From Wikipedia, the free encyclopedia
Drug class
Piroxicam , the most popular drug of the oxicam class.
[1]
Oxicam is a class of
non-steroidal anti-inflammatory drugs (NSAIDs),
[2] meaning that they have
anti-inflammatory ,
analgesic , and antipyretic therapeutic effects. Oxicams bind closely to
plasma proteins .
[1] Most oxicams are unselective inhibitors of the
cyclooxygenase (COX) enzymes. The exception is
meloxicam with a slight (10:1) preference for
COX-2 , which, however, is only clinically relevant at low doses.
[3]
The most popular drug of the oxicam class is
piroxicam .
[1] Other examples include:
ampiroxicam ,
droxicam ,
pivoxicam ,
tenoxicam ,
lornoxicam ,
[1] and
meloxicam .
Isoxicam has been suspended as a result of fatal skin reactions.
[1]
Chemistry
The physico-chemical characteristics of these molecules vary greatly depending upon the environment.
[4]
In contrast to most other NSAIDs, oxicams are not
carboxylic acids . They are
tautomeric , and can exist as a number of tautomers (
keto-enol tautomerism ), here exemplified by piroxicam:
[2]
Side effects
The oxicams are associated with drug-related
erythema multiforme (EM),
Stevens–Johnson syndrome , and
toxic epidermal necrolysis (TEN). This association is one of the reasons oxicams are not regularly prescribed.
References
^
a
b
c
d
e Olkkola 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 .
^
a
b Ivanova 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 .
^ 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 .
^ 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 .
Receptor (
ligands )
DP (D2 ) Tooltip Prostaglandin D2 receptor
DP1 Tooltip Prostaglandin D2 receptor 1
DP2 Tooltip Prostaglandin D2 receptor 2
EP (E2 ) Tooltip Prostaglandin E2 receptor
EP1 Tooltip Prostaglandin EP1 receptor
EP2 Tooltip Prostaglandin EP2 receptor
EP3 Tooltip Prostaglandin EP3 receptor
EP4 Tooltip Prostaglandin EP4 receptor Unsorted
FP (F2α ) Tooltip Prostaglandin F receptor
IP (I2 ) Tooltip Prostacyclin receptor
TP (TXA2 ) Tooltip Thromboxane receptor Unsorted
Enzyme (
inhibitors )
COX (
PTGS )
PGD2 S Tooltip Prostaglandin D synthase
PGES Tooltip Prostaglandin E synthase
PGFS Tooltip Prostaglandin F synthase
PGI2 S Tooltip Prostacyclin synthase
TXAS Tooltip Thromboxane A synthase
Others