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

Stem definitionDrug idCAS RN
2115 62-44-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • phenacetin
  • acetophenetidin
  • acetophenetidine
  • acetophenetin
  • acetphenetidin
  • phenacetine
  • phenazetin
A phenylacetamide that was formerly used in ANALGESICS but nephropathy and METHEMOGLOBINEMIA led to its withdrawal from the market. (From Smith and Reynard, Textbook of Pharmacology,1991, p431)
  • Molecular weight: 179.22
  • Formula: C10H13NO2
  • CLOGP: 1.76
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 38.33
  • ALOGS: -2
  • ROTB: 3

Drug dosage:

DoseUnitRoute
1.80 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.76 mg/mL Bocci G, Oprea TI, Benet LZ
MRTD (Maximum Recommended Therapeutic Daily Dose) 278.99 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 25 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.40 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 21 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.47 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.92 hours Lombardo F, Berellini G, Obach RS

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.554 High 0.89
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.902 High 0.89
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 78.524 10^-6 cm/s High 0.89
dh-clint Dog hepatocyte intrinsic clearance 18.408 uL/min/10^6 cells High 0.89
dppb Dog plasma protein binding (% unbound) 68.730 % High 0.89
fcs-ppb Fetal calf serum protein binding (% unbound) 72.870 % High 0.89
herg hERG pIC50 3.768 pIC50 High 0.89
hh-clint Human hepatocyte intrinsic clearance 5.598 uL/min/10^6 cells High 0.89
hlm-clint Human liver microsomal intrinsic clearance 19.011 uL/min/mg protein High 0.89
hppb Human plasma protein binding (% unbound) 63.420 % High 0.89
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3B,IKBKB,ITK,JAK1,JAK2,MAP2K6,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MET,MTOR,NTRK2,PAK4,PDK1,PDK2,PDK4,PDPK1,PIK3CB,PIK3CG,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TTK 47
kinase-selectivity-class AURKA,AXL,BRAF,DDR1,ERBB2,GRK2,PDK4,STK33 8
mdck-mdr1-bcrp-efflux MDCK-MDR1-BCRP efflux ratio 0.551 High 1
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.581 High 0.89
mh-clint Mouse hepatocyte intrinsic clearance 101.158 High 0.89
mppb Mouse plasma protein binding (% unbound) 67.680 High 0.89
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.486 High 0.89
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 67.680 % High 0.89
rat-kpuu-brain Rat brain Kpuu 0.964 % High 1
rh-clint Rat hepatocyte intrinsic clearance 15.066 uL/min/10^6 cells High 0.89
rh-fuinc Rat hepatocyte fraction unbound in incubation 95.660 % High 0.89
rppb Rat plasma protein binding (% unbound) 57.990 % High 0.89
solubility-dd Solubility at pH 7.4 in DMSO 847.227 uM High 0.89

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1887 YEAR INTRODUCED

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Adulterated product 157.91 130.61 22 333 744 42620236
Toxicity to various agents 143.06 130.61 57 298 229079 42391901

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 187.79 134.26 69 359 480486 110108385
Adulterated product 165.61 134.26 22 406 1133 110587738

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N02BE03 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Anilides
ATC N02BE53 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Anilides
ATC N02BE73 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Anilides
MeSH PA D000700 Analgesics
MeSH PA D018689 Sensory System Agents
MeSH PA D018712 Analgesics, Non-Narcotic
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:49110 peripheral nervous system drug
CHEBI has role CHEBI:73263 cyclooxygenase 3 inhibitor

Related Drugs by ATC class:

N02BE Anilides 3 drugs
bucetinparacetamolpropacetamol

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

DiseaseRelationSNOMED_IDDOID
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Suicidal thoughts contraindication 6471006
Alcoholism contraindication 7200002
Hyperammonemia contraindication 9360008
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Hepatic encephalopathy contraindication 13920009 DOID:13413
Depressive disorder contraindication 35489007
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Hyperactive behavior contraindication 44548000
Conduction disorder of the heart contraindication 44808001
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Substance abuse contraindication 66214007
Agoraphobia contraindication 70691001 DOID:593
Hepatic coma contraindication 72836002 DOID:12550
Sleep apnea contraindication 73430006 DOID:0050847
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hemophilia contraindication 90935002
Anemia due to enzyme deficiency contraindication 111577008
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Sleep automatism contraindication 247962006
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Panic disorder contraindication 371631005 DOID:594
Respiratory insufficiency contraindication 409623005
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Myocardial infarction in recovery phase contraindication 418044006
Porphyria contraindication 418470004
Acute erosive gastritis contraindication 444926003
Acute exacerbation of asthma contraindication 708038006




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

None

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

External reference:

IDSource
4020336 VUID
N0000148179 NUI
D00569 KEGG_DRUG
4020336 VANDF
C0031364 UMLSCUI
CHEBI:8050 CHEBI
N4E PDB_CHEM_ID
CHEMBL16073 ChEMBL_ID
DB03783 DRUGBANK_ID
D010615 MESH_DESCRIPTOR_UI
4754 PUBCHEM_CID
412 INN_ID
7402 IUPHAR_LIGAND_ID
ER0CTH01H9 UNII
8113 RXNORM
NOCODE MMSL
001606 NDDF
ER0CTH01H9 INXIGHT DRUGS

Pharmaceutical products:

None