azapropazone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory analgesics, phenylbutazone derivatives 266 13539-59-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • AHR-3018
  • apazone dihydrate
  • azapropazone
  • azapropazone dihydrate
  • apazone
  • cinnamin
  • cinnopropazone
  • prolixan
An anti-inflammatory agent used in the treatment of rheumatoid arthritis. It also has uricosuric properties and has been used to treat gout.
  • Molecular weight: 300.36
  • Formula: C16H20N4O2
  • CLOGP: 1.78
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 0
  • TPSA: 56.22
  • ALOGS: -2.66
  • ROTB: 2

Drug dosage:

DoseUnitRoute
0.75 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.15 mg/mL Bocci G, Oprea TI, Benet LZ
EoM (Fraction excreted unchanged in urine) 60 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 89.18 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.14 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.00 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 17 hours Lombardo F, Berellini G, Obach RS
BA (Bioavailability) 83 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.926 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 2.944 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 57.016 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 5.495 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 3.350 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 3.500 % High 1
herg hERG pIC50 4.784 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.403 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 22.336 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 0.570 % High 1
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3B,ITK,JAK2,KIT,MAP3K21,MAP3K7,MAPK7,MARK4,NTRK2,PDK1,PDK2,PDK4,PIK3CB,PIK3CD,PIM2,PLK1,PRKDC,SIK2,STK33,SYK,TEK,TTK 38
kinase-selectivity-class AXL,GRK2 2
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 7.278 High 1
mh-clint Mouse hepatocyte intrinsic clearance 24.266 High 1
mppb Mouse plasma protein binding (% unbound) 1.750 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 30.903 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 3.050 % High 1
rh-clint Rat hepatocyte intrinsic clearance 9.817 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 64.540 % High 1
rppb Rat plasma protein binding (% unbound) 0.680 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 693.426 uM High 1

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1972 YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01AX04 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Other antiinflammatory and antirheumatic agents, non-steroids
MeSH PA D000700 Analgesics
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D006074 Gout Suppressants
MeSH PA D014528 Uricosuric Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:35841 uricosuric drug

Related Drugs by ATC class:

M01AX Other antiinflammatory and antirheumatic agents, non-steroids 13 drugs
benzydaminechondroitin sulfatediacereinfeprazoneglucosaminemorniflumatenabumetoneniflumic acidnimesulideorgoteinoxaceprolproquazone show all 13 →

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Ankylosing spondylitis indication 9631008 DOID:7147
Rheumatoid arthritis indication 69896004 DOID:7148
Gout indication 90560007 DOID:13189
Osteoarthritis indication 396275006




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.24 acidic
pKa2 0.41 Basic

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 WOMBAT-PK
Xanthine dehydrogenase/oxidase Enzyme WOMBAT-PK

External reference:

IDSource
N0000167162 NUI
D02966 KEGG_DRUG
22304-30-9 SECONDARY_CAS_RN
1029 RXNORM
C0003524 UMLSCUI
CHEBI:38010 CHEBI
AZQ PDB_CHEM_ID
CHEMBL1565476 ChEMBL_ID
DB07402 DRUGBANK_ID
26098 PUBCHEM_CID
D001032 MESH_DESCRIPTOR_UI
BF18764H96 UNII
2276 INN_ID
003712 NDDF
329543000 SNOMEDCT_US
391798003 SNOMEDCT_US
BF18764H96 INXIGHT DRUGS

Pharmaceutical products:

None