Oxyphenbutazone

Last updated
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  • AU:Withdrawn
  • UK:Withdrawn
  • US:Withdrawn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It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of Stevens–Johnson syndrome.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 highest-scoring word possible resulting in 1,780 points based on the NASPA word list of 2006. [5] However, according to Mental Floss , there is no documentation that the word "oxyphenbutazone" has ever been successfully played on a Scrabble board, and it "probably never will be". [6]

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.
  6. ↑ Wood, Jennifer M. "11 Words That Will Win You Any Game of Scrabble". Mental Floss. Retrieved 12 March 2025.


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