Oxyphenbutazone

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

Oxyphenbutazone

Clinical data
Trade names	Tandearil, Tanderil
AHFS/Drugs.com	International Drug Names
ATC code	M01AA03 (WHO) M02AA04 (WHO) S01BC02 (WHO)
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Legal status	AU: Withdrawn UK: Withdrawn US: Withdrawn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	129-20-4 Y
PubChem CID	104811
DrugBank	DB03585 Y
ChemSpider	94610 Y
UNII	A7D84513GV
KEGG	D08324 Y
ChEBI	CHEBI:76258 N
ChEMBL	ChEMBL1228 N
CompTox Dashboard (EPA)	DTXSID1045291
ECHA InfoCard	100.004.489
Chemical and physical data
Formula	C19H20N2O3
Molar mass	324.380 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic 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It was withdrawn from markets worldwide in the mid-1980s due to bone marrow suppression and the risk of Stevens–Johnson syndrome.^[3][4]

In Scrabble, the word "oxyphenbutazone" is known for being used in a 1,785-point play — a world record score and the highest known to date.^[5] However, according to Mental Floss, there is no documentation that the word "oxyphenbutazone" has ever been successfully played on a Scrabble board, and it "probably never will be".^[6]