Acemetacin
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MedKoo CAT#: 571503

CAS#: 53164-05-9

Description: Acemetacin is a non-steroidal anti-inflammatory drug . In bioactive situations it biotransforms to indomethacin to act as an analgesic.


Chemical Structure

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Acemetacin
CAS# 53164-05-9

Theoretical Analysis

MedKoo Cat#: 571503
Name: Acemetacin
CAS#: 53164-05-9
Chemical Formula: C21H18ClNO6
Exact Mass: 415.0823
Molecular Weight: 415.83
Elemental Analysis: C, 60.66; H, 4.36; Cl, 8.53; N, 3.37; O, 23.09

Price and Availability

Size Price Availability Quantity
5.0g USD 250.0 2 Weeks
25.0g USD 600.0 2 Weeks
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Synonym: Acemetacin; Rantudil; K 708; K-708; K708

IUPAC/Chemical Name: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, carboxymethyl ester

InChi Key: FSQKKOOTNAMONP-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H18ClNO6/c1-12-16(10-20(26)29-11-19(24)25)17-9-15(28-2)7-8-18(17)23(12)21(27)13-3-5-14(22)6-4-13/h3-9H,10-11H2,1-2H3,(H,24,25)

SMILES Code: O=C(OCC(O)=O)CC1=C(C)N(C(C2=CC=C(Cl)C=C2)=O)C3=C1C=C(OC)C=C3

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 415.83 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

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1: Sanphui P, Bolla G, Nangia A, Chernyshev V. Acemetacin cocrystals and salts: structure solution from powder X-ray data and form selection of the piperazine salt. IUCrJ. 2014 Feb 28;1(Pt 2):136-50. doi: 10.1107/S2052252514004229. eCollection 2014 Mar 1. PubMed PMID: 25075330; PubMed Central PMCID: PMC4062091.

2: Shehata TM, Abdallah MH, Ibrahim MM. Proniosomal oral tablets for controlled delivery and enhanced pharmacokinetic properties of acemetacin. AAPS PharmSciTech. 2015 Apr;16(2):375-83. doi: 10.1208/s12249-014-0233-5. Epub 2014 Oct 16. PubMed PMID: 25319057; PubMed Central PMCID: PMC4370976.

3: Cebeci F, Yaşar Ş, Aytekin S, Güneş P. Acemetacin-induced fixed drug eruption. Indian J Pharmacol. 2016 Mar-Apr;48(2):219-20. doi: 10.4103/0253-7613.178824. PubMed PMID: 27114641; PubMed Central PMCID: PMC4825444.

4: Gil-Flores M, Ortiz MI, Castañeda-Hernández G, Chávez-Piña AE. Acemetacin antinociceptive mechanism is not related to NO or K+ channel pathways. Methods Find Exp Clin Pharmacol. 2010 Mar;32(2):101-5. doi: 10.1358/mf.2010.32.2.1423883. PubMed PMID: 20401346.

5: Aybaba C, Palabiyik IM, Caglayan MG, Onur F. Multivariate optimization of separation conditions for simultaneous determination of acemetacin and chlorzoxazone in a pharmaceutical preparation by HPLC using response surface methodology. J AOAC Int. 2013 Jul-Aug;96(4):723-9. PubMed PMID: 24000743.

6: Moore RA, Derry S, McQuay HJ. Single dose oral acemetacin for acute postoperative pain in adults. Cochrane Database Syst Rev. 2009 Jul 8;(3):CD007589. doi: 10.1002/14651858.CD007589.pub2. Review. PubMed PMID: 19588437; PubMed Central PMCID: PMC4170991.

7: Chávez-Piña AE, Favari L, Castañeda-Hernández G. Pharmacokinetics of acemetacin and its active metabolite indomethacin in rats during acute hepatic damage and liver regeneration. Ann Hepatol. 2009 Apr-Jun;8(2):141-7. PubMed PMID: 19502658.

8: Ortiz MI, Ponce-Monter H, Fernández-Martínez E, Pérez-Hernández N, Macías A, Rangel-Flores E, Castañeda-Hernández G. Evaluation of the interaction between acemetacin and opioids on the hargreaves model of thermal hyperalgesia. Pharmacol Biochem Behav. 2007 Nov;88(1):47-54. Epub 2007 Jul 18. PubMed PMID: 17698180.

9: Badia-Flores J, Muñoz Barradas F. [Treatment of chronic polyarthritis with acemetacin and indomethacin]. Arzneimittelforschung. 1980;30(8A):1433-7. German. PubMed PMID: 7191311.

10: Dell HD, Doersing M, Fischer W, Jacobi H, Kamp R, Köhler G, Schöllnhammer G. [Metabolism and pharmacokinetics of acemetacin in man (author's transl)]. Arzneimittelforschung. 1980;30(8A):1391-8. German. PubMed PMID: 7191306.

11: Chávez-Piña AE, McKnight W, Dicay M, Castañeda-Hernández G, Wallace JL. Mechanisms underlying the anti-inflammatory activity and gastric safety of acemetacin. Br J Pharmacol. 2007 Nov;152(6):930-8. Epub 2007 Sep 17. PubMed PMID: 17876306; PubMed Central PMCID: PMC2078220.

12: Tavares IA, Bennett A. Acemetacin and indomethacin: differential inhibition of constitutive and inducible cyclo-oxygenases in human gastric mucosa and leucocytes. Int J Tissue React. 1993;15(2):49-53. PubMed PMID: 8144313.

13: Saul PA, Korlipara K. Acemetacin and indomethacin in the treatment of rheumatoid arthritis: a double-blind comparative study in general practice. Curr Med Res Opin. 1991;12(5):332-41. PubMed PMID: 2004546.

14: Gallacchi G, Hodinka L. [Randomized, double blind, multicentre, parallel group study to compare efficacy and safety of acemetacin and indometacin in patients with activated osteoarthrosis of the knee]. Praxis (Bern 1994). 2009 Jun 10;98(12):635-42. doi: 10.1024/1661-8157.98.12.635. German. PubMed PMID: 19513973.

15: Hazleman B, Bernstein RM. Acemetacin in the long-term therapy of rheumatoid arthritis. Curr Med Res Opin. 1993;13(2):119-26. PubMed PMID: 8325042.

16: Jacobi H, Dell HD. [On the pharmacodynamics of acemetacin (author's transl)]. Arzneimittelforschung. 1980;30(8A):1348-62. German. PubMed PMID: 6968219.

17: Gierse H, Eisebitt R, Bernard I. [Prevention of periarticular ossification--with results of a randomized, double-blind study comparing acemetacin versus indomethacin]. Z Orthop Ihre Grenzgeb. 1997 Sep-Oct;135(5):417-21. German. PubMed PMID: 9446434.

18: Neugirg R, Penners R. [Clinical trials with acemetacin on children and adolescents (author's transl)]. Arzneimittelforschung. 1980;30(8A):1451-4. German. PubMed PMID: 7191316.

19: Handrich L. [Comparison of the therapeutic efficacy and tolerability of acemetacin and tolmetin (author's transl)]. Arzneimittelforschung. 1980;30(8A):1448-51. German. PubMed PMID: 7191315.

20: Chávez-Piña AE, Vong L, McKnight W, Dicay M, Zanardo RC, Ortiz MI, Castañeda-Hernández G, Wallace JL. Lack of effects of acemetacin on signalling pathways for leukocyte adherence may explain its gastrointestinal safety. Br J Pharmacol. 2008 Nov;155(6):857-64. doi: 10.1038/bjp.2008.316. Epub 2008 Aug 11. PubMed PMID: 18695646; PubMed Central PMCID: PMC2597236.