Oxyphenbutazone
Chemical compound
- M01AA03 (WHO) M02AA04 (WHO) S01BC02 (WHO)
- AU: Withdrawn
- UK: Withdrawn
- US: Withdrawn
- (RS)-4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
- 129-20-4 Y
- 104811
- DB03585 Y
- 94610 Y
- A7D84513GV
- D08324 Y
- CHEBI:76258 N
- ChEMBL1228 N
- DTXSID1045291
- Interactive image
- 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
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It was withdrawn from markets worldwide in mid-1980s due to bone marrow suppression and the risk of Stevens–Johnson syndrome.[3][4]
References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ Biron P (May 1986). "Withdrawal of oxyphenbutazone: what about phenylbutazone?". CMAJ. 134 (10): 1119–20. PMC 1491052. PMID 3697857.
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Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; †withdrawn drugs; ‡veterinary use.
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