Copper ibuprofenate

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Copper ibuprofenate
Copper(II) Ibuprofenate.jpg
Anhydrous
Copper(II) Ibuprofenate Hydrate.jpg
Monohydrate
Cu2(ibuprofenate)4.svg
R = (CH3)2CHCH2C6H4CH(CH3)-
Names
IUPAC name
bis[2-(4-isobutylphenyl)propionato]copper(II)
Identifiers
3D model (JSmol)
PubChem CID
  • 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
  • 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
C52H68Cu2O8
Molar mass 948.200 g·mol−1
AppearanceBlue Powder
Density 1.299 g/cm3 [1]
Slightly soluble
Solubility in isopropanolSlightly 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).
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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 2 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 .
  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. ↑ 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. ↑ USpatent 7462227,Anderson, Albert Gordon; Feaster, John; Patel, Damini; Scialdone, Mark,"Ibuprofen complexes as wood preservatives",issued 2007-07-26
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