Oxyphenbutazone Anhydrous

Summary

Oxyphenbutazone Anhydrous (CHEMBL1228) is an approved small-molecule non-steroidal anti-inflammatory drug.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Chemistry: 324.4 Da · C19H20N2O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1228
Name	Oxyphenbutazone Anhydrous
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	4641
ChEBI	CHEBI:76258
Molecular formula	C19H20N2O3
Molecular weight	324.4
InChIKey	HFHZKZSRXITVMK-UHFFFAOYSA-N

SMILES: CCCCC1C(=O)N(N(C1=O)C2=CC=C(C=C2)O)C3=CC=CC=C3

IUPAC name: 4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione

ChEBI definition: 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 Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.

Pharmacological roles (ChEBI): non-steroidal anti-inflammatory drug, non-narcotic analgesic, antipyretic, gout suppressant, antineoplastic agent, antimicrobial agent.

Other ChEBI roles (chemical / environmental): drug metabolite, xenobiotic metabolite.

Also known as: Californit, Crovaril, Flogitolo, Flogoril, Frabel, G-27202, Neo-farmadol, NSC-526053, Oxalid, Oxyphenbutazone anhydrous, Rapostan, Reozon

Parent form; salt/anhydrous children: CHEMBL3989676

Patent coverage: 6,385 distinct patent families (24,044 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 11 (assay-derived). Sample: Microtubule-associated protein tau, Nuclear receptor ROR-gamma, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Ras-related protein Rab-9A, Solute carrier family 22 member 6, Beta-lactamase, Prostaglandin G/H synthase 1, Cytochrome P450 3A4, Aldehyde dehydrogenase 1A1, Cellular tumor antigen p53, Nicotinate phosphoribosyltransferase.

Bioactivity

ChEMBL activities: 5 potent at pChembl ≥ 5 of 15 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
NAPRT	9.52	Ki	0.3	nM	CHEMBL_ACT_19323247
P51450	5.35	Potency	4467	nM	CHEMBL_ACT_4815234
P51450	5.25	Potency	5623	nM	CHEMBL_ACT_4089367
RAB9A	5.2	Potency	6310	nM	CHEMBL_ACT_3849821
PTGS1	5.11	AC50	7796	nM	CHEMBL_ACT_25204936

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

0 indication records carry no mapped disease name (EFO/MeSH-only); none shown.

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).