg S, Nottenkämper J, Heukamp M, Krapp J, Willburger RE. Etoricoxib is safe and effective in preventing heterotopic ossification after primary total hip arthroplasty. J Orthop Surg Res. 2021 Feb 27;16(1):163. doi: 10.1186/s13018-021-02297-6. PMID: 33639986; PMCID: PMC7912510.

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1: Cochrane DJ, Jarvis B, Keating GM. Etoricoxib. Drugs. 2002;62(18):2637-51; discussion 2652-3. doi: 10.2165/00003495-200262180-00006. PMID: 12466002.

2: la Torre LF, Franco-González DL, Brennan-Bourdon LM, Molina-Frechero N, Alonso-Castro ÁJ, Isiordia-Espinoza MA. Analgesic Efficacy of Etoricoxib following Third Molar Surgery: A Meta-analysis. Behav Neurol. 2021 Sep 8;2021:9536054. doi: 10.1155/2021/9536054. PMID: 34539935; PMCID: PMC8445708.

3: Matsumoto AK, Cavanaugh PF Jr. Etoricoxib. Drugs Today (Barc). 2004 May;40(5):395-414. PMID: 15319795.

4: Zhang S, Zhang Y, Liu P, Zhang W, Ma JL, Wang J. Efficacy and safety of etoricoxib compared with NSAIDs in acute gout: a systematic review and a meta- analysis. Clin Rheumatol. 2016 Jan;35(1):151-8. doi: 10.1007/s10067-015-2991-1. Epub 2015 Jun 24. PMID: 26099603.

5: Leclercq P, Malaise MG. Le médicament du mois. Etoricoxib (Arcoxia) [Etoricoxib (Arcoxia)]. Rev Med Liege. 2004 May;59(5):345-9. French. PMID: 15270001.

6: Marek CL, Hellstein JW. MORE ON ETORICOXIB. J Am Dent Assoc. 2019 Sep;150(9):735-736. doi: 10.1016/j.adaj.2019.07.015. PMID: 31439199.

7: Wenckus CS. UNCOMMON ETORICOXIB. J Am Dent Assoc. 2019 Sep;150(9):735. doi: 10.1016/j.adaj.2019.07.014. PMID: 31439200.

8: Lories RJ. Etoricoxib and the treatment of ankylosing spondylitis. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1599-608. doi: 10.1517/17425255.2012.741120. Epub 2012 Nov 6. PMID: 23126318.

9: Martínez Antón MD, Galán Gimeno C, Sánchez de Vicente J, Jáuregui Presa I, Gamboa Setién PM. Etoricoxib-induced fixed drug eruption: Report of seven cases. Contact Dermatitis. 2021 Mar;84(3):192-195. doi: 10.1111/cod.13659. Epub 2020 Aug 18. PMID: 32666601.

10: Schmidt M, Sørensen HT, Pedersen L. Cardiovascular Risks of Diclofenac Versus Other Older COX-2 Inhibitors (Meloxicam and Etodolac) and Newer COX-2 Inhibitors (Celecoxib and Etoricoxib): A Series of Nationwide Emulated Trials. Drug Saf. 2022 Sep;45(9):983-994. doi: 10.1007/s40264-022-01211-1. Epub 2022 Jul 31. PMID: 35909207.

11: Farag M, Bahra A. Etoricoxib and celecoxib sensitive indomethacin-responsive headache disorders. Headache. 2022 Mar;62(3):383-388. doi: 10.1111/head.14282. Epub 2022 Mar 12. PMID: 35277974.

12: Martina SD, Vesta KS, Ripley TL. Etoricoxib: a highly selective COX-2 inhibitor. Ann Pharmacother. 2005 May;39(5):854-62. doi: 10.1345/aph.1E543. Epub 2005 Apr 12. PMID: 15827069.

13: Capone ML, Tacconelli S, Patrignani P. Clinical pharmacology of etoricoxib. Expert Opin Drug Metab Toxicol. 2005 Aug;1(2):269-82. doi: 10.1517/17425255.1.2.269. PMID: 16922642.

14: Ribeiro H, Rodrigues I, Napoleão L, Lira L, Marques D, Veríssimo M, Andrade JP, Dourado M. Non-steroidal anti-inflammatory drugs (NSAIDs), pain and aging: Adjusting prescription to patient features. Biomed Pharmacother. 2022 Jun;150:112958. doi: 10.1016/j.biopha.2022.112958. Epub 2022 Apr 19. PMID: 35453005.

15: Couto M, López-Salgueiro R, Gaspar Â. Anaphylaxis to Etoricoxib. J Investig Allergol Clin Immunol. 2018 Apr;28(2):135-136. doi: 10.18176/jiaci.0221. PMID: 29661743.

16: Croom KF, Siddiqui MA. Etoricoxib: a review of its use in the symptomatic treatment of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis and acute gouty arthritis. Drugs. 2009 Jul 30;69(11):1513-32. doi: 10.2165/00003495-200969110-00008. PMID: 19634927.

17: Clarke R, Derry S, Moore RA. Single dose oral etoricoxib for acute postoperative pain in adults. Cochrane Database Syst Rev. 2014 May 8;2014(5):CD004309. doi: 10.1002/14651858.CD004309.pub4. PMID: 24809657; PMCID: PMC6485336.

18: Wang R. Etoricoxib may inhibit cytokine storm to treat COVID-19. Med Hypotheses. 2021 May;150:110557. doi: 10.1016/j.mehy.2021.110557. Epub 2021 Mar 6. PMID: 33730601; PMCID: PMC7935670.

19: Clarke R, Derry S, Moore RA. Single dose oral etoricoxib for acute postoperative pain in adults. Cochrane Database Syst Rev. 2012 Apr 18;(4):CD004309. doi: 10.1002/14651858.CD004309.pub3. Update in: Cochrane Database Syst Rev. 2014;(5):CD004309. PMID: 22513922.

20: Thirion L, Nikkels AF, Piérard GE. Etoricoxib-induced erythema-multiforme- like eruption. Dermatology. 2008;216(3):227-8. doi: 10.1159/000112930. Epub 2008 Jan 9. PMID: 18182814.

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