Oxyphenbutazone

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Oxyphenbutazone
Oxyphenbutazone.svg
Clinical data
Trade names Tandearil, Tanderil
AHFS/Drugs.com International Drug Names
ATC code
Legal status
Legal status
  • AU:Withdrawn
  • UK:Withdrawn
  • US:Withdrawn
Identifiers
  • (RS)-4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.004.489 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H20N2O3
Molar mass 324.380 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • O=C2N(c1ccc(O)cc1)N(C(=O)C2CCCC)c3ccccc3.O
  • InChI=1S/C19H20N2O3.H2O/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15;/h4-8,10-13,17,22H,2-3,9H2,1H3;1H2 Yes check.svgY
  • Key:CNDQSXOVEQXJOE-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Oxyphenbutazone is a nonsteroidal anti-inflammatory drug (NSAID). [1] It is a metabolite of phenylbutazone. [2]

It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of Stevens–Johnson syndrome. [3] [4]

In Scrabble , the word "oxyphenbutazone" is the present highest scoring word resulting in 1,780 points based on the NASPA word list of 2006. [5]

Related Research Articles

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<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">Cyclooxygenase</span> Class of enzymes

Cyclooxygenase (COX), officially known as prostaglandin-endoperoxide synthase (PTGS), is an enzyme that is responsible for biosynthesis 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.

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

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<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, and 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. Naproxen is also available in salt form, naproxen sodium, which has better solubility when taken orally.

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

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<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, in some countries, 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">Flunixin</span> NSAID analgesic veterinary drug

Flunixin is a nonsteroidal anti-inflammatory drug (NSAID), analgesic, and antipyretic used in horses, cattle and pigs. It is often formulated as the meglumine salt. In the United States, it is regulated by the U.S. Food and Drug Administration (FDA), and may only be lawfully distributed by order of a licensed veterinarian. There are many trade names for the product.

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

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

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<span class="mw-page-title-main">Tepoxalin</span> NSAID anti-inflammatory veterinary drug

Tepoxalin, sold under the brand name Zubrin among others, is a non-steroidal anti-flammatory drug (NSAIDs) generally used in veterinary medicine to reduce swelling in animals with osteoarthritis. In rare circumstances, tepoxalin can also be used in human pharmacology to relieve pain caused by musculoskeletal conditions such as arthritis and hip dysplasia.

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

Amtolmetin guacil is a non-steroidal anti-inflammatory drug (NSAID). It is a prodrug of tolmetin sodium.

<span class="mw-page-title-main">Tolmetin</span> NSAID analgesic medication

Tolmetin is a nonsteroidal anti-inflammatory drug (NSAID) of the heterocyclic acetic acid derivative class.

<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.

Clofezone is a drug that was used to treat joint and muscular pain, but is not marketed any more. It is a combination of clofexamide, an antidepressant, and phenylbutazone, a nonsteroidal anti-inflammatory drug (NSAID).

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

Salsalate is a medication that belongs to the salicylate and nonsteroidal anti-inflammatory drug (NSAID) classes.

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

Clofexamide is an antidepressant that was a component of the drug combination clofezone, the other being the nonsteroidal anti-inflammatory drug (NSAID) phenylbutazone. Clofezone was used to treat joint and muscular pain, but is not marketed any more.

NSAIDhypersensitivity reactions encompass a broad range of allergic or allergic-like symptoms that occur within minutes to hours after ingesting aspirin or other NSAID nonsteroidal anti-inflammatory drugs. Hypersensitivity drug reactions differ from drug toxicity reactions in that drug toxicity reactions result from the pharmacological action of a drug, are dose-related, and can occur in any treated individual. Hypersensitivity reactions are idiosyncratic reactions to a drug. Although the term NSAID was introduced to signal a comparatively low risk of adverse effects, NSAIDs do evoke a broad range of hypersensitivity syndromes. These syndromes have recently been classified by the European Academy of Allergy and Clinical Immunology Task Force on NSAIDs Hypersensitivity.

<span class="mw-page-title-main">Isoxicam</span> Withdrawn NSAID analgesic drug

Isoxicam is a nonsteroidal anti-inflammatory drug (NSAID) that was taken or applied to reduce inflammation and as an analgesic reducing pain in certain conditions. The drug was introduced in 1983 by the Warner-Lambert Company. Isoxicam is a chemical analog of piroxicam (Feldene) which has a pyridine ring in lieu of an isoxazole ring. In 1985 isoxicam was withdrawn from the French market, due to adverse effects, namely toxic epidermal necrolysis resulting in death. Although these serious side effects were observed only in France, the drug was withdrawn worldwide.

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. Singh N, Jabeen T, Somvanshi RK, Sharma S, Dey S, Singh TP (November 2004). "Phospholipase A2 as a target protein for nonsteroidal anti-inflammatory drugs (NSAIDS): crystal structure of the complex formed between phospholipase A2 and oxyphenbutazone at 1.6 A resolution". Biochemistry. 43 (46): 14577–83. doi:10.1021/bi0483561. PMID   15544328.
  2. Matthews NS, Peck KE, Taylor TS, Mealey KL (May 2001). "Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys". American Journal of Veterinary Research. 62 (5): 673–5. doi: 10.2460/ajvr.2001.62.673 . PMID   11341383.
  3. Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E (January 2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Therapeutic Innovation & Regulatory Science. 35 (1): 293–317. doi:10.1177/009286150103500134. S2CID   73036562.
  4. Biron P (May 1986). "Withdrawal of oxyphenbutazone: what about phenylbutazone?". CMAJ. 134 (10): 1119–20. PMC   1491052 . PMID   3697857.
  5. Wood D (22 May 2008). "Record for the Highest Scoring Scrabble Move". Scrabulizer. Archived from the original on 11 May 2023.