Copper ibuprofenate

Anhydrous

Monohydrate

R = (CH3)2CHCH2C6H4CH(CH3)-

Names
IUPAC name

bis[2-(4-isobutylphenyl)propionato]copper(II)

Identifiers

CAS Number

* 66840-44-6 Y

3D model (JSmol)

* Interactive image

PubChem CID

* 23978

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[1]

Solubility in water

| Slightly soluble
Solubility in isopropanol  | Slightly soluble
Related compounds

Related compounds

| Copper aspirinate

Ibuprofen

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Copper ibuprofenate is a coordination complex consisting of copper(II) and the conjugate base of ibuprofen. The compound is prepared by the reaction of sodium ibuprofenate with copper(II) sulfate.[2][3]

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]

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

1. ↑ 1.0 1.1 Lippi, Martina; Paoli, Paola; Conti, Luca; Giacomazzo, Gina Elena; MacEdi, Eleonora; Ceccarelli, Jacopo; Missina, Juliana Morais; Fagorzi, Camilla et al. (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. doi:10.1016/j.ica.2024.122034.
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.
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.
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.
5. ↑ "Immobilization of ibuprofen and copper-ibuprofen drugs on layered double hydroxides". J Pharm Sci 94 (5): 1135–48. May 2005. doi:10.1002/jps.20336. PMID 15793807. Bibcode: 2005JPhmS..94.1135G.
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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*[CID]: Compound ID