Phenylbutazone
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Also known as AmbeneArtrizinAzolidAntadolBizolinButacoteButadionButadionaButapirazolButatronButazolidinButozBuzonButajectDiphebuzolEcobutazoneEquipalazoneExrheudon nElmedalEquiphar
Summary
Phenylbutazone (CHEMBL101) is an approved small-molecule non-narcotic analgesic (ATC M01AA01) targeting PTGS1, PTGS2, and TAS2R2; indicated across 3 conditions including rheumatic disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: M01AA01 (+1 more)
- Targets: 3 (PTGS1, PTGS2, TAS2R2)
- Indications: 3 conditions
- Chemistry: C19H20N2O2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL101 |
| Name | Phenylbutazone |
| Type | Small molecule |
| Max phase | 4 |
| ChEBI | CHEBI:48574 |
| ATC | M01AA01, M02AA01 |
| Molecular formula | C19H20N2O2 |
| InChIKey | VYMDGNCVAMGZFE-UHFFFAOYSA-N |
SMILES: CCCCC1C(=O)N(c2ccccc2)N(c2ccccc2)C1=O
ChEBI definition: A member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.
Pharmacological roles (ChEBI): non-narcotic analgesic, non-steroidal anti-inflammatory drug, antirheumatic drug, peripheral nervous system drug, EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor.
Other ChEBI roles (chemical / environmental): metabolite.
Also known as: Ambene, Artrizin, Azolid, Antadol, Bizolin, Butacote, Butadion, Butadiona, Butapirazol, Butatron, Butazolidin, Butoz
Parent form; salt/anhydrous children: CHEMBL3137687
Patent coverage: 17,512 distinct patent families (59,455 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
Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).
| Gene | Target | Action | pAffinity | Cancer dependency | UniProt |
|---|---|---|---|---|---|
| PTGS1 | COX-1 | Inhibition | 5.52 | 0% | P23219 |
| PTGS2 | COX-2 | Inhibition | 3.55 | 0% | P35354 |
| TAS2R2 | TAS2R2 | Agonist | Q50KZ9 |
Broader ChEMBL bioactivity targets: 17 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Microtubule-associated protein tau, Survival motor neuron protein, Prelamin-A/C, 4’-phosphopantetheinyl transferase ffp, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Organic anion transporter 3, Cyclooxygenase, Prostaglandin G/H synthase 1, fMet-Leu-Phe receptor.
Bioactivity
ChEMBL activities: 9 potent at pChembl ≥ 5 of 21 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| NAPRT | 10 | Ki | 0.1 | nM | CHEMBL_ACT_19323252 |
| LMNA | 8 | Potency | 10 | nM | CHEMBL_ACT_3651942 |
| NPSR1 | 6.5 | Potency | 316.2 | nM | CHEMBL_ACT_4937242 |
| TDP1 | 6.05 | Potency | 891.3 | nM | CHEMBL_ACT_3927799 |
| ALDH1A1 | 5.95 | Potency | 1122 | nM | CHEMBL_ACT_4194845 |
| SMN1 | 5.8 | Potency | 1585 | nM | CHEMBL_ACT_3904461 |
| PTGS1 | 5.52 | IC50 | 3000 | nM | CHEMBL_ACT_807130 |
| HSD17B10 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4861435 |
| FPR1 | 5.28 | Ki | 5300 | nM | CHEMBL_ACT_14249101 |
Target pathways
Aggregated over 3 target gene(s): PTGS1, PTGS2, TAS2R2.
Top Reactome pathways
9 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Synthesis of Prostaglandins (PG) and Thromboxanes (TX) | 2 | PTGS1, PTGS2 |
| COX reactions | 1 | PTGS1 |
| Synthesis of 15-eicosatetraenoic acid derivatives | 1 | PTGS2 |
| Interleukin-10 signaling | 1 | PTGS2 |
| Interleukin-4 and Interleukin-13 signaling | 1 | PTGS2 |
| Biosynthesis of DHA-derived SPMs | 1 | PTGS2 |
| Biosynthesis of EPA-derived SPMs | 1 | PTGS2 |
| Biosynthesis of DPAn-3 SPMs | 1 | PTGS2 |
| Biosynthesis of electrophilic ω-3 PUFA oxo-derivatives | 1 | PTGS2 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| prostaglandin biosynthetic process | 2 |
| response to oxidative stress | 2 |
| regulation of blood pressure | 2 |
| cyclooxygenase pathway | 2 |
| regulation of cell population proliferation | 2 |
| long-chain fatty acid biosynthetic process | 2 |
| lipid metabolic process | 2 |
| fatty acid metabolic process | 2 |
| fatty acid biosynthetic process | 2 |
| prostaglandin metabolic process | 2 |
| prostanoid biosynthetic process | 2 |
| cellular oxidant detoxification | 2 |
| embryo implantation | 1 |
| response to nematode | 1 |
| response to selenium ion | 1 |
Indications & clinical
Indications
3 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| rheumatic disorder | 4 | MONDO:0005554 | EFO:0005755 |
2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 0.
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
Related molecules
Related molecules
Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.
407 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| 3,3’,4’,5-TETRACHLOROSALICYLANILIDE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| ACEMETACIN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| ASPIRIN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| BROMFENAC | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| CAPSAICIN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| CAPTOPRIL | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| CARPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| CELECOXIB | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| CIANIDANOL | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| DEXIBUPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| DEXKETOPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| DICLOFENAC | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| DOXORUBICIN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| ESFLURBIPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| ETODOLAC | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| ETORICOXIB | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| FLURBIPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| GLAFENINE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| HEXACHLOROPHENE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| IBUPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| INDOMETHACIN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| KETOPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| KETOROLAC | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| LEVODOPA | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| LOXOPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| LUMIRACOXIB | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| MECLOFENAMIC ACID | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| MEFENAMIC ACID | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| MELOXICAM | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| MOFEZOLAC | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| MONOBENZONE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| NAPROXEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| NIMESULIDE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| OMADACYCLINE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| OXAPROZIN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| PIROXICAM | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| PRIMAQUINE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| RANITIDINE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| ROFECOXIB | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| SELINEXOR | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| SUPROFEN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| TEGASEROD | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| TELOTRISTAT | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| TOLMETIN | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| TROGLITAZONE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| VALDECOXIB | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| VORTIOXETINE | ChEMBL | Phase 4 (approved) | PTGS1, PTGS2 |
| CURCUMIN | ChEMBL | Phase 3 | PTGS1, PTGS2 |
| RESVERATROL | ChEMBL | Phase 3 | PTGS1, PTGS2 |
| CIMICOXIB | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| DERACOXIB | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| ENOFELAST | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| FIROCOXIB | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| FLUFENAMIC ACID | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| LICOFELONE | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| MAVACOXIB | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| MIROPROFEN | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| NIFLUMIC ACID | ChEMBL | Phase 2 | PTGS1, PTGS2 |
| PHENOTHIAZINE | ChEMBL | Phase 2 | PTGS1, PTGS2 |
Related Atlas pages
- Genes: PTGS1, PTGS2, TAS2R2
- Diseases: rheumatic disorder
- Drugs: 3,3’,4’,5-TETRACHLOROSALICYLANILIDE, Acemetacin, Aspirin, Bromfenac, Capsaicin, Captopril, Carprofen, Celecoxib, Cianidanol, Dexibuprofen, Dexketoprofen, Diclofenac, Diethylstilbestrol, Doxorubicin, Esflurbiprofen, Etodolac, Etoricoxib, Flurbiprofen, Glafenine, Hexachlorophene, Ibuprofen, Indomethacin, Ketorolac, Levodopa, Loxoprofen, Lumiracoxib, Meclofenamic Acid, Mefenamic Acid, Meloxicam, Mofezolac, Monobenzone, Naproxen, Nimesulide, Omadacycline, Oxaprozin, Piroxicam, Primaquine, Ranitidine, Rofecoxib, Selinexor, Suprofen, Tegaserod, Telotristat, Tolmetin, Troglitazone, Valdecoxib, Vortioxetine, Curcumin, Resveratrol