AntibioticMech

oxyphenbutazone

CHEBI:76258 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome. — ChEBI

Classification

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:33853 CHEBI:33853
• CHEBI:38312 CHEBI:38312

Chemical structure

Computed structure properties

Molecular formula	C19H20N2O3
Charge	0
Average mass	324.38 Da
Monoisotopic mass	324.14739 Da
Source	ChEBI
InChIKey	HFHZKZSRXITVMK-UHFFFAOYSA-N

SMILES

CCCCC1C(=O)N(c2ccccc2)N(c2ccc(O)cc2)C1=O

InChI

InChI=1S/C19H20N2O3/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

Also called

• oxifenbutazona (INN)— chebi
• oxyphenbutazonum (INN)— chebi
• 1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione (EXACT_SYNONYM)— chebi
• 1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine (EXACT_SYNONYM)— chebi
• 1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-n-butylpyrazolidine (EXACT_SYNONYM)— chebi
• 3,5-Dioxo-1-phenyl-2-(p-hydroxyphenyl)-4-N-butylpyrazolidene (EXACT_SYNONYM)— chebi
• 4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione (EXACT_SYNONYM)— chebi
• 4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione (EXACT_SYNONYM)— chebi
• 4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine (EXACT_SYNONYM)— chebi
• 4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione (EXACT_SYNONYM)— chebi
• Hydroxyphenylbutazon (EXACT_SYNONYM)— chebi
• Oxi-fenibutol (EXACT_SYNONYM)— chebi
• Oxifenylbutazon (EXACT_SYNONYM)— chebi
• Oxiphenbutazonum (EXACT_SYNONYM)— chebi
• Oxyphenylbutazone (EXACT_SYNONYM)— chebi
• p-Hydroxyphenylbutazone (EXACT_SYNONYM)— chebi
• p-Oxyphenylbutazone (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• cas:129-20-4
• drugbank:DB03585
• drugcentral:2036
• kegg.compound:C19494
• kegg.drug:D08324
• lincs.smallmolecule:LSM-5029
• patent:EP642336
• patent:US2008014272
• patent:WO2005107748
• reaxys:307474
• wikipedia.en:Oxyphenbutazone

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• CHEBI:33281 CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record

Source	Native ID	Label	Minted CURIE	Version
CHEBI	CHEBI:76258	oxyphenbutazone	antibioticmech:chebi-25f84cf54d	2026-08-30

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.