Copper naproxen: Difference between revisions

Copper naproxen
	; Sample of copper naproxen in a glass vial
Names
	Other names Copper(II) 6-methoxy-a-methyl-2-naphthaleneacetate
Identifiers
Properties
Chemical formula	C28H26CuO6
Molar mass	522.056 g·mol−1
Appearance	Green solid
Solubility	Soluble in methanol, 1,4-dioxane, DMSO, DMF
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

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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]

${\ce {2C14H13NaO3 + CuSO4 -> C28H26CuO6 + Na2SO4}}$

References

^ ^a ^b ^c ^d 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.
^ ^a ^b 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.
^ 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, retrieved 2022-04-10
^ 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.
^ 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.

[Melnik-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.

[Dimiza-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, 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.

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@@ Line 1: / Line 1: @@
 {{Chembox
 | Name           = Copper naproxen
-| ImageFile      = Copper naproxen.svg
+| ImageFile      = Copper naproxen.jpg
+| ImageFile1     = Copper naproxen.svg
+| ImageCaption   = Sample of copper naproxen in a glass vial
 | OtherNames     = Copper(II) 6-methoxy-a-methyl-2-naphthaleneacetate
 | Section1       = {{Chembox Identifiers
@@ Line 34: / Line 36: @@
 | pKb =
 | Solubility =
-| SolubleOther = Soluble in [[methanol]], [[1,4-dioxane]]<ref name="Melnik" />, [[Dimethyl sulfoxide|DMSO]], [[2,5-Dimethylfuran|DMF]]<ref name="Dimiza" />
+| SolubleOther = Soluble in [[methanol]], [[1,4-dioxane]],<ref name="Melnik" /> [[Dimethyl sulfoxide|DMSO]], [[2,5-Dimethylfuran|DMF]]<ref name="Dimiza" />
   }}
 | Section3       = {{Chembox Structure
@@ Line 74: / Line 76: @@
 | Section8       = {{Chembox Related
 | OtherAnions =
-| OtherCompounds = [[Copper aspirinate]]</br>[[Copper ibuprofenate]]
+| OtherCompounds = [[Copper aspirinate]]<br />[[Copper ibuprofenate]]
   }}
 }}
-'''Copper naproxen''' is a [[Coordination complex|chemical complex]] of [[Copper|copper<sup>2+</sup>]] [[Chelation|chelated]] with the [[anti-inflammatory]] drug  [[naproxen]].<ref name="Melnik" /> Copper complexes of [[Nsaids|NSAIDs]] like naproxen have been shown to have greater anti-inflammatory properties than the base drug.<ref>{{Citation |last=Sorenson |first=John R.J. |title=6 Copper Complexes Offer a Physiological Approach to Treatment of Chronic Diseases |date=1989 |url=https://linkinghub.elsevier.com/retrieve/pii/S0079646808702467 |work=Progress in Medicinal Chemistry |volume=26 |pages=437–568 |publisher=Elsevier |language=en |doi=10.1016/s0079-6468(08)70246-7 |isbn=978-0-444-81038-0 |access-date=2022-04-10}}</ref><ref name="Dimiza">{{Cite journal |last=Dimiza |first=Filitsa |last2=Perdih |first2=Franc |last3=Tangoulis |first3=Vassilis |last4=Turel |first4=Iztok |last5=Kessissoglou |first5=Dimitris P. |last6=Psomas |first6=George |date=March 2011 |title=Interaction of copper(II) with the non-steroidal anti-inflammatory drugs naproxen and diclofenac: Synthesis, structure, DNA- and albumin-binding |url=https://linkinghub.elsevier.com/retrieve/pii/S0162013410002060 |journal=Journal of Inorganic Biochemistry |language=en |volume=105 |issue=3 |pages=476–489 |doi=10.1016/j.jinorgbio.2010.08.013}}</ref>
+'''Copper naproxen''' is a [[Coordination complex|chemical complex]] of [[Copper|copper<sup>2+</sup>]] [[Chelation|chelated]] with the [[anti-inflammatory]] drug  [[naproxen]].<ref name="Melnik" /> Copper complexes of [[Nsaids|NSAIDs]] like naproxen have been shown to have greater anti-inflammatory properties than the base drug.<ref>{{Citation |last=Sorenson |first=John R.J. |title=6 Copper Complexes Offer a Physiological Approach to Treatment of Chronic Diseases |date=1989 |url=https://linkinghub.elsevier.com/retrieve/pii/S0079646808702467 |series=Progress in Medicinal Chemistry |volume=26 |pages=437–568 |publisher=Elsevier |language=en |doi=10.1016/s0079-6468(08)70246-7 |isbn=978-0-444-81038-0 |access-date=2022-04-10}}</ref><ref name="Dimiza">{{Cite journal |last1=Dimiza |first1=Filitsa |last2=Perdih |first2=Franc |last3=Tangoulis |first3=Vassilis |last4=Turel |first4=Iztok |last5=Kessissoglou |first5=Dimitris P. |last6=Psomas |first6=George |date=March 2011 |title=Interaction of copper(II) with the non-steroidal anti-inflammatory drugs naproxen and diclofenac: Synthesis, structure, DNA- and albumin-binding |url=https://linkinghub.elsevier.com/retrieve/pii/S0162013410002060 |journal=Journal of Inorganic Biochemistry |language=en |volume=105 |issue=3 |pages=476–489 |doi=10.1016/j.jinorgbio.2010.08.013}}</ref>
-Copper naproxen can by found as a [[Hydrate|monohydrate]], and it can form complexes with other [[Organic compound|organic molecules]] such as [[nicotinyl alcohol]], [[3-Methylpyridine|3-methylpyridine]], and [[caffeine]].<ref name="Melnik" /><ref>{{Cite journal |last=Caglar |first=Sema |last2=Adiguzel |first2=Ekrem |last3=Sariboga |first3=Bahtiyar |last4=Temel |first4=Ersin |last5=Buyukgungor |first5=Orhan |date=2014-02-16 |title=Mono and dinuclear copper(II) naproxenato complexes containing 3-picoline and 4-picoline: synthesis, structure, properties, catechol oxidase, and antimicrobial activities |url=https://www.tandfonline.com/doi/full/10.1080/00958972.2014.891198 |journal=Journal of Coordination Chemistry |language=en |volume=67 |issue=4 |pages=670–683 |doi=10.1080/00958972.2014.891198 |issn=0095-8972}}</ref><ref>{{Cite journal |last=Abuhijleh |first=A. Latif |last2=Khalaf |first2=Juhienah |date=September 2010 |title=Copper (II) complexes of the anti-inflammatory drug naproxen and 3-pyridylmethanol as auxiliary ligand. Characterization, superoxide dismutase and catecholase – mimetic activities |url=https://linkinghub.elsevier.com/retrieve/pii/S0223523410003715 |journal=European Journal of Medicinal Chemistry |language=en |volume=45 |issue=9 |pages=3811–3817 |doi=10.1016/j.ejmech.2010.05.031}}</ref>
+Copper naproxen can be found as a [[Hydrate|monohydrate]], and it can form complexes with other [[Organic compound|organic molecules]] such as [[nicotinyl alcohol]], [[3-Methylpyridine|3-methylpyridine]], and [[caffeine]].<ref name="Melnik" /><ref>{{Cite journal |last1=Caglar |first1=Sema |last2=Adiguzel |first2=Ekrem |last3=Sariboga |first3=Bahtiyar |last4=Temel |first4=Ersin |last5=Buyukgungor |first5=Orhan |date=2014-02-16 |title=Mono and dinuclear copper(II) naproxenato complexes containing 3-picoline and 4-picoline: synthesis, structure, properties, catechol oxidase, and antimicrobial activities |url=https://www.tandfonline.com/doi/full/10.1080/00958972.2014.891198 |journal=Journal of Coordination Chemistry |language=en |volume=67 |issue=4 |pages=670–683 |doi=10.1080/00958972.2014.891198 |s2cid=96991445 |issn=0095-8972}}</ref><ref>{{Cite journal |last1=Abuhijleh |first1=A. Latif |last2=Khalaf |first2=Juhienah |date=September 2010 |title=Copper (II) complexes of the anti-inflammatory drug naproxen and 3-pyridylmethanol as auxiliary ligand. Characterization, superoxide dismutase and catecholase – mimetic activities |url=https://linkinghub.elsevier.com/retrieve/pii/S0223523410003715 |journal=European Journal of Medicinal Chemistry |language=en |volume=45 |issue=9 |pages=3811–3817 |doi=10.1016/j.ejmech.2010.05.031|pmid=20605277 }}</ref>
 == Preparation ==
-Copper naproxen is prepared by reacting sodium naproxen with a copper(II) salt such as [[copper(II) sulfate]].<ref name="Melnik">{{Cite journal |last=Melnı́k |first=Milan |last2=Macásková |first2=Lubov |last3=Holloway |first3=Clive E |last4=Mrozinski |first4=Jerzy |last5=Kalin’ska |first5=Bozena |date=March 2000 |title=Spectral and magnetic properties of copper(II) naproxenates |url=https://linkinghub.elsevier.com/retrieve/pii/S0020169399005046 |journal=Inorganica Chimica Acta |language=en |volume=299 |issue=2 |pages=284–287 |doi=10.1016/S0020-1693(99)00504-6}}</ref>
+Copper naproxen is prepared by reacting sodium naproxen with a copper(II) salt such as [[copper(II) sulfate]].<ref name="Melnik">{{Cite journal |last1=Melnı́k |first1=Milan |last2=Macásková |first2=Lubov |last3=Holloway |first3=Clive E |last4=Mrozinski |first4=Jerzy |last5=Kalin’ska |first5=Bozena |date=March 2000 |title=Spectral and magnetic properties of copper(II) naproxenates |url=https://linkinghub.elsevier.com/retrieve/pii/S0020169399005046 |journal=Inorganica Chimica Acta |language=en |volume=299 |issue=2 |pages=284–287 |doi=10.1016/S0020-1693(99)00504-6}}</ref>
 <chem>2C14H13NaO3 + CuSO4 -> C28H26CuO6 + Na2SO4</chem>
@@ Line 92: / Line 94: @@
 [[Category:Copper(II) compounds]]
 [[Category:Experimental drugs]]
+[[Category:Nonsteroidal anti-inflammatory drugs]]