Dexketoprofen

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Dexketoprofen
Dexketoprofen.png
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Clinical data
AHFS/Drugs.com International Drug Names
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Identifiers
  • (2S)-2-[3-(benzoyl)phenyl]propanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.118.639 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H14O3
Molar mass 254.285 g·mol−1
3D model (JSmol)
  • C[C@@H](c1cccc(c1)C(=O)c2ccccc2)C(=O)O
  • InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)/t11-/m0/s1 X mark.svgN
  • Key:DKYWVDODHFEZIM-NSHDSACASA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Dexketoprofen is a nonsteroidal anti-inflammatory drug (NSAID). It is manufactured by Menarini, under the tradename Keral. It is available in the UK, as dexketoprofen trometamol, as a prescription-only drug and in Latin America as Enantyum, produced by Menarini. Also, in Italy and Spain it is available as an over-the-counter drug (OTC) under the trade name Enandol or Enantyum. In Hungary it is available from a pharmacy as "Ketodex". In Turkey, it is an over the counter medicine under the name "Arveles". In Latvia, Lithuania and Estonia it is available as an OTC under the tradename Dolmen. [1] In Mexico it is available in tablet form as "Stadium" made by Menarini. It is the dextrorotatory stereoisomer of ketoprofen. [2]

Contents

Chemistry

Dexketoprofen is the (S)-enantiomer of ketoprofen. Technically it is a chiral switch of (±)-ketoprofen. The switch was done for a faster onset of action, a better therapeutic value. [3] Dexketoprofen consists of a propionic acid moiety connected to a benzophenone molecule by its second carbon.

Medical uses

Short-term treatment of mild to moderate pain, including dysmenorrhoea. It is also used for migraines and knee pain.

Side effects

It may cause dizziness, and patients should not, therefore, drive or operate heavy machinery or vehicles until they are familiar with how dexketoprofen affects them. Concomitant use of alcohol and other sedatives may potentiate this effect. In a small subset of individuals the dizziness may be intolerable and require transition to an alternative treatment.

Pharmacology

Dexketoprofen belongs to a class of medicines called NSAIDs. It works by blocking the action of a substance in the body called cyclo-oxygenase, which is involved in the production of chemicals in the body called prostaglandins. Prostaglandins are produced in response to injury or certain diseases and would otherwise go on to cause swelling, inflammation and pain. By blocking cyclo-oxygenase, dexketoprofen prevents the production of prostaglandins and therefore reduces inflammation and pain. Along with peripheral analgesic action, it possesses central analgesic action.

See also

Related Research Articles

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An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. 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">Ketoprofen</span> NSAID analgesic medication

Ketoprofen is one of the propionic acid class of nonsteroidal anti-inflammatory drugs (NSAID) with analgesic and antipyretic effects. It acts by inhibiting the body's production of prostaglandin.

<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.

An antipyretic is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which results in a reduction in fever.

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

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<span class="mw-page-title-main">Cyclooxygenase</span> Class of enzymes

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

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Cyclooxygenase-3 (COX-3) is an enzyme that is encoded by the PTGS1 (COX1) gene, but is not functional in humans. COX-3 is the third and most recently discovered cyclooxygenase (COX3050) isozyme, while the first two to be discovered were COX-1 and COX-2. The COX-3 isozyme is encoded by the same gene as COX-1, with the difference that COX-3 retains an intron that is not retained in COX-1.

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

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

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

Carprofen is a nonsteroidal 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 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 is used as a treatment for inflammation and pain, including joint pain and postoperative pain.

<span class="mw-page-title-main">Metamizole</span> Medication

Metamizole or dipyrone is a painkiller, spasm reliever, and fever reliever drug. It is most commonly given by mouth or by intravenous infusion. It belongs to the ampyrone sulfonate family of medicines and was patented in 1922. Metamizole is marketed under various trade names. It was first used medically in Germany under the brand name "Novalgin", and then became widely known in Slavic nations and India under the name "Analgin".

<span class="mw-page-title-main">Fenoprofen</span> NSAID analgesic and anti-inflammatory drug

Fenoprofen, sold under the brand name Nalfon among others, is a nonsteroidal anti-inflammatory drug (NSAID). Fenoprofen calcium is used for symptomatic relief for rheumatoid arthritis, osteoarthritis, and mild to moderate pain. It has also been used to treat postoperative pain. It is available as a generic medication.

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

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.

Naproxcinod (nitronaproxen) is a nonsteroidal anti-inflammatory drug (NSAID) developed by the French pharmaceutical company NicOx. It is a derivative of naproxen with a nitroxybutyl ester to allow it to also act as a nitric oxide (NO) donor. This second mechanism of action makes naproxcinod the first in a new class of drugs, the cyclooxygenase inhibiting nitric oxide donators (CINODs), that are hoped to produce similar analgesic efficacy to traditional NSAIDs, but with less gastrointestinal and cardiovascular side effects.

<span class="mw-page-title-main">Antiarthritics</span> Drug class

An antiarthritic is any drug used to relieve or prevent arthritic symptoms, such as joint pain or joint stiffness. Depending on the antiarthritic drug class, it is used for managing pain, reducing inflammation or acting as an immunosuppressant. These drugs are typically given orally, topically or through administration by injection. The choice of antiarthritic medication is often determined by the nature of arthritis, the severity of symptoms as well as other factors, such as the tolerability of side effects.

References

  1. ↑ "Medicinal products authorised in Estonia". State Agency of Medicine. 22 May 2014. Archived from the original on 22 January 2016. Retrieved 23 May 2014.
  2. ↑ Chandrasekharan NV (2007). "Dexketoprofen". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. Elsevier Inc. pp. 1–4. doi:10.1016/B978-008055232-3.61574-0. ISBN   978-0-08-055232-3.
  3. ↑ Tucker GT (March 2000). "Chiral switches". Lancet. 355 (9209): 1085–7. doi:10.1016/s0140-6736(00)02047-x. PMID   10744105. S2CID   30715334.
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