Oxicam

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Piroxicam, the most popular drug of the oxicam class. Piroxicam.svg
Piroxicam, the most popular drug of the oxicam class.

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]

Contents

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] Piroxicam tautomers.svg

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.

Related Research Articles

<span class="mw-page-title-main">Analgesic</span> Any member of the group of drugs used to achieve analgesia, relief from pain

An analgesic drug, also called simply an analgesic, pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in some instances eliminate, sensation, although analgesia and anesthesia are neurophysiologically overlapping and thus various drugs have both analgesic and anesthetic effects.

<span class="mw-page-title-main">Nonsteroidal anti-inflammatory drug</span> Class of therapeutic drug for relieving pain and inflammation

Non-steroidal anti-inflammatory drugs (NSAID) are members of a therapeutic drug class which reduces pain, decreases inflammation, decreases fever, and prevents blood clots. Side effects depend on the specific drug, its dose and duration of use, but largely include an increased risk of gastrointestinal ulcers and bleeds, heart attack, and kidney disease.

<span class="mw-page-title-main">Ibuprofen</span> Medication used for treating pain, fever, and inflammation

Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used to relieve 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.

<span class="mw-page-title-main">Diclofenac</span> Nonsteroidal anti-inflammatory drug


Diclofenac, sold under the brand name Voltaren, among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammatory diseases such as gout. It is taken by mouth or rectally in a suppository, used by injection, or applied to the skin. Improvements in pain last for as much as eight hours. It is also available in combination with misoprostol in an effort to decrease stomach problems.

<span class="mw-page-title-main">Naproxen</span> Nonsteroidal anti-inflammatory drug (NSAID) used to treat pain

Naproxen, sold under the brand name Aleve 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 lasts for up to twelve hours.

<span class="mw-page-title-main">Rofecoxib</span> Nonsteroidal anti-inflammatory drug

Rofecoxib is a COX-2-selective nonsteroidal anti-inflammatory drug (NSAID). It was marketed by Merck & Co. to treat osteoarthritis, rheumatoid arthritis, juvenile rheumatoid arthritis, acute pain conditions, migraine, and dysmenorrhea. Rofecoxib was approved in the US by the US Food and Drug Administration (FDA) in May 1999, and was marketed under the brand names Vioxx, Ceoxx, and Ceeoxx. Rofecoxib was available by prescription in both tablets and as an oral suspension.

Anti-inflammatory or antiphlogistic is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as opposed to opioids, which affect the central nervous system to block pain signaling to the brain.

COX-2 inhibitors (coxibs) are a type of nonsteroidal anti-inflammatory drug (NSAID) that directly target cyclooxygenase-2, COX-2, an enzyme responsible for inflammation and pain. Targeting selectivity for COX-2 reduces the risk of peptic ulceration and is the main feature of celecoxib, rofecoxib, and other members of this drug class.

<span class="mw-page-title-main">Mefenamic acid</span> Chemical compound

Mefenamic acid is a member of the anthranilic acid derivatives class of nonsteroidal anti-inflammatory drugs (NSAIDs), and is used to treat mild to moderate pain.

<span class="mw-page-title-main">Oxaprozin</span> Chemical compound

Oxaprozin, also known as oxaprozinum, is a nonsteroidal anti-inflammatory drug (NSAID), used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis. Chemically, it is a propionic acid derivative. Safety and efficacy has been established in children over 6 years with juvenile rheumatoid arthritis only, and there is an increased risk of adverse reactions in the elderly population.

<span class="mw-page-title-main">Piroxicam</span> Chemical compound

Piroxicam is a nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class used to relieve the symptoms of painful inflammatory conditions like arthritis. Piroxicam works by preventing the production of endogenous prostaglandins which are involved in the mediation of pain, stiffness, tenderness and swelling. The medicine is available as capsules, tablets and as a prescription-free gel 0.5%. It is also available in a betadex formulation, which allows a more rapid absorption of piroxicam from the digestive tract. Piroxicam is one of the few NSAIDs that can be given parenteral routes.

<span class="mw-page-title-main">Meloxicam</span> Nonsteroidal anti-inflammatory drug (NSAID)

Meloxicam, sold under the brand name Mobic among others, is a nonsteroidal anti-inflammatory medication (NSAID) used to treat pain and inflammation in rheumatic diseases and osteoarthritis. It is used by mouth or by injection into a vein. It is recommended that it be used for as short a period as possible and at a low dose.

<span class="mw-page-title-main">Carprofen</span> Non-steroidal anti-inflammatory drug

Carprofen is a non-steroidal anti-inflammatory drug (NSAID) of the carbazole and propionic acid class that was previously for use in humans and animals, but is now only available to veterinarians for prescribing as a supportive treatment for various conditions in only animals. Carprofen reduces inflammation by inhibition of COX-1 and COX-2; its specificity for COX-2 varies from species to species. Marketed under many brand names worldwide, carprofen provides day-to-day treatment for pain and inflammation from various kinds of joint pain, as well as post-operative pain.

<span class="mw-page-title-main">Meclofenamic acid</span> Chemical compound

Meclofenamic acid is a drug used for joint, muscular pain, arthritis and dysmenorrhea. It is a member of the anthranilic acid derivatives class of nonsteroidal anti-inflammatory drugs (NSAIDs) and was approved by the US FDA in 1980. Like other members of the class, it is a cyclooxygenase (COX) inhibitor, preventing the formation of prostaglandins.

<span class="mw-page-title-main">Flunoxaprofen</span> Chemical compound

Flunoxaprofen, also known as Priaxim, is a chiral nonsteroidal anti-inflammatory drug (NSAID). It is closely related to naproxen, which is also an NSAID. Flunoxaprofen has been shown to significantly improve the symptoms of osteoarthritis and rheumatoid arthritis. The clinical use of flunoxaprofen has ceased due to concerns of potential hepatotoxicity.

<span class="mw-page-title-main">Lornoxicam</span> Chemical compound

Lornoxicam, also known as chlortenoxicam, is a nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class with analgesic, anti-inflammatory and antipyretic properties. It is available in oral and parenteral formulations.

<span class="mw-page-title-main">Tenoxicam</span> Chemical compound

Tenoxicam, sold under the brand name Mobiflex among others, is a nonsteroidal anti-inflammatory drug (NSAID). It is used to relieve inflammation, swelling, stiffness, and pain associated with rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, tendinitis, bursitis, and periarthritis of the shoulders or hips.

COX-inhibiting nitric oxide donators (CINODs), also known as NO-NSAIDs, are a new class of nonsteroidal anti-inflammatory drug (NSAID) developed with the intention of providing greater safety than existing NSAIDs.

Cyclooxygenases are enzymes that take part in a complex biosynthetic cascade that results in the conversion of polyunsaturated fatty acids to prostaglandins and thromboxane(s). Their main role is to catalyze the transformation of arachidonic acid into the intermediate prostaglandin H2, which is the precursor of a variety of prostanoids with diverse and potent biological actions. Cyclooxygenases have two main isoforms that are called COX-1 and COX-2. COX-1 is responsible for the synthesis of prostaglandin and thromboxane in many types of cells, including the gastro-intestinal tract and blood platelets. COX-2 plays a major role in prostaglandin biosynthesis in inflammatory cells and in the central nervous system. Prostaglandin synthesis in these sites is a key factor in the development of inflammation and hyperalgesia. COX-2 inhibitors have analgesic and anti-inflammatory activity by blocking the transformation of arachidonic acid into prostaglandin H2 selectively.

Prostaglandin inhibitors are drugs that inhibit the synthesis of prostaglandin in human body. There are various types of prostaglandins responsible for different physiological reactions such as maintaining the blood flow in stomach and kidney, regulating the contraction of involuntary muscles and blood vessels, and act as a mediator of inflammation and pain. Cyclooxygenase (COX) and Phospholipase A2 are the major enzymes involved in prostaglandin production, and they are the drug targets for prostaglandin inhibitors. There are mainly 2 classes of prostaglandin inhibitors, namely non- steroidal anti- inflammatory drugs (NSAIDs) and glucocorticoids. In the following sections, the medical uses, side effects, contraindications, toxicity and the pharmacology of these prostaglandin inhibitors will be discussed.

References

  1. 1 2 3 4 5 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.
  2. 1 2 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 . England, UK: Royal Society of Chemistry. 5 (40): 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. Elsevier. 59 (6): 1213–22. Bibcode:2003AcSpA..59.1213B. doi:10.1016/S1386-1425(02)00300-1. PMID   12659890.