Copper ibuprofenate

Copper ibuprofenate
	Anhydrous
	Monohydrate
	R = (CH3)2CHCH2C6H4CH(CH3)-
Names
	IUPAC name bis[2-(4-isobutylphenyl)propionato]copper(II)
Identifiers
CAS Number	66840-44-6 ;
3D model (JSmol)	Interactive image;
PubChem CID	23978;
CompTox Dashboard (EPA)	DTXSID201029390 ;
	InChI InChI=1S/4C13H17O2.2Cu/c41-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15;;/h44-7,9-10H,8H2,1-3H3;;/q4-3;2+6 Key: HEFOJHHJEKPEDO-UHFFFAOYSA-N;
	SMILES c0cc(CC(C)C)ccc0C(C)C-OCu+2(OC-C(C)c0ccc(CC(C)C)cc0)OC-C(C)c0ccc(CC(C)C)cc0;
Properties
Chemical formula	C52H68Cu2O8
Molar mass	948.200 g·mol−1
Appearance	Blue Powder
Density	1.299 g/cm3
Solubility in water	Slightly soluble
Solubility in isopropanol	Slightly soluble
Related compounds
Other anions	Copper aspirinate
Related compounds	Ibuprofen
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Copper ibuprofenate is a coordination complex consisting of copper(II) and the conjugate base of ibuprofen.

Structure

Copper ibuprofenate adopts a typical Chinese lantern structure, as seen for many transition metal carboxylate complexes. X-ray crystallography reveals a polymer with a bonding motif very similar to that of copper(II) trifluoroacetate.^[1]

Preparation

The compound is prepared by the reaction of sodium ibuprofenate with copper(II) sulfate.^[2]^[3]

Uses

It has been suggested that copper complexes of anti-inflammatory drugs are more active than the parent drug^[4] and produce fewer gastrointestinal side-effects.^[5]

In 2008, a United States patent was issued for the utilization of ibuprofenate complexes (including copper ibuprofenate) as a wood preservative.^[6]

References

^ ^a ^b Lippi, Martina; Paoli, Paola; Conti, Luca; Giacomazzo, Gina Elena; MacEdi, Eleonora; Ceccarelli, Jacopo; Missina, Juliana Morais; Fagorzi, Camilla; Rossi, Patrizia (2024). "Ibuprofen: A multi-purpose active pharmaceutical ingredient as versatile ligand for zinc(II) and copper(II). Solid state and solution studies". Inorganica Chimica Acta. 566 122034. doi:10.1016/j.ica.2024.122034. hdl:2158/1357179.
^ Frazier, D. R.; S. K. Lynch; G. O. Carlisle (1981). "Synthesis and magnetic properties of bis[2-(4-isobutylphenyl)propionato]copper(II)". Journal of Inorganic and Nuclear Chemistry. 43 (11): 2747–2748. doi:10.1016/0022-1902(81)80610-0.
^ Abuhijleh AL (September 1994). "Mononuclear and binuclear copper(II) complexes of the antiinflammatory drug ibuprofen: synthesis, characterization, and catecholase-mimetic activity". J. Inorg. Biochem. 55 (4): 255–62. doi:10.1016/0162-0134(94)85010-0. PMID 7964714.
^ Sorenson JR (1989). "Copper complexes offer a physiological approach to treatment of chronic diseases". Prog Med Chem. Progress in Medicinal Chemistry. 26: 437–568. doi:10.1016/s0079-6468(08)70246-7. ISBN 9780444810380. PMID 2690187.
^ Gordijo CR, Barbosa CA, Da Costa Ferreira AM, Constantino VR, de Oliveira Silva D (May 2005). "Immobilization of ibuprofen and copper-ibuprofen drugs on layered double hydroxides". J Pharm Sci. 94 (5): 1135–48. Bibcode:2005JPhmS..94.1135G. doi:10.1002/jps.20336. PMID 15793807.
^ US patent 7462227, Anderson, Albert Gordon; Feaster, John; Patel, Damini; Scialdone, Mark, "Ibuprofen complexes as wood preservatives", issued 2007-07-26

[XRD-1] Lippi, Martina; Paoli, Paola; Conti, Luca; Giacomazzo, Gina Elena; MacEdi, Eleonora; Ceccarelli, Jacopo; Missina, Juliana Morais; Fagorzi, Camilla; Rossi, Patrizia (2024). "Ibuprofen: A multi-purpose active pharmaceutical ingredient as versatile ligand for zinc(II) and copper(II). Solid state and solution studies". Inorganica Chimica Acta. 566 122034. doi:10.1016/j.ica.2024.122034. hdl:2158/1357179.

[Frazier-2] Frazier, D. R.; S. K. Lynch; G. O. Carlisle (1981). "Synthesis and magnetic properties of bis[2-(4-isobutylphenyl)propionato]copper(II)". Journal of Inorganic and Nuclear Chemistry. 43 (11): 2747–2748. doi:10.1016/0022-1902(81)80610-0.

[Abu-3] Abuhijleh AL (September 1994). "Mononuclear and binuclear copper(II) complexes of the antiinflammatory drug ibuprofen: synthesis, characterization, and catecholase-mimetic activity". J. Inorg. Biochem. 55 (4): 255–62. doi:10.1016/0162-0134(94)85010-0. PMID 7964714.

[Sorenson-4] Sorenson JR (1989). "Copper complexes offer a physiological approach to treatment of chronic diseases". Prog Med Chem. Progress in Medicinal Chemistry. 26: 437–568. doi:10.1016/s0079-6468(08)70246-7. ISBN 9780444810380. PMID 2690187.

[Gordijo-5] Gordijo CR, Barbosa CA, Da Costa Ferreira AM, Constantino VR, de Oliveira Silva D (May 2005). "Immobilization of ibuprofen and copper-ibuprofen drugs on layered double hydroxides". J Pharm Sci. 94 (5): 1135–48. Bibcode:2005JPhmS..94.1135G. doi:10.1002/jps.20336. PMID 15793807.

[6] US patent 7462227, Anderson, Albert Gordon; Feaster, John; Patel, Damini; Scialdone, Mark, "Ibuprofen complexes as wood preservatives", issued 2007-07-26

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