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phenylbutazone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| anti-inflammatory analgesics, phenylbutazone derivatives | 2145 | 50-33-9 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.30 | g | O |
| 0.30 | g | P |
| 0.30 | g | R |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| BDDCS (Biopharmaceutical Drug Disposition Classification System) | 1 | Benet LZ, Broccatelli F, Oprea TI |
| S (Water solubility) | 0.70 mg/mL | Benet LZ, Broccatelli F, Oprea TI |
| EoM (Fraction excreted unchanged in urine) | 1 % | Benet LZ, Broccatelli F, Oprea TI |
| MRTD (Maximum Recommended Therapeutic Daily Dose) | 32.43 µM/kg/day | Contrera JF, Matthews EJ, Kruhlak NL, Benz RD |
| BA (Bioavailability) | 90 % | Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | 1.161 | High | 1 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 1.012 | High | 1 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 119.950 | 10^-6 cm/s | High | 1 |
| dh-clint | Dog hepatocyte intrinsic clearance | 7.745 | uL/min/10^6 cells | High | 1 |
| dppb | Dog plasma protein binding (% unbound) | 1.830 | % | High | 1 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 1.850 | % | High | 1 |
| herg | hERG pIC50 | 4.424 | pIC50 | High | 1 |
| hh-clint | Human hepatocyte intrinsic clearance | 4.710 | uL/min/10^6 cells | High | 1 |
| hlm-clint | Human liver microsomal intrinsic clearance | 14.256 | uL/min/mg protein | High | 1 |
| hppb | Human plasma protein binding (% unbound) | 0.840 | % | High | 1 |
| kinase-safety-class | ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK2,MAP3K21,MAP3K7,MAPK7,MAPK9,MARK4,MET,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CD,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,TTK | 41 | |||
| kinase-selectivity-class | AXL,GRK2 | 2 | |||
| mdck-mdr1-bcrp-efflux | MDCK-MDR1-BCRP efflux ratio | 1.119 | High | 0.87 | |
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 2.350 | High | 1 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 18.664 | High | 1 | |
| mppb | Mouse plasma protein binding (% unbound) | 1.880 | High | 1 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 1.387 | High | 1 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pppb | Pig plasma protein binding (% unbound) | 1.140 | % | High | 1 |
| rat-kpuu-brain | Rat brain Kpuu | 0.871 | % | High | 0.87 |
| rh-clint | Rat hepatocyte intrinsic clearance | 6.918 | uL/min/10^6 cells | High | 1 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 61.310 | % | High | 1 |
| rppb | Rat plasma protein binding (% unbound) | 0.630 | % | High | 1 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 866.962 | uM | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Jan. 10, 1980 | FDA | SANDOZ |
FDA Adverse Event Reporting System (Female)
None
FDA Adverse Event Reporting System (Male)
None
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Regurgitation | 76.10 | 73.20 | 12 | 241 | 3473 | 110585573 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | M01AA01 | MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS Butylpyrazolidines |
| ATC | M01BA01 | MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS ANTIINFLAMMATORY/ANTIRHEUMATIC AGENTS IN COMBINATION Antiinflammatory/antirheumatic agents in combination with corticosteroids |
| ATC | M02AA01 | MUSCULO-SKELETAL SYSTEM TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN Antiinflammatory preparations, non-steroids for topical use |
| MeSH PA | D000700 | Analgesics |
| MeSH PA | D000893 | Anti-Inflammatory Agents |
| MeSH PA | D000894 | Anti-Inflammatory Agents, Non-Steroidal |
| MeSH PA | D018501 | Antirheumatic Agents |
| MeSH PA | D018689 | Sensory System Agents |
| MeSH PA | D018712 | Analgesics, Non-Narcotic |
| CHEBI has role | CHEBI:25212 | metabolite |
| CHEBI has role | CHEBI:35475 | non-steroidal anti-inflammatory drug |
| CHEBI has role | CHEBI:35481 | non-narcotic analgesic |
| CHEBI has role | CHEBI:35842 | antirheumatic drug |
| CHEBI has role | CHEBI:49110 | peripheral nervous system drug |
| CHEBI has role | CHEBI:73136 | EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor |
Related Drugs by ATC class:
M01AA Butylpyrazolidines 4 drugs
M01BA Antiinflammatory/antirheumatic agents in combination with corticosteroids 2 drugs
M02AA Antiinflammatory preparations, non-steroids for topical use 28 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| Gout | off-label use | 90560007 | DOID:13189 |
🐶 Veterinary Drug Use
| Species | Use | Relation |
|---|---|---|
| Dogs | Inflammatory conditions associated with a musculoskeletal system | Indication |
| Horses | Inflammatory conditions associated with a musculoskeletal system | Indication |
🐶 Veterinary products
| Product | Applicant | Ingredients |
|---|---|---|
| Butazolidin Bolus, Butazolidin Tablets | Intervet Inc. | 1 |
| Butazolidin Injectable 20% | Intervet Inc. | 1 |
| Butazolidin Granules | Intervet Inc. | 1 |
| Butatron | Bimeda Animal Health Limited | 1 |
| Tevcodyne Injectable | Elanco US Inc. | 1 |
| EquiBute Injection | Zoetis Inc. | 1 |
| EquiBute Tablets 100 mg | Zoetis Inc. | 1 |
| Phen-Buta Vet Injection | Bimeda Animal Health Limited | 1 |
| Bizolin-100, Bizolin-200 | Cronus Pharma Specialities India Private Limited | 1 |
| Phen-Buta Vet Tablets, Phenylbutazone Tablets (Horses) | Bimeda Animal Health Limited | 1 |
| Robizone-V | Zoetis Inc. | 1 |
| Phenylbutazone Tablets, USP 1 gram | Elanco US Inc. | 1 |
| Robizone-V | Zoetis Inc. | 1 |
| Bizolin Injection 20% | Cronus Pharma Specialities India Private Limited | 1 |
| Phenylbutazone Tablets, USP 100 mg, Phenylbutazone Tablets, USP 200 mg | Cronus Pharma Specialities India Private Limited | 1 |
| Phen-Buta-Vet Injection | Bimeda Animal Health Limited | 1 |
| Phen-Buta-Vet Tablets, Phenylbutazone S/A | Bimeda Animal Health Limited | 1 |
| Robizone Injectable 20% | Zoetis Inc. | 1 |
| Bizolin 1-G | Cronus Pharma Specialities India Private Limited | 1 |
| Equipalazone | Vetoquinol N.-A. Inc. | 1 |
| Butazolidin, Butazolidin Paste, Bute, Phenylbute Paste, Phenylzone Paste | Intervet Inc. | 1 |
| Butatron Gel | Bimeda Animal Health Limited | 1 |
| Phenylbutazone 20% Injection | Elanco US Inc. | 1 |
| Butequine | Vetoquinol USA Inc. | 1 |
| Superiorbute | Superior Equine Pharmaceuticals Inc. | 1 |
| Equizone 100 | A & G Pharmaceuticals Inc. | 1 |
| Phenylbutazone 20% Injection | Sparhawk Laboratories Inc. | 1 |
| Pributazone | First Priority Inc. | 1 |
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 4.62 | acidic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| Prostaglandin G/H synthase 1 | Enzyme | INHIBITOR | IC50 | 5.52 | CHEMBL | CHEMBL | |||
| fMet-Leu-Phe receptor | GPCR | IC50 | 4.69 | WOMBAT-PK | |||||
| Prostacyclin synthase | Enzyme | WOMBAT-PK | |||||||
| Cytochrome P450 2C9 | Enzyme | Ki | 4.72 | WOMBAT-PK | |||||
| Nicotinate phosphoribosyltransferase | Enzyme | Ki | 10 | CHEMBL | |||||
| Cyclooxygenase 2; Prostaglandin G/H synthase-2; Uncharacterized protein | Enzyme | IC50 | 5.42 | CHEMBL | |||||
| Cyclooxygenase | Enzyme | IC50 | 4.82 | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 4018391 | VUID |
| N0000146718 | NUI |
| D00510 | KEGG_DRUG |
| 4018391 | VANDF |
| C0031463 | UMLSCUI |
| CHEBI:48574 | CHEBI |
| CHEMBL101 | ChEMBL_ID |
| DB00812 | DRUGBANK_ID |
| D010653 | MESH_DESCRIPTOR_UI |
| 4781 | PUBCHEM_CID |
| 7270 | IUPHAR_LIGAND_ID |
| 4 | INN_ID |
| GN5P7K3T8S | UNII |
| 8160 | RXNORM |
| NOCODE | MMSL |
| d00341 | MMSL |
| 002375 | NDDF |
| 273951003 | SNOMEDCT_US |
| 48351000 | SNOMEDCT_US |
| P1Z | PDB_CHEM_ID |
| GN5P7K3T8S | INXIGHT DRUGS |
Pharmaceutical products:
None