Etodolac | CAS#41340-25-4 | Anti-inflammatory

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

MedKoo CAT#: 317855

CAS#: 41340-25-4 (free base)

Description: Etodolac is a nonsteroidal anti-inflammatory drug (NSAID). Etodolac blocks the cyclooxygenase (COX) enzymes resulting in lower concentrations of prostaglandins. Consequently, inflammation, pain and fever are reduced.

Chemical Structure

Etodolac

CAS# 41340-25-4 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317855
Name: Etodolac
CAS#: 41340-25-4 (free base)
Chemical Formula: C17H21NO3
Exact Mass: 287.15
Molecular Weight: 287.354
Elemental Analysis: C, 71.06; H, 7.37; N, 4.87; O, 16.70

Price and Availability

Size	Price	Availability
5g	USD 350	2 weeks
25g	USD 550	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.

Synonym: Etodolac, AY 24,236, AY 24236, AY-24,236, AY-24236, AY24,236, AY24236, Etodolic Acid, Lodine, Ramodar, Ultradol

IUPAC/Chemical Name: (RS)-2-(1,8-Diethyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl)acetic acid

InChi Key: NNYBQONXHNTVIJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)

SMILES Code: O=C(O)CC1(CC)OCCC2=C1NC3=C2C=CC=C3CC

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:	Etodolac (AY-24236) is a non-steroidal anti-inflammatory compound that is a non-selective inhibitor of COX (IC50=53.5 nM).
In vitro activity:	Pretreatment of cells with selective COX-2 blocker etodolac markedly inhibited ICl,vol activation by TNFα as well as subsequent apoptotic events such as apoptotic cell volume decrease (AVD) and elevation of caspase-3/7 activity. In contrast, a COX-1 blocker had no effect on the decrease in cell volume or the increase in caspase-3/7 activity induced by TNFα. Thus, the COX-2-selective blocker had an inhibitory effect on TNFα-induced apoptotic events, which suggests that this drug would have efficacy for the treatment of OA. Reference: Int J Mol Sci. 2013 Sep 30;14(10):19705-15. https://pubmed.ncbi.nlm.nih.gov/24084720/
In vivo activity:	The occurrence rates of biliary neoplasm were 43.8 and 15.2% in the control and etodolac groups, respectively (p < 0.05). The incidence of hamster biliary neoplasm increased as time progressed in the control group, whereas it remained at a low level throughout the experimental period in the etodolac group. PGE2 products tended to be lower in the etodolac group, and PCNA-LI was significantly lower in the etodolac group (p < 0.01). These results suggest that the medication etodolac suppresses cell proliferation of the biliary epithelium, thereby preventing biliary carcinogenesis. Reference: Eur Surg Res. 2014;52(1-2):73-82. https://pubmed.ncbi.nlm.nih.gov/24819958/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	62.7	218.09
	DMF	30.0	104.40
	Ethanol	39.0	135.72
	PBS (pH 7.2)	0.3	0.87

Preparing Stock Solutions

The following data is based on the product molecular weight 287.35 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. Kumagai K, Kubo M, Imai S, Toyoda F, Maeda T, Okumura N, Matsuura H, Matsusue Y. The COX-2 selective blocker etodolac inhibits TNFα-induced apoptosis in isolated rabbit articular chondrocytes. Int J Mol Sci. 2013 Sep 30;14(10):19705-15. doi: 10.3390/ijms141019705. PMID: 24084720; PMCID: PMC3821581. 2. Wang S, Dai Y, Kogure Y, Yamamoto S, Zhang W, Noguchi K. Etodolac activates and desensitizes transient receptor potential ankyrin 1. J Neurosci Res. 2013 Dec;91(12):1591-8. doi: 10.1002/jnr.23274. Epub 2013 Aug 30. PMID: 24027177. 3. Kitasato A, Kuroki T, Adachi T, Ono S, Tanaka T, Tsuneoka N, Hirabaru M, Takatsuki M, Eguchi S. A selective cyclooxygenase-2 inhibitor (Etodolac) prevents spontaneous biliary tumorigenesis in a hamster bilioenterostomy model. Eur Surg Res. 2014;52(1-2):73-82. doi: 10.1159/000362542. Epub 2014 May 8. PMID: 24819958. 4. Ito S, Tajima K, Nogawa M, Inoue N, Kyoi T, Takahashi Y, Sasagawa T, Nakamura A, Kotera T, Ueda M, Yamashita Y, Banno K. Etodolac, a cyclooxygenase-2 inhibitor, attenuates paclitaxel-induced peripheral neuropathy in a mouse model of mechanical allodynia. J Pharmacol Exp Ther. 2012 Jul;342(1):53-60. doi: 10.1124/jpet.111.187401. Epub 2012 Mar 29. PMID: 22460833.
In vitro protocol:	1. Kumagai K, Kubo M, Imai S, Toyoda F, Maeda T, Okumura N, Matsuura H, Matsusue Y. The COX-2 selective blocker etodolac inhibits TNFα-induced apoptosis in isolated rabbit articular chondrocytes. Int J Mol Sci. 2013 Sep 30;14(10):19705-15. doi: 10.3390/ijms141019705. PMID: 24084720; PMCID: PMC3821581. 2. Wang S, Dai Y, Kogure Y, Yamamoto S, Zhang W, Noguchi K. Etodolac activates and desensitizes transient receptor potential ankyrin 1. J Neurosci Res. 2013 Dec;91(12):1591-8. doi: 10.1002/jnr.23274. Epub 2013 Aug 30. PMID: 24027177.
In vivo protocol:	1. Kitasato A, Kuroki T, Adachi T, Ono S, Tanaka T, Tsuneoka N, Hirabaru M, Takatsuki M, Eguchi S. A selective cyclooxygenase-2 inhibitor (Etodolac) prevents spontaneous biliary tumorigenesis in a hamster bilioenterostomy model. Eur Surg Res. 2014;52(1-2):73-82. doi: 10.1159/000362542. Epub 2014 May 8. PMID: 24819958. 2. Ito S, Tajima K, Nogawa M, Inoue N, Kyoi T, Takahashi Y, Sasagawa T, Nakamura A, Kotera T, Ueda M, Yamashita Y, Banno K. Etodolac, a cyclooxygenase-2 inhibitor, attenuates paclitaxel-induced peripheral neuropathy in a mouse model of mechanical allodynia. J Pharmacol Exp Ther. 2012 Jul;342(1):53-60. doi: 10.1124/jpet.111.187401. Epub 2012 Mar 29. PMID: 22460833.

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1: Tirunagari SK, Derry S, Moore RA, McQuay HJ. Single dose oral etodolac for acute postoperative pain in adults. Cochrane Database Syst Rev. 2009 Jul 8;(3):CD007357. doi: 10.1002/14651858.CD007357.pub2. Review. PubMed PMID: 19588426; PubMed Central PMCID: PMC4164827.

2: Chen YF, Jobanputra P, Barton P, Bryan S, Fry-Smith A, Harris G, Taylor RS. Cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs (etodolac, meloxicam, celecoxib, rofecoxib, etoricoxib, valdecoxib and lumiracoxib) for osteoarthritis and rheumatoid arthritis: a systematic review and economic evaluation. Health Technol Assess. 2008 Apr;12(11):1-278, iii. Review. PubMed PMID: 18405470.

3: Dvornik DM. Tissue selective inhibition of prostaglandin biosynthesis by etodolac. J Rheumatol Suppl. 1997 Feb;47:40-7. Review. PubMed PMID: 9035019.

4: Brocks DR, Jamali F. Etodolac clinical pharmacokinetics. Clin Pharmacokinet. 1994 Apr;26(4):259-74. Review. PubMed PMID: 8013160.

5: Veys EM. Clinical performance of etodolac in patients with osteoarthritis and rheumatoid arthritis. Eur J Rheumatol Inflamm. 1994;14(1):23-7. Review. PubMed PMID: 7744125.

6: Benet LZ. Pharmacokinetics of sustained-release etodolac. Rheumatol Int. 1993;13(2 Suppl):S3-5. Review. PubMed PMID: 8210922.

7: Balfour JA, Buckley MM. Etodolac. A reappraisal of its pharmacology and therapeutic use in rheumatic diseases and pain states. Drugs. 1991 Aug;42(2):274-99. Review. PubMed PMID: 1717225.

8: Pena M. Etodolac: analgesic effects in musculoskeletal and postoperative pain. Rheumatol Int. 1990;10 Suppl:9-16. Review. PubMed PMID: 2150571.

9: Bacon PA. Etodolac: efficacy in osteoarthritis and effects on chondrocyte function. Rheumatol Int. 1990;10 Suppl:3-7. Review. PubMed PMID: 2150570.

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