Oxyphenbutazone

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

Oxyphenbutazone
Clinical data
Trade namesTandearil, Tanderil
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
  • AU: Withdrawn
  • UK: Withdrawn
  • US: Withdrawn
Identifiers
IUPAC name
  • (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 InfoCard100.004.489
Chemical and physical data
FormulaC19H20N2O3
Molar mass324.380 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • O=C2N(c1ccc(O)cc1)N(C(=O)C2CCCC)c3ccccc3.O
InChI
  • 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 Y
  • Key:CNDQSXOVEQXJOE-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of Stevens–Johnson syndrome.[3][4]

The word "oxyphenbutazone" is, theoretically, the highest-scoring word under American rules for Scrabble, with a maximum possible score of 1,778 points.[5]

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 JM (12 April 2017). "10 Words That Will Win You Any Game of Scrabble". Mental Floss.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.