Compound: phenylbutazone
SMILES: O=C1N(N(c2ccccc2)C(C1CCCC)=O)c3ccccc3
InChIKey: VYMDGNCVAMGZFE-UHFFFAOYSA-N
Synonyms: phenylbutazone, 50-33-9, 4-Butyl-1,2-diphenylpyrazolidine-3,5-dione, Butapirazol, Butazolidin, Butadion, Flexazone, Azolid, Butacote, Butazolidine, Ecobutazone, Fenibutazona, Fenilbutazona, Fenylbutazon, Intrabutazone, Artrizin, Butadiona, Diphebuzol, Fenibutol, Intrazone, Phebuzine, Butoz, Buzon, Diphenylbutazone, Equipalazone, Bute, Phenylbutazonum, Alkabutazona, Alqoverin, Anuspiramin, Arthrizon, Artrizone, Bunetzone, Butacompren, Butagesic, Butalgina, Butalidon, Butapirazole, Butarecbon, Butartril, Butartrina, Butidiona, Butylpyrin, Buvetzone, Chembutazone, Digibutina, Diossidone, Eributazone, Fenibutal, Fenibutasan, Fenilbutina, Fenilbutine, Fenilidina, Mephabutazon, Mephabutazone, Phenbutazol, Phenopyrine, Phenyzone, Praecirheumin, Pyrabutol, Alindor, Anerval, Anpuzone, Artropan, Azobutyl, Benzone, Betazed, Bizolin, Butaluy, Butazina, Butazona, Elmedal, Febuzina, Fenartil, Fenotone, Nadazone, Reumazin, Reumuzol, Robizone, Zolaphen, Busone, Butone, Diozol, Kadol, Lingel, Reudo, Reudox, Uzone, Butiwas-Simple, Equi bute, Exrheudon N, Robizone-V, 4-Butyl-1,2-diphenyl-3,5-pyrazolidinedione, Shigrodin, Tevcodyne, Ia-But, Pirarreumol B, 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine, Bizolin 200, Phenylbutazon, Butatron, Butadionum, Schemergen, Butazone, Phenyzene, Tencodyne, Ticinil, Ambene, Mepha-Butazon, 3,5-Pyrazolidinedione, 4-butyl-1,2-diphenyl-, esteve, Fenilbutazone, 4-BUTYL-1,2-DIPHENYL-PYRAZOLIDINE-3,5-DIONE, R-3-ZON, VAC-10, 3,5-Dioxo-1,2-diphenyl-4-N-butylpyrazolidine, 4-n-Butyl-1,2-diphenyl-3,5-pyrazolidinedione, DA-192, 1,2-Diphenyl-4-butyl-3,5-pyrazolidinedione, G 13,871, 1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine, 1,2-Diphenyl-4-butyl-3,5-dioxopyrazolidine, DTXSID9021136, NCI-C56531, 3,5-Dioxe-4 buty-1, diphenyl-pyrazolidine, GN5P7K3T8S, NSC-25134, G 13871, CHEBI:48574, DTXCID601136, G-13871, Pributazone, Superiorbute, Butaject, Butequine, Equiphar, VetriBute, Butatron Gel, Pro-Bute, EquiBute Injection, Bizolin 1-G, Butazolidin Granules, Tevcodyne Injectable, Equizone 100, EQUIZONE, PHENYLBUTE, Phenylbutazone Boluses, EQUI-PHAR, Bizolin Injection 20%, Phen-Buta Vet Injection, Phen-Buta-Vet Injection, RefChem:929062, Robizone Injectable 20%, EquiBute Tablets 100 mg, Butazolidin Injectable 20%, Phenylbutazone 20% Injection, EQUIZONE 50/100, Bizolin-100, Bizolin-200, M01AA01, M02AA01, Phenylbutazone Tablets, USP 1 gram, Butazolidin Bolus, Butazolidin Tablets, Phen-Buta-Vet Tablets, Phenylbutazone S/A, Phen-Buta Vet Tablets, Phenylbutazone Tablets (Horses), Butazolidin, Butazolidin Paste, Bute, Phenylbute Paste, Phenylzone Paste, Phenylbutazone Tablets, USP 100 mg, Phenylbutazone Tablets, USP 200 mg, 200-029-0, Butapyrazole, Scanbutazone, Intalbut, Ipsoflame, Malgesic, Merizone, Nadozone, Novophenyl, Phebuzin, Phenylbutaz, Pyrazolidin, Rectofasa, Reumasyl, Reumazol, Reupolar, Rubatone, Antadol, Reumune, Neo-zoline, Phenyl-Mobuzon, Robizon-V, Butaphen, Azdid, Buta phen, Schemergin, Wescozone, Tazone, Phen-Buta-Vet, Therazone, Todalgil, Zolidinum, Tetnor, B.t.z., Usaf ge-15, A 7514, 3,5-Dioxo-1,2-diphenyl-4-n-butyl-pyrazolidin, Fenilbutazon, MFCD00005500, MLS000069424, NCI-C55414, s1654, 'Esteve', NCGC00015846-10, NCGC00015846-11, SMR000059073, Fenilbutazone [DCIT], Phenylbutazon [German], P1Z, Fenilbutazona [INN-Spanish], Phenylbutazonum [INN-Latin], Phenyl butazone, CAS-50-33-9, CCRIS 2374, component of Azolid-A, HSDB 3159, 4-butyl-1,2-diphenyl-1,2-diazolidine-3,5-dione, SR-01000000004, AZOLID (TN), EINECS 200-029-0, NSC 25134, UNII-GN5P7K3T8S, BRN 0290080, Alkazone, Phenogel, 50-33-9 (free form), Butapirazole;, Fenylbutazon;, Phenbutazone;, Butazolidin;, Butalidon;, Butacote;, Butadion;, Diphenylbutazone;, Phen-Buta, Pirarreumol 'B', Phenylbutazone CRS, Phenylbutazone [USP:INN:BAN:JAN], 1,5-dioxopyrazolidine, Spectrum_001079, 4-Butyl-1,5-dione, Opera_ID_888, Spectrum2_001282, Spectrum3_000675, Spectrum4_000477, Spectrum5_001335, Lopac-P-8386, Phenylbutazone (Standard), P1686, Epitope ID:124940, P 8386, PHENYLBUTAZONE [MI], SCHEMBL3632, PHENYLBUTAZONE [INN], PHENYLBUTAZONE [JAN], Lopac0_000993, Oprea1_416494, BSPBio_002369, KBioGR_000954, KBioSS_001559, PHENYLBUTAZONE [HSDB], PHENYLBUTAZONE [IARC], MLS001148412, MLS002152929, DivK1c_000331, PHENYLBUTAZONE [VANDF], SPECTRUM1500482, SPBio_001283, PHENYLBUTAZONE [MART.], 1,5-dioxo-4-butylpyrazolidine, 3, 4-butyl-1,2-diphenyl-, 4-Butyl-1,5-dioxopyrazolidine, 4-Butyl-1,5-pyrazolidinedione, GTPL7270, orb1308640, orb3140016, PHENYLBUTAZONE [USP-RS], PHENYLBUTAZONE [WHO-DD], 1,3-dioxo-4-N-butylpyrazoline, HMS501A13, HY-B0230R, KBio1_000331, KBio2_001559, KBio2_004127, KBio2_006695, KBio3_001589, MSK7138, NINDS_000331, Phenylbutazone (JP18/USP/INN), HMS1920H06, HMS2090H17, HMS2091P08, HMS2233B13, HMS3263G07, HMS3369P16, HMS3649M17, HMS3651G15, HMS3715E21, HMS3884C06, HMS5079D08, Pharmakon1600-01500482, Phenylbutazone, analytical standard, component of Azolid-A (Salt/Mix), Phenylbutazone - Bio-X trade mark, PHENYLBUTAZONE [GREEN BOOK], HY-B0230, NSC25134, 3,2-diphenyl-4-N-butylpyrazolidine, PHENYLBUTAZONE [ORANGE BOOK], Tox21_110242, Tox21_110243, Tox21_201809, Tox21_302763, Tox21_500993, 3,2-diphenyl-4-N-butyl-pyrazolidin, AC-683, CCG-39220, EBC-03849, NSC757272, PHENYLBUTAZONE [EP MONOGRAPH], SBB012526, STK388348, PHENYLBUTAZONE [USP MONOGRAPH], AKOS001592731, Phenylbutazone (Butazolidin, Butatron), Tox21_110242_1, DB00812, FP26944, KS-5127, LP00993, NSC-757272, SDCCGSBI-0050966.P005, WLN: T5VNNV EHJ BR& CR& E4, IDI1_000331, NCGC00015846-01, NCGC00015846-02, NCGC00015846-03, NCGC00015846-04, NCGC00015846-05, NCGC00015846-06, NCGC00015846-07, NCGC00015846-08, NCGC00015846-09, NCGC00015846-12, NCGC00015846-13, NCGC00015846-15, NCGC00015846-27, NCGC00023855-03, NCGC00023855-04, NCGC00023855-05, NCGC00023855-06, NCGC00023855-07, NCGC00023855-08, NCGC00181112-01, NCGC00256449-01, NCGC00259358-01, NCGC00261678-01, Phenylbutazone; Suxibuzone EP Impurity A, 4297-92-1, BP166190, ST066897, SBI-0050966.P004, DB-051755, SUXIBUZONE IMPURITY A [EP IMPURITY], EU-0100993, NS00000675, SW199456-2, UNM000001255503, 1,2-diphenyl-3,5-dioxo-4-butyl-pyrazolidine, Phenylbutazone, SAJ special grade, >=99.0%, 1,2-diphenyl-3,5-dioxo-4-n-butylpyrazolidine, C07440, D00510, EN300-126733, 1,2-diphenyl-3,5-dioxo-4-n-butyl-pyrazolidine, AB00052071-15, AB00052071-16, AB00052071_17, AB00052071_18, AG-205/04675049, Q421342, SR-01000000004-2, SR-01000000004-4, SR-01000000004-5, SR-01000000004-9, BRD-K10843433-001-12-8, BRD-K10843433-001-20-1, BRD-K10843433-001-21-9, BRD-K10843433-001-22-7, BRD-K10843433-001-23-5, SR-01000000004-13, Z57355370, Phenylbutazone, TraceCERT(R), certified reference material, Phenylbutazone Working Standard (Secondary Reference Standard), Phenylbutazone, European Pharmacopoeia (EP) Reference Standard, Phenylbutazone, United States Pharmacopeia (USP) Reference Standard, InChI=1/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H
Theoretical properties:
molecular_formula: C19H20N2O2
molecular_weight: 308.4 g/mol
exact_mass: 308.152477885 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 5
heavy_atom_count: 23
topological_polar_surface_area: 40.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from ethanol
color: Crystals from ethanol
odor: ODORLESS
melting_point: 219 to 225 °F (NTP, 1992)
solubility: less than 1 mg/mL at 74.3 °F (NTP, 1992)
Descriptions:
pubchem: Phenylbutazone is a member of the class of pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position. It has a role as a metabolite, a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antirheumatic drug, a peripheral nervous system drug and an EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor.
chebi: A member of the class of  pyrazolidines that is 1,2-diphenylpyrazolidine-3,5-dione carrying a butyl group at the 4-position.
chembl: PHENYLBUTAZONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Phenylbutazone, often referred to as "bute", is a nonsteroidal anti-inflammatory drug (NSAID) for the short-term treatment of pain and fever in animals.
In the United States and United Kingdom, it is no longer approved for human use (except in the United Kingdom for ankylosing spondylitis), as it can cause severe adverse effects such as suppression of white blood cell production and aplastic anemia. This drug was implicated in the 2013 meat adulteration scandal. Positive phenylbutazone tests in horse meat were uncommon in the UK, however.