Meclofenamic Acid | CAS#644-62-2

MedKoo Cat#: 318177 | Name: Meclofenamic Acid

Description:

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

Meclofenamic acid is a drug used for joint, muscular pain, arthritis and dysmenorrhea. Meclofenamic acid is a non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis. It is a member of the anthranilic acid derivatives class of NSAID drugs and was approved by the FDA in 1980. Like other members of the class, it is a COX inhibitor and prevents formation of prostaglandins.

Chemical Structure

Meclofenamic Acid

CAS#644-62-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 318177

Name: Meclofenamic Acid

CAS#: 644-62-2 (free acid)

Chemical Formula: C14H11Cl2NO2

Exact Mass: 295.0167

Molecular Weight: 296.15

Elemental Analysis: C, 56.78; H, 3.74; Cl, 23.94; N, 4.73; O, 10.80

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Related CAS #

6385-02-0 (sodium) 644-62-2 (free acid) 67254-91-5 (sodium hydrate)

Synonym

Meclofenamic Acid; Meclofenamate; Arquel; Meclophenamic acid; Meclomen;

IUPAC/Chemical Name

2-(2,6-dichloro-3-methylanilino)benzoic acid

InChi Key

SBDNJUWAMKYJOX-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H11Cl2NO2/c1-8-6-7-10(15)13(12(8)16)17-11-5-3-2-4-9(11)14(18)19/h2-7,17H,1H3,(H,18,19)

SMILES Code

CC1=C(C(=C(C=C1)Cl)NC2=CC=CC=C2C(=O)O)Cl

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:

Meclofenamic acid is a highly selective FTO (fat mass and obesity-associated) enzyme inhibitor. Meclofenamic acid inhibits hKv2.1 and hKv1.1, with IC50 values of 56.0 and 155.9 μM, respectively.

In vitro activity:

Meclofenamic acid inhibited hKv2.1 in a concentration-dependent manner whereas the other three fenamates had weaker or no effect on these channels at a concentration of 100 microM. The estimated IC50 of meclofenamic acid was 56.0 microM for hKv2.1 compared an IC50 of 155.9 microM for another human neuronal K channel (hKv1.1). Reference: Eur J Pharmacol. 1999 Aug 13;378(3):349-56. https://pubmed.ncbi.nlm.nih.gov/10493112/

In vivo activity:

Tumors were created in a nude mouse model using PC3 cancerous human cells. Meclofenamic acid (10 mg/kg/day; experimental group, n=5) or saline solution (control group, n=5) was administered intraperitoneally for twenty days. Meclofenamic acid causes histological changes that indicate less tumor aggression (less hypercellularity, fewer atypical mitoses, and fewer nuclear polymorphisms), an increase in fibrosis, and reduced cellular proliferation and tumor vascularity. Reference: Int Braz J Urol. 2015 Sep-Oct;41(5):1002-7. https://pubmed.ncbi.nlm.nih.gov/26689527/

Preparing Stock Solutions

The following data is based on the product molecular weight 296.15 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. Huang Y, Yan J, Li Q, Li J, Gong S, Zhou H, Gan J, Jiang H, Jia GF, Luo C, Yang CG. Meclofenamic acid selectively inhibits FTO demethylation of m6A over ALKBH5. Nucleic Acids Res. 2015 Jan;43(1):373-84. doi: 10.1093/nar/gku1276. Epub 2014 Dec 1. PMID: 25452335; PMCID: PMC4288171. 2. Lee YT, Wang Q. Inhibition of hKv2.1, a major human neuronal voltage-gated K+ channel, by meclofenamic acid. Eur J Pharmacol. 1999 Aug 13;378(3):349-56. doi: 10.1016/s0014-2999(99)00485-9. PMID: 10493112. 3. Delgado-Enciso I, Soriano-Hernández AD, Rodriguez-Hernandez A, Galvan-Salazar HR, Montes-Galindo DA, Martinez-Martinez R, Valdez-Velazquez LL, Gonzalez-Alvarez R, Espinoza-Gómez F, Newton-Sanchez OA, Lara-Esqueda A, Guzman-Esquivel J. Histological changes caused by meclofenamic acid in androgen-independent prostate cancer tumors: evaluation in a mouse model. Int Braz J Urol. 2015 Sep-Oct;41(5):1002-7. doi: 10.1590/S1677-5538.IBJU.2013.00186. PMID: 26689527; PMCID: PMC4756978. 4. Soriano-Hernandez AD, Madrigal-Pérez D, Galvan-Salazar HR, Martinez-Fierro ML, Valdez-Velazquez LL, Espinoza-Gómez F, Vazquez-Vuelvas OF, Olmedo-Buenrostro BA, Guzman-Esquivel J, Rodriguez-Sanchez IP, Lara-Esqueda A, Montes-Galindo DA, Delgado-Enciso I. Anti-inflammatory drugs and uterine cervical cancer cells: Antineoplastic effect of meclofenamic acid. Oncol Lett. 2015 Oct;10(4):2574-2578. doi: 10.3892/ol.2015.3580. Epub 2015 Aug 7. PMID: 26622892; PMCID: PMC4580029.

In vitro protocol:

In vivo protocol:

1. Delgado-Enciso I, Soriano-Hernández AD, Rodriguez-Hernandez A, Galvan-Salazar HR, Montes-Galindo DA, Martinez-Martinez R, Valdez-Velazquez LL, Gonzalez-Alvarez R, Espinoza-Gómez F, Newton-Sanchez OA, Lara-Esqueda A, Guzman-Esquivel J. Histological changes caused by meclofenamic acid in androgen-independent prostate cancer tumors: evaluation in a mouse model. Int Braz J Urol. 2015 Sep-Oct;41(5):1002-7. doi: 10.1590/S1677-5538.IBJU.2013.00186. PMID: 26689527; PMCID: PMC4756978. 2. Soriano-Hernandez AD, Madrigal-Pérez D, Galvan-Salazar HR, Martinez-Fierro ML, Valdez-Velazquez LL, Espinoza-Gómez F, Vazquez-Vuelvas OF, Olmedo-Buenrostro BA, Guzman-Esquivel J, Rodriguez-Sanchez IP, Lara-Esqueda A, Montes-Galindo DA, Delgado-Enciso I. Anti-inflammatory drugs and uterine cervical cancer cells: Antineoplastic effect of meclofenamic acid. Oncol Lett. 2015 Oct;10(4):2574-2578. doi: 10.3892/ol.2015.3580. Epub 2015 Aug 7. PMID: 26622892; PMCID: PMC4580029.

1: Soriano-Hernandez AD, Madrigal-Pérez D, Galvan-Salazar HR, Martinez-Fierro ML, Valdez-Velazquez LL, Espinoza-Gómez F, Vazquez-Vuelvas OF, Olmedo-Buenrostro BA, Guzman-Esquivel J, Rodriguez-Sanchez IP, Lara-Esqueda A, Montes-Galindo DA, Delgado-Enciso I. Anti-inflammatory drugs and uterine cervical cancer cells: Antineoplastic effect of meclofenamic acid. Oncol Lett. 2015 Oct;10(4):2574-2578. Epub 2015 Aug 7. PubMed PMID: 26622892; PubMed Central PMCID: PMC4580029. 2: Delgado-Enciso I, Soriano-Hernández AD, Rodriguez-Hernandez A, Galvan-Salazar HR, Montes-Galindo DA, Martinez-Martinez R, Valdez-Velazquez LL, Gonzalez-Alvarez R, Espinoza-Gómez F, Newton-Sanchez OA, Lara-Esqueda A, Guzman-Esquivel J. Histological changes caused by meclofenamic acid in androgen-independent prostate cancer tumors: evaluation in a mouse model. Int Braz J Urol. 2015 Sep-Oct;41(5):1002-7. doi: 10.1590/S1677-5538.IBJU.2013.00186. PubMed PMID: 26689527. 3: Huang Y, Yan J, Li Q, Li J, Gong S, Zhou H, Gan J, Jiang H, Jia GF, Luo C, Yang CG. Meclofenamic acid selectively inhibits FTO demethylation of m6A over ALKBH5. Nucleic Acids Res. 2015 Jan;43(1):373-84. doi: 10.1093/nar/gku1276. Epub 2014 Dec 1. PubMed PMID: 25452335; PubMed Central PMCID: PMC4288171. 4: Sun H, Wen Y, Ning N, An J, Li J. Retinal toxicity associated with high dose of meclofenamic acid. Drug Chem Toxicol. 2013 Oct;36(4):461-5. doi: 10.3109/01480545.2013.776582. Epub 2013 Mar 27. PubMed PMID: 23534549. 5: Ning N, Wen Y, Li Y, Li J. Meclofenamic acid blocks the gap junction communication between the retinal pigment epithelial cells. Hum Exp Toxicol. 2013 Nov;32(11):1164-9. doi: 10.1177/0960327112472997. Epub 2013 Apr 12. PubMed PMID: 23584353. 6: Jin M, Dai Y, Xu C, Wang Y, Wang S, Chen Z. Effects of meclofenamic acid on limbic epileptogenesis in mice kindling models. Neurosci Lett. 2013 May 24;543:110-4. doi: 10.1016/j.neulet.2013.03.029. Epub 2013 Apr 6. PubMed PMID: 23567745. 7: Soriano-Hernández AD, Galvan-Salazar HR, Montes-Galindo DA, Rodriguez-Hernandez A, Martinez-Martinez R, Guzman-Esquivel J, Valdez-Velazquez LL, Baltazar-Rodriguez LM, Espinoza-Gómez F, Rojas-Martinez A, Ortiz-Lopez R, Gonzalez-Alvarez R, Delgado-Enciso I. Antitumor effect of meclofenamic acid on human androgen-independent prostate cancer: a preclinical evaluation. Int Urol Nephrol. 2012 Apr;44(2):471-7. doi: 10.1007/s11255-011-0012-0. Epub 2011 Jun 10. PubMed PMID: 21660425. 8: Kovala-Demertzi D, Staninska M, Garcia-Santos I, Castineiras A, Demertzis MA. Synthesis, crystal structures and spectroscopy of meclofenamic acid and its metal complexes with manganese(II), copper(II), zinc(II) and cadmium(II). Antiproliferative and superoxide dismutase activity. J Inorg Biochem. 2011 Sep;105(9):1187-95. doi: 10.1016/j.jinorgbio.2011.05.025. Epub 2011 Jun 13. PubMed PMID: 21718655. 9: Sauter A, Landers A, Dittmann H, Pritzkow M, Wiesinger B, Bayer M, Bantleon R, Schmehl J, Claussen CD, Kehlbach R. A dual-inhibition study on vascular smooth muscle cells with meclofenamic acid and β-irradiation for the prevention of restenosis. J Vasc Interv Radiol. 2011 May;22(5):623-9. doi: 10.1016/j.jvir.2010.12.015. Epub 2011 Mar 17. PubMed PMID: 21414804. 10: Pygall SR, Griffiths PC, Wolf B, Timmins P, Melia CD. Solution interactions of diclofenac sodium and meclofenamic acid sodium with hydroxypropyl methylcellulose (HPMC). Int J Pharm. 2011 Feb 28;405(1-2):55-62. doi: 10.1016/j.ijpharm.2010.11.043. Epub 2010 Dec 1. PubMed PMID: 21129466. 11: Kovala-Demertzi D, Dokorou V, Primikiri A, Vargas R, Silvestru C, Russo U, Demertzis MA. Organotin meclofenamic complexes: Synthesis, crystal structures and antiproliferative activity of the first complexes of meclofenamic acid - novel anti-tuberculosis agents. J Inorg Biochem. 2009 May;103(5):738-44. doi: 10.1016/j.jinorgbio.2009.01.014. Epub 2009 Jan 27. PubMed PMID: 19237201. 12: Veruki ML, Hartveit E. Meclofenamic acid blocks electrical synapses of retinal AII amacrine and on-cone bipolar cells. J Neurophysiol. 2009 May;101(5):2339-47. doi: 10.1152/jn.00112.2009. Epub 2009 Mar 11. PubMed PMID: 19279153. 13: Popot MA, Menaut L, Boyer S, Bonnaire Y, Toutain PL. Spurious urine excretion drug profile in the horse due to bedding contamination and drug recycling: the case of meclofenamic acid. J Vet Pharmacol Ther. 2007 Apr;30(2):179-84. PubMed PMID: 17348907. 14: Kadiiska MB, Gladen BC, Baird DD, Graham LB, Parker CE, Ames BN, Basu S, Fitzgerald GA, Lawson JA, Marnett LJ, Morrow JD, Murray DM, Plastaras J, Roberts LJ 2nd, Rokach J, Shigenaga MK, Sun J, Walter PB, Tomer KB, Barrett JC, Mason RP. Biomarkers of oxidative stress study III. Effects of the nonsteroidal anti-inflammatory agents indomethacin and meclofenamic acid on measurements of oxidative products of lipids in CCl4 poisoning. Free Radic Biol Med. 2005 Mar 15;38(6):711-8. PubMed PMID: 15721981. 15: Kalgutkar AS, Rowlinson SW, Crews BC, Marnett LJ. Amide derivatives of meclofenamic acid as selective cyclooxygenase-2 inhibitors. Bioorg Med Chem Lett. 2002 Feb 25;12(4):521-4. PubMed PMID: 11844663. 16: Lee YT, Wang Q. Inhibition of hKv2.1, a major human neuronal voltage-gated K+ channel, by meclofenamic acid. Eur J Pharmacol. 1999 Aug 13;378(3):349-56. PubMed PMID: 10493112. 17: Stadler I, Chadha KC, Nakeeb S, Toumbis C, Butsch J, Mathur N, Munschauer F, Vladutiu A, Satchidanand SK, Ambrus JL. Pentoxifylline and meclofenamic acid treatment reduces clinical manifestations in a murine model of AIDS. J Pharmacol Exp Ther. 1994 Jan;268(1):10-3. PubMed PMID: 8301544. 18: Johansson IM, Kallings P, Hammarlund-Udenaes M. Studies of meclofenamic acid and two metabolites in horses--pharmacokinetics and effects on exercise tolerance. J Vet Pharmacol Ther. 1991 Sep;14(3):235-42. PubMed PMID: 1744932. 19: Vecchiet L, Colozzi A. Effects of meclofenamic acid in the treatment of lesions deriving from minor traumatology. Clin J Pain. 1991;7 Suppl 1:S54-9. PubMed PMID: 1810522. 20: Mitchell ES, McKellar QA, Bogan JA. Effect of meclofenamic acid on the response of parasite-naive lambs and adult sheep to Ostertagia circumcincta. Res Vet Sci. 1990 Sep;49(2):166-70. PubMed PMID: 2236912.