Copper ibuprofenate

Last updated
Copper(II) Ibuprofenate.jpg
IBPCOP.jpg
Names
IUPAC name
bis[2-(4-isobutylphenyl)propionato]copper(II)
Identifiers
  • 66840-44-6 Yes check.svgY
3D model (JSmol)
  • InChI=1S/4C13H17O2.2Cu/c4*1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15;;/h4*4-7,9-10H,8H2,1-3H3;;/q4*-3;2*+6
    Key: HEFOJHHJEKPEDO-UHFFFAOYSA-N
  • c0cc(CC(C)C)ccc0C(C)[c-](O[Cu+2]123)O[Cu+2](O[c-](O1)C(C)c0ccc(CC(C)C)cc0)(O[c-](O2)C(C)c0ccc(CC(C)C)cc0)O[c-](O3)C(C)c0ccc(CC(C)C)cc0
Properties
C52H68Cu2O8
Molar mass 948.200 g·mol−1
AppearanceGreen powder
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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Infobox references

Copper ibuprofenate is a chemical complex consisting of copper(II) and the chelate form of the anti-inflammatory drug ibuprofen. [1] [2] The compound is prepared by the reaction of sodium ibuprofenate with copper(II) sulfate.

It has been suggested that copper complexes of anti-inflammatory drugs are more active than the parent drug [3] and produce fewer gastrointestinal side-effects. [4] In 2008, a United States patent was issued for the utilization of ibuprofenate complexes (including copper ibuprofenate) as a wood preservative. [5]

Related Research Articles

Nonsteroidal anti-inflammatory drugs (NSAIDs) are members of a drug class that reduces pain, decreases fever, prevents blood clots, and in higher doses, decreases inflammation. Side effects depend on the specific drug but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.

Ibuprofen Medication used for treating pain, fever, and inflammation

Ibuprofen is a medication in the nonsteroidal anti-inflammatory drug (NSAID) class that is used for treating pain, fever, and inflammation. This includes painful menstrual periods, migraines, and rheumatoid arthritis. It may also be used to close a patent ductus arteriosus in a premature baby. It can be used by mouth or intravenously. It typically begins working within an hour.

Cyclooxygenase

Cyclooxygenase (COX), officially known as prostaglandin-endoperoxide synthase (PTGS), is an enzyme that is responsible for formation of prostanoids, including thromboxane and prostaglandins such as prostacyclin, from arachidonic acid. A member of the animal-type heme peroxidase family, it is also known as prostaglandin G/H synthase. The specific reaction catalyzed is the conversion from arachidonic acid to Prostaglandin H2, via a short-living Prostaglandin G2 intermediate.

Naproxen Nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout, and fever

Naproxen, sold under the brand name Aleve or Apronax among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and last for up to twelve hours.

Celecoxib Nonsteroidal anti-inflammatory drug

Celecoxib, sold under the brand name Celebrex among others, is a COX-2 inhibitor and nonsteroidal anti-inflammatory drug (NSAID). It is used to treat the pain and inflammation in osteoarthritis, acute pain in adults, rheumatoid arthritis, ankylosing spondylitis, painful menstruation, and juvenile rheumatoid arthritis. It may also be used to decrease the risk of colorectal adenomas in people with familial adenomatous polyposis. It is taken by mouth. Benefits are typically seen within an hour.

Dendrimer

Dendrimers are highly ordered, branched polymeric molecules. Synonymous terms for dendrimer include arborols and cascade molecules. Typically, dendrimers are symmetric about the core, and often adopt a spherical three-dimensional morphology. The word dendron is also encountered frequently. A dendron usually contains a single chemically addressable group called the focal point or core. The difference between dendrons and dendrimers is illustrated in the top figure, but the terms are typically encountered interchangeably.

Benzimidazole Chemical compound

Benzimidazole is a heterocyclic aromatic organic compound. This bicyclic compound consists of the fusion of benzene and imidazole. It is a colorless solid.

Oleocanthal Chemical compound

Oleocanthal is a phenylethanoid, or a type of natural phenolic compound found in extra-virgin olive oil. It appears to be responsible for the burning sensation that occurs in the back of the throat when consuming such oil. Oleocanthal is a tyrosol ester and its chemical structure is related to oleuropein, also found in olive oil.

CCL3

Chemokine ligand 3 (CCL3) also known as macrophage inflammatory protein 1-alpha (MIP-1-alpha) is a protein that in humans is encoded by the CCL gene.

Dexibuprofen

Dexibuprofen is a nonsteroidal anti-inflammatory drug (NSAID).

Alpha-methylacyl-CoA racemase

Alpha-methylacyl-CoA racemase (AMACR) is an enzyme that in humans is encoded by the AMACR gene. AMACR catalyzes the following chemical reaction:

Gallium maltolate Chemical compound

Gallium maltolate is a coordination complex consisting of a trivalent gallium cation coordinated to three maltolate ligands. The compound is a potential therapeutic agent for cancer, infectious disease, and inflammatory disease. A cosmetic skin cream containing gallium maltolate is marketed under the name Gallixa. It is a colorless solid with significant solubility in both water and lipids.

Tebanicline Chemical compound

Tebanicline is a potent synthetic nicotinic (non-opioid) analgesic drug developed by Abbott. It was developed as a less toxic analog of the potent poison dart frog-derived compound epibatidine, which is about 200 times stronger than morphine as an analgesic, but produces extremely dangerous toxic side effects. Like epibatidine, tebanicline showed potent analgesic activity against neuropathic pain in both animal and human trials, but with far less toxicity than its parent compound. It acts as a partial agonist at neuronal nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes.

Arylcyclohexylamine

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

Hinokitiol Chemical compound

Hinokitiol (β-thujaplicin) is a natural monoterpenoid found in the wood of trees in the family Cupressaceae. It is a tropolone derivative and one of the thujaplicins. Hinokitiol is used in oral and skin care products, and is a food additive used in Japan.

Copper peptide GHK-Cu Chemical compound

Copper peptide GHK-Cu is a naturally occurring copper complex of the tripeptide glycyl-L-histidyl-L-lysine. The tripeptide has strong affinity for copper(II) and was first isolated from human plasma. It can be found also in saliva and urine.

Immunomodulatory imide drug class of immunomodulatory drugs

Immunomodulatory imide drugs (IMiDs) are a class of immunomodulatory drugs containing an imide group. The IMiD class includes thalidomide and its analogues (lenalidomide, pomalidomide, and iberdomide. These drugs may also be referred to as 'Cereblon modulators'. Cereblon is the protein targeted by this class of drugs.

Pregnenolone succinate

Pregnenolone succinate is a synthetic pregnane steroid and an ester of pregnenolone which is described as a glucocorticoid and anti-inflammatory drug and has been patented and marketed as a topical medication in the form of a cream for the treatment of allergic, pruritic, and inflammatory dermatitis. It has also been described as a non-hormonal sterol, having neurosteroid activity, and forming a progesterone analogue via dehydrogenation.

Embelin Chemical compound

Embelin (2,5-dihydroxy-3-undecyl-1,4-benzoquinone) is a naturally occurring para-benzoquinone isolated from dried berries of Embelia ribes plants. Embelin has a wide spectrum of biological activities, including antioxidant, antitumor, anti-inflammatory, analgesic, anthelmintic, antifertility and antimicrobial. Several studies have reported antidiabetic activity of embelin Embelin treatment significantly decreased paraquat‐induced lung injury through suppressing oxidative stress, inflammatory cascade, and MAPK/NF‐κB signaling pathway in paraquat‐intoxicated rats Embelin and embelin derivatives selectively inhibits 5-LOX and microsomal prostaglandin E2 synthase-1

The word "chiral switch" was introduced by Agranat and Caner in 1999. Chiral switches are chiral drugs that are already approved as racemates but that have been re-developed as single enantiomers. The term chiral switching has been coined to describe the development of single enantiomers from racemate drugs. For example, levofloxacin is a chiral switch of racemic ofloxacin. The essential principle of a chiral switch is that there is a change in the status of chirality. In general, the term chiral switch is preferred over racemic switch because the switch is usually happening from a racemic drug to the corresponding single enantiomer(s). It is important to understand that chiral switches are treated as a selection invention. A selection invention is an invention that selects a group of new members from a previously known class on the basis of superior properties. To express the pharmacological activities of each of the chiral twins of a racemic drug two technical terms have been coined eutomer and distomer. The member of the chiral twin that has greater physiological activity is referred to as the eutomer and the other one with lesser activity is referred to as distomer. The eutomer/distomer ratio is called the eudisimic ratio and reflects the degree of enantioselectivity of the biological activity.

References

  1. 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.
  2. 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.
  3. 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.
  4. 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. doi:10.1002/jps.20336. PMID   15793807.
  5. USpatent 7462227,Anderson, Albert Gordon; Feaster, John; Patel, Damini; Scialdone, Mark,"Ibuprofen complexes as wood preservatives",issued 2007-07-26

Further reading