Chemistry:Oxyphenbutazone

From HandWiki
Short description: Chemical compound
Oxyphenbutazone
Oxyphenbutazone.svg
Clinical data
Trade namesTandearil, Tanderil
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
  • AU: Withdrawn
  • UK: Withdrawn
  • US: Withdrawn
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H20N2O3
Molar mass324.380 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
 ☒N☑Y (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It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of Stevens–Johnson syndrome.[3][4]

Trivia

The word "oxyphenbutazone" is theoretically the highest-scoring Scrabble move known with 1,780 points, but playing the word would require extremely unlikely circumstances. (according to the TWL06 dictionary) [5]

References

  1. "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. November 2004. doi:10.1021/bi0483561. PMID 15544328. 
  2. "Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys". American Journal of Veterinary Research 62 (5): 673–5. May 2001. doi:10.2460/ajvr.2001.62.673. PMID 11341383. 
  3. "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. January 2001. doi:10.1177/009286150103500134. 
  4. "Withdrawal of oxyphenbutazone: what about phenylbutazone?". CMAJ 134 (10): 1119–20. May 1986. PMID 3697857. 
  5. Wood, Dave (22 May 2008). "Record for the Highest Scoring Scrabble Move". Scrabulizer. https://www.scrabulizer.com/blog/post/3#blog_post_break.