phenylbutazone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory analgesics, phenylbutazone derivatives 2145 50-33-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • phenylbutazone
  • phenylbutazon
A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.
  • Molecular weight: 308.38
  • Formula: C19H20N2O2
  • CLOGP: 3.38
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 0
  • TPSA: 40.62
  • ALOGS: -3.33
  • ROTB: 5

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.30 g O
0.30 g P
0.30 g R

ADMET properties:

PropertyValueReference
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 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Jan. 10, 1980 FDA SANDOZ

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
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 D018712 Analgesics, Non-Narcotic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:25212 metabolites
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drugs
CHEBI has role CHEBI:35842 antirheumatic agent
CHEBI has role CHEBI:49110 peripheral nervous system agent
CHEBI has role CHEBI:73136 nadph2-dependent carbonyl reductase inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Gout off-label use 90560007 DOID:13189

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.62 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 5.52 CHEMBL CHEMBL
Cytochrome P450 2C9 Enzyme Ki 4.72 WOMBAT-PK
Prostacyclin synthase Enzyme WOMBAT-PK
fMet-Leu-Phe receptor GPCR IC50 4.69 WOMBAT-PK
Cyclooxygenase Enzyme IC50 4.82 CHEMBL
Cyclooxygenase 2; Prostaglandin G/H synthase-2; Uncharacterized protein Enzyme IC50 5.42 CHEMBL

External reference:

IDSource
4018391 VUID
N0000146718 NUI
D00510 KEGG_DRUG
4018391 VANDF
C0031463 UMLSCUI
CHEBI:48574 CHEBI
P1Z PDB_CHEM_ID
CHEMBL101 ChEMBL_ID
D010653 MESH_DESCRIPTOR_UI
DB00812 DRUGBANK_ID
7270 IUPHAR_LIGAND_ID
4 INN_ID
GN5P7K3T8S UNII
4781 PUBCHEM_CID
8160 RXNORM
NOCODE MMSL
d00341 MMSL
002375 NDDF
273951003 SNOMEDCT_US
48351000 SNOMEDCT_US

Pharmaceutical products:

None