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MedKoo Cat#: 317855 | Name: Etodolac
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Description:

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

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

Theoretical Analysis

MedKoo Cat#: 317855

Name: Etodolac

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

Chemical Formula: C17H21NO3

Exact Mass: 287.1521

Molecular Weight: 287.35

Elemental Analysis: C, 71.06; H, 7.37; N, 4.87; O, 16.70

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
25g USD 550.00 2 Weeks
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Related CAS #
150975-87-4 (sodium) 79541-43-8 (Acyl Glucuronide) 41340-25-4 (free base)
Synonym
Etodolac; (±)-Etodolac; Etodolic Acid; Lodine; Ramodar; Ultradol; NSC 282126; NSC282126; NSC-282126; AY 24,236; AY24,236; AY-24,236; AY-24236; AY 24236; AY24236;
IUPAC/Chemical Name
2-(1,8-diethyl-1,3,4,9-tetrahydropyrano[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
View handling instruction
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/
Solvent mg/mL 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
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

Recalculate based on batch purity %
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.
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.