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Oxicam

From Wikipedia, the free encyclopedia
Drug class
Piroxicam, the most popular drug of the oxicam class.[1]

Oxicam is a class ofnon-steroidal anti-inflammatory drugs (NSAIDs),[2] meaning that they haveanti-inflammatory,analgesic, and antipyretic therapeutic effects. Oxicams bind closely toplasma proteins.[1] Most oxicams are unselective inhibitors of thecyclooxygenase (COX) enzymes. The exception ismeloxicam with a slight (10:1) preference forCOX-2, which, however, is only clinically relevant at low doses.[3]

The most popular drug of the oxicam class ispiroxicam.[1] Other examples include:ampiroxicam,droxicam,pivoxicam,tenoxicam,lornoxicam,[1] andmeloxicam.

Isoxicam has been suspended as a result of fatal skin reactions.[1]

Chemistry

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The physico-chemical characteristics of these molecules vary greatly depending upon the environment.[4]

In contrast to most other NSAIDs, oxicams are notcarboxylic acids. They aretautomeric, and can exist as a number of tautomers (keto-enol tautomerism), here exemplified by piroxicam:[2]

Side effects

[edit]
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The oxicams are associated with drug-relatederythema multiforme (EM),Stevens–Johnson syndrome, andtoxic epidermal necrolysis (TEN). This association is one of the reasons oxicams are not regularly prescribed.

References

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  1. ^abcdeOlkkola KT, Brunetto AV, Mattila MJ (February 1994). "Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents".Clinical Pharmacokinetics.26 (2):107–20.doi:10.2165/00003088-199426020-00004.PMID 8162655.S2CID 13300943.
  2. ^abIvanova D, Deneva V, Nedeltcheva D, Kamounah FS, Gergov G, Hansen PE, Kawauchi S, Antonov L (March 2015)."Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study".RSC Advances.5 (40). England, UK:Royal Society of Chemistry:31852–31860.Bibcode:2015RSCAd...531852I.doi:10.1039/c5ra03653d.
  3. ^Mutschler, Ernst; Gerd Geisslinger; Heyo K. Kroemer; Monika Schäfer-Korting (2001).Mutschler Arzneimittelwirkungen: Lehrbuch der Pharmakologie und Toxikologie; mit einführenden Kapiteln in die Anatomie, Physiologie und Pathophysiologie [Mutster medicine effects: Textbook of pharmacology and toxicology; with introductory chapters in anatomy, physiology and pathophysiology] (in German) (8 ed.).Stuttgart, Germany:Wissenschaftliche Verlagsgesellschaft. p. 233.ISBN 3-8047-1763-2.OCLC 48723029.OL 12928661M.
  4. ^Banerjee R, Chakraborty H, Sarkar M (April 2003). "Photophysical studies of oxicam group of NSAIDs: piroxicam, meloxicam and tenoxicam".Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy.59 (6).Elsevier:1213–22.Bibcode:2003AcSpA..59.1213B.doi:10.1016/S1386-1425(02)00300-1.PMID 12659890.
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
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Enzyme
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COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
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TXASTooltip Thromboxane A synthase
Others


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