Copper naproxen

Copper naproxen

Sample of copper naproxen in a glass vial
Names
Other names Copper(II) 6-methoxy-a-methyl-2-naphthaleneacetate
Identifiers
3D model (JSmol)	Interactive image
InChI InChI=1S/2C14H14O3.Cu/c2*1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10;/h2*3-9H,1-2H3,(H,15,16);/q;;+2/p-2/t2*9-;/m00./s1 Key: GBARQYVMLWJLEP-NAWJVIAPSA-L
SMILES COc1cc2ccc(cc2cc1)[C@H](C)C(=O)[O-].COc1cc2ccc(cc2cc1)[C@H](C)C(=O)[O-].[Cu+2]
Properties
Chemical formula	C28H26CuO6
Molar mass	522.056 g·mol−1
Appearance	Green solid
Solubility	Soluble in methanol, 1,4-dioxane, [1] DMSO, DMF [2]
Related compounds
Related compounds	Copper aspirinate Copper ibuprofenate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Copper naproxen is a chemical complex of copper²⁺ chelated with the anti-inflammatory drug naproxen. ^[1] Copper complexes of NSAIDs like naproxen have been shown to have greater anti-inflammatory properties than the base drug. ^{[3] [2]}

Copper naproxen can be found as a monohydrate, and it can form complexes with other organic molecules such as nicotinyl alcohol, 3-methylpyridine, and caffeine. ^{[1] [4] [5]}

Preparation

Copper naproxen is prepared by reacting sodium naproxen with a copper(II) salt such as copper(II) sulfate. ^[1]

2 C₁₄H₁₃NaO₃ + CuSO₄ → C₂₈H₂₆CuO₆ + Na₂SO₄

References

1. Melnı́k, Milan; Macásková, Lubov; Holloway, Clive E; Mrozinski, Jerzy; Kalin’ska, Bozena (March 2000). "Spectral and magnetic properties of copper(II) naproxenates" . Inorganica Chimica Acta. 299 (2): 284–287. doi:10.1016/S0020-1693(99)00504-6.
2. Dimiza, Filitsa; Perdih, Franc; Tangoulis, Vassilis; Turel, Iztok; Kessissoglou, Dimitris P.; Psomas, George (March 2011). "Interaction of copper(II) with the non-steroidal anti-inflammatory drugs naproxen and diclofenac: Synthesis, structure, DNA- and albumin-binding" . Journal of Inorganic Biochemistry. 105 (3): 476–489. doi:10.1016/j.jinorgbio.2010.08.013.
3. Sorenson, John R.J. (1989), 6 Copper Complexes Offer a Physiological Approach to Treatment of Chronic Diseases , Progress in Medicinal Chemistry, vol. 26, Elsevier, pp. 437–568, doi:10.1016/s0079-6468(08)70246-7, ISBN   978-0-444-81038-0, PMID   2690187 , retrieved 2022-04-10
4. Caglar, Sema; Adiguzel, Ekrem; Sariboga, Bahtiyar; Temel, Ersin; Buyukgungor, Orhan (2014-02-16). "Mono and dinuclear copper(II) naproxenato complexes containing 3-picoline and 4-picoline: synthesis, structure, properties, catechol oxidase, and antimicrobial activities" . Journal of Coordination Chemistry. 67 (4): 670–683. doi:10.1080/00958972.2014.891198. ISSN   0095-8972. S2CID   96991445.
5. Abuhijleh, A. Latif; Khalaf, Juhienah (September 2010). "Copper (II) complexes of the anti-inflammatory drug naproxen and 3-pyridylmethanol as auxiliary ligand. Characterization, superoxide dismutase and catecholase – mimetic activities" . European Journal of Medicinal Chemistry. 45 (9): 3811–3817. doi:10.1016/j.ejmech.2010.05.031. PMID   20605277.