Phenylbutazone |
![]() Last updated: 15/09/2025 |
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(Also known as: bute; chembutazone ; butazolidine) |
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A non-steroidal anti-inflammatory drug (NSAID) with veterinary applications | |
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Used for the treatment of chronic pain, including the symptoms of arthritis and other musculoskeletal disorders | |
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Horses; Dogs; Cats |
Approval status |
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Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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None | |
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C₁₉H₂₀N₂O₂ | |
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CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3 | |
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No data | |
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VYMDGNCVAMGZFE-UHFFFAOYSA-N | |
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InChI=1S/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,2-3,14H2,1H3 | |
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Yes |
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Common Name | Relationship | Link |
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phenylbutazone | - | ![]() |
General status |
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Analgesic, Anti-inflammatory | |
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Phenylhydrazine | |
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Synthetic | |
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Binds to and inactivates prostaglandin H synthase and prostacyclin synthase through peroxide (H2O2) mediated deactivation. The reduced production of prostaglandin leads to reduced inflammation of the surrounding tissues. | |
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[Prostaglandin G/H synthase 2, Antagonist], [Prostacyclin synthase, Antagonist], [Prostaglandin G/H synthase 1, Antagonist] | |
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50-33-9 | |
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200-029-0 | |
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Musculo-skeletal system: Anti-inflammatory and antirheumatic products, Topical products for joint and muscular pain | |
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QM01AA01; QM02AA01 | |
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No | |
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308.37 | |
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4-butyl-1,2-diphenyl-pyrazolidine-3,5-dione | |
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3,5-dioxo-1,2-diphenyl-4-N-butylpyrazolidine | |
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Powdery solid |
Commercial |
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Current | |||
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Circa mid-1950s, introduced | |||
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Usually available as solutions for injection and various formulations such as powders, tablets and pstes for oral use | |||
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The production of phenylbutazone involves a multi-step chemical synthesis beginning with diethyl-n-butylmalonate and 1,2-diphenylhydrazine as key raw materials. These compounds undergo a condensation reaction to form a hydrazone intermediate, which is then cyclised to yield the pyrazolidinedione core structure characteristic of phenylbutazone. Subsequent steps include alkylation and oxidation to introduce the butyl side chain and refine the molecular framework. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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47.5 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
Moderate | ||||||||
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105 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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3.16 X 1004 | Calculated | - | |||||||
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4.5 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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4.5 | L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source |
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3.95 X 10-05 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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In methanol: 239.5nm | L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source |
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Degradation |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Soil adsorption and mobility |
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Fate indices |
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Known soil and groundwater metabolites |
None
Other known metabolites |
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4-butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione | oxyphenbutazone | - | - |
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Terrestrial ecotoxicology |
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245 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
Moderate | ||||||||
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Aquatic ecotoxicology |
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> 100 | Q3 Q = Miscellaneous data from online sources Danio rerio3 = Unverified data of known source |
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General |
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High (class III) | - | - | ||||||||
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245 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
Moderate | ||||||||
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Intraperitoneal LD₅₀ = 142 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intramuscular LD₅₀ = 220 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Metabolised in the liver and excreted in the urine | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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May cause stomach irritation and vomiting |
Handling issues |
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IMDG Transport Hazard Class 6.1 | |||
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Not listed (Not listed) | |||
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UN2811 | |||
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Packaging Group III (minor danger) | |||
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phenylbutazone | ||
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Phenylbutazon | ||
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fenilbutazona | ||
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Record last updated: | 15/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |