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 C
14H
13NaO
3 \+ CuSO
4 → C
28H
26CuO
6 \+ Na
2SO

## References

1. ↑ 1.0 1.1 1.2 1.3 Melnı́k, Milan; Macásková, Lubov; Holloway, Clive E; Mrozinski, Jerzy; Kalin’ska, Bozena (March 2000). "Spectral and magnetic properties of copper(II) naproxenates" (in en). Inorganica Chimica Acta 299 (2): 284–287. doi:10.1016/S0020-1693(99)00504-6. https://linkinghub.elsevier.com/retrieve/pii/S0020169399005046.
2. ↑ 2.0 2.1 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" (in en). Journal of Inorganic Biochemistry 105 (3): 476–489. doi:10.1016/j.jinorgbio.2010.08.013. https://linkinghub.elsevier.com/retrieve/pii/S0162013410002060.
3. ↑ Sorenson, John R.J. (1989) (in en), 6 Copper Complexes Offer a Physiological Approach to Treatment of Chronic Diseases, Progress in Medicinal Chemistry, 26, Elsevier, pp. 437–568, doi:10.1016/s0079-6468(08)70246-7, ISBN 978-0-444-81038-0, PMID 2690187, https://linkinghub.elsevier.com/retrieve/pii/S0079646808702467, 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" (in en). Journal of Coordination Chemistry 67 (4): 670–683. doi:10.1080/00958972.2014.891198. ISSN 0095-8972. https://www.tandfonline.com/doi/full/10.1080/00958972.2014.891198.
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" (in en). European Journal of Medicinal Chemistry 45 (9): 3811–3817. doi:10.1016/j.ejmech.2010.05.031. PMID 20605277. https://linkinghub.elsevier.com/retrieve/pii/S0223523410003715.

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