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Oxyphenbutazone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Oxyphenbutazone
Clinical data
Trade namesTandearil, Tanderil
AHFS/Drugs.comInternational Drug Names
ATC code
Legal status
Legal status
Identifiers
  • (RS)-4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.004.489Edit this at Wikidata
Chemical and physical data
FormulaC19H20N2O3
Molar mass324.380 g·mol−1
3D model (JSmol)
ChiralityRacemic 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 checkY
  • Key:CNDQSXOVEQXJOE-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Oxyphenbutazone is anonsteroidal anti-inflammatory drug (NSAID).[1] It is ametabolite ofphenylbutazone.[2]

It was withdrawn from markets worldwide in the mid-1980s due to bone marrow suppression and the risk ofStevens–Johnson syndrome.[3][4]

InScrabble, the word "oxyphenbutazone" is the highest-scoring word possible resulting in 1,780 points based on theNASPA word list of 2006.[5] However, according toMental Floss, there is no documentation that the word "oxyphenbutazone" has ever been successfully played on aScrabble board, and it "probably never will be".[6]

References

[edit]
  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. Retrieved12 March 2025.
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
Topical products forjoint andmuscular pain (M02)
Anti-inflammatory
preparations,
non-steroids
Pyrazolidines
Acetic acid
derivatives
Other
Capsaicin derivatives
Other


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