Oxyphenbutazone Explained
| Verifiedfields: | changed |
| Verifiedrevid: | 477171011 |
| Iupac Name: | (RS)-4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione |
| Width: | 250px |
| Chirality: | Racemic mixture |
| Tradename: | Tandearil, Tanderil |
| Legal Us Comment: | Withdrawn |
| Legal Uk: | Withdrawn |
| Legal Au: | Withdrawn |
| Cas Number: | 129-20-4 |
| Atc Prefix: | M01 |
| Atc Suffix: | AA03 |
| Pubchem: | 104811 |
| Drugbank: | DB03585 |
| Chemspiderid: | 94610 |
| Unii: | A7D84513GV |
| Kegg: | D08324 |
| Chebi: | 76258 |
| Chembl: | 1228 |
| C: | 19 |
| H: | 20 |
| N: | 2 |
| O: | 3 |
| Smiles: | O=C2N(c1ccc(O)cc1)N(C(=O)C2CCCC)c3ccccc3.O |
| Stdinchi: | 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 |
| Stdinchikey: | CNDQSXOVEQXJOE-UHFFFAOYSA-N |
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It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of Stevens–Johnson syndrome.[3] [4]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]
Notes and References
- Singh N, Jabeen T, Somvanshi RK, Sharma S, Dey S, Singh TP . 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 . 15544328 . 10.1021/bi0483561 .
- Matthews NS, Peck KE, Taylor TS, Mealey KL . Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys . American Journal of Veterinary Research . 62 . 5 . 673–5 . May 2001 . 11341383 . 10.2460/ajvr.2001.62.673 . free .
- Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E . Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999 . Therapeutic Innovation & Regulatory Science . January 2001 . 35 . 1 . 293–317 . 10.1177/009286150103500134 . 73036562 .
- Biron P . Withdrawal of oxyphenbutazone: what about phenylbutazone? . CMAJ . 134 . 10 . 1119–20 . May 1986 . 3697857 . 1491052 .
- Web site: Wood . Dave . vanc . 22 May 2008 . Record for the Highest Scoring Scrabble Move . live . https://web.archive.org/web/20230511235136/https://www.scrabulizer.com/blog/post/3 . 11 May 2023 . Scrabulizer.
