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Identification
NamePhenacetin
Accession NumberDB03783  (EXPT03306, DB08243)
TypeSmall Molecule
GroupsWithdrawn
DescriptionPhenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney).
Structure
Thumb
Synonyms
Acetophenetidin
Acetophenetidine
Acetophenetin
Acetphenetidin
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AchrocidinNot Available
CodempiralNot Available
CommotionalNot Available
ContradolNot Available
ContradouleurNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIER0CTH01H9
CAS number62-44-2
WeightAverage: 179.2157
Monoisotopic: 179.094628665
Chemical FormulaC10H13NO2
InChI KeyCPJSUEIXXCENMM-UHFFFAOYSA-N
InChI
InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
IUPAC Name
N-(4-ethoxyphenyl)acetamide
SMILES
CCOC1=CC=C(NC(C)=O)C=C1
Pharmacology
IndicationUsed principally as an analgesic.
Structured Indications Not Available
PharmacodynamicsPhenacetin was the first NSAID and fever reducer to go on the market. Its analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action of the heart, where it acts as a negative inotrope. It is an antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat rheumatoid arthritis (subacute type), intercostal neuralgia, and some forms of ataxia. [Wikipedia]
Mechanism of actionPhenacetin's analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action on the heart, where it acts as a negative inotrope. It is an antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat rheumatoid arthritis (subacute type) and intercostal neuralgia. [Wikipedia]
TargetKindPharmacological actionActionsOrganismUniProt ID
Prostaglandin G/H synthase 1ProteinunknownNot AvailableHumanP23219 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Metabolised in the body to paracetamol.

SubstrateEnzymesProduct
Phenacetin
acetaminophenDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAcute oral toxicity (LD50): 866 mg/kg [Mouse].
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Phenacetin can be increased when it is combined with Abiraterone.Approved
AmiodaroneThe metabolism of Phenacetin can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Phenacetin can be increased when it is combined with Aprepitant.Approved, Investigational
ArmodafinilThe metabolism of Phenacetin can be decreased when combined with Armodafinil.Approved, Investigational
ArtemetherThe metabolism of Phenacetin can be decreased when combined with Artemether.Approved
AtazanavirThe metabolism of Phenacetin can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Phenacetin can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Phenacetin can be decreased when combined with Azithromycin.Approved
BetaxololThe metabolism of Phenacetin can be decreased when combined with Betaxolol.Approved
BexaroteneThe serum concentration of Phenacetin can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Phenacetin can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Phenacetin can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Phenacetin can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe metabolism of Phenacetin can be decreased when combined with Bupropion.Approved
CaffeineThe metabolism of Phenacetin can be decreased when combined with Caffeine.Approved
CapecitabineThe metabolism of Phenacetin can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Phenacetin can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Phenacetin can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Phenacetin can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Phenacetin can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineThe metabolism of Phenacetin can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Phenacetin can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Phenacetin can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Phenacetin can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Phenacetin can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Phenacetin can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Phenacetin can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Phenacetin can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Phenacetin can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Phenacetin can be decreased when combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe metabolism of Phenacetin can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Phenacetin can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Phenacetin can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Phenacetin can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Phenacetin can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Phenacetin can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Phenacetin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Phenacetin can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Phenacetin can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe metabolism of Phenacetin can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Phenacetin can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Phenacetin can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Phenacetin can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Phenacetin can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Phenacetin can be decreased when combined with Desipramine.Approved
DexamethasoneThe serum concentration of Phenacetin can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DihydroergotamineThe metabolism of Phenacetin can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Phenacetin can be decreased when combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Phenacetin can be decreased when combined with Diphenhydramine.Approved
DisulfiramThe metabolism of Phenacetin can be decreased when combined with Disulfiram.Approved
DoxycyclineThe metabolism of Phenacetin can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Phenacetin can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Phenacetin can be decreased when combined with Duloxetine.Approved
EfavirenzThe serum concentration of Phenacetin can be decreased when it is combined with Efavirenz.Approved, Investigational
EliglustatThe metabolism of Phenacetin can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Phenacetin can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Phenacetin can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Phenacetin can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Phenacetin can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe serum concentration of Phenacetin can be decreased when it is combined with Etravirine.Approved
FloxuridineThe metabolism of Phenacetin can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Phenacetin can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Phenacetin can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Phenacetin can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe metabolism of Phenacetin can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Phenacetin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Phenacetin can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Phenacetin can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Phenacetin can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Phenacetin can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe metabolism of Phenacetin can be decreased when combined with Gemfibrozil.Approved
HaloperidolThe metabolism of Phenacetin can be decreased when combined with Haloperidol.Approved
IdelalisibThe serum concentration of Phenacetin can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Phenacetin can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Phenacetin can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Phenacetin can be decreased when combined with Indinavir.Approved
IrbesartanThe metabolism of Phenacetin can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Phenacetin can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Phenacetin can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Phenacetin can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Phenacetin can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Phenacetin can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Phenacetin can be decreased when combined with Ketoconazole.Approved, Investigational
LeflunomideThe metabolism of Phenacetin can be decreased when combined with Leflunomide.Approved, Investigational
LidocaineThe metabolism of Phenacetin can be decreased when combined with Lidocaine.Approved, Vet Approved
LopinavirThe metabolism of Phenacetin can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Phenacetin can be decreased when combined with Lorcaserin.Approved
LosartanThe metabolism of Phenacetin can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Phenacetin can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Phenacetin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Phenacetin can be decreased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Phenacetin can be decreased when combined with Lumefantrine.Approved
MethadoneThe metabolism of Phenacetin can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Phenacetin can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe metabolism of Phenacetin can be decreased when combined with Metoprolol.Approved, Investigational
MexiletineThe metabolism of Phenacetin can be decreased when combined with Mexiletine.Approved
MifepristoneThe serum concentration of Phenacetin can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe metabolism of Phenacetin can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Phenacetin can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Phenacetin can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of Phenacetin can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Phenacetin can be decreased when it is combined with Nafcillin.Approved
NefazodoneThe metabolism of Phenacetin can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Phenacetin can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Phenacetin can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Phenacetin can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Phenacetin can be decreased when combined with Nicardipine.Approved
NicotineThe metabolism of Phenacetin can be decreased when combined with Nicotine.Approved
NilotinibThe metabolism of Phenacetin can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Phenacetin can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Phenacetin can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Phenacetin can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Phenacetin can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Phenacetin can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Phenacetin can be decreased when combined with Pantoprazole.Approved
ParoxetineThe metabolism of Phenacetin can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Phenacetin can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Phenacetin can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Phenacetin can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Phenacetin can be increased when combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe metabolism of Phenacetin can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Phenacetin can be increased when combined with Primidone.Approved, Vet Approved
PromazineThe metabolism of Phenacetin can be decreased when combined with Promazine.Approved, Vet Approved
PyrimethamineThe metabolism of Phenacetin can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinidineThe metabolism of Phenacetin can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Phenacetin can be decreased when combined with Quinine.Approved
RanolazineThe metabolism of Phenacetin can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Phenacetin can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Phenacetin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Phenacetin can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Phenacetin can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Phenacetin can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Phenacetin can be decreased when combined with Ropinirole.Approved, Investigational
SaquinavirThe metabolism of Phenacetin can be decreased when combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Phenacetin can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Phenacetin can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Phenacetin can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Phenacetin can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Phenacetin can be increased when it is combined with Simeprevir.Approved
SorafenibThe metabolism of Phenacetin can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Phenacetin can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Phenacetin can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Phenacetin can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Phenacetin can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Phenacetin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Phenacetin can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Phenacetin can be decreased when combined with Telithromycin.Approved
TenofovirThe metabolism of Phenacetin can be decreased when combined with Tenofovir.Approved, Investigational
TerbinafineThe metabolism of Phenacetin can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TeriflunomideThe serum concentration of Phenacetin can be decreased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Phenacetin can be decreased when combined with Theophylline.Approved
ThioridazineThe metabolism of Phenacetin can be decreased when combined with Thioridazine.Approved
TicagrelorThe metabolism of Phenacetin can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Phenacetin can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Phenacetin can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Phenacetin can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Phenacetin can be decreased when combined with Tolbutamide.Approved
TopiramateThe metabolism of Phenacetin can be decreased when combined with Topiramate.Approved
TranylcypromineThe metabolism of Phenacetin can be decreased when combined with Tranylcypromine.Approved
TrimethoprimThe metabolism of Phenacetin can be decreased when combined with Trimethoprim.Approved, Vet Approved
Valproic AcidThe metabolism of Phenacetin can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Phenacetin can be decreased when combined with Valsartan.Approved, Investigational
VemurafenibThe serum concentration of Phenacetin can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Phenacetin can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Phenacetin can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Phenacetin can be decreased when combined with Voriconazole.Approved, Investigational
ZafirlukastThe metabolism of Phenacetin can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Phenacetin can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

Ernst Bocker, Wolfgang Kracht, Roland Rupp, Erhard Schellmann, Viktor Trescher, Martin Ullrich, “Preparation of melt-sprayed spherical phenacetin granules.” U.S. Patent US4086346, issued October, 1972.

US4086346
General References
  1. Dubach UC, Rosner B, Sturmer T: An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987) N Engl J Med. 1991 Jan 17;324(3):155-60. [PubMed:1984193 ]
  2. Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. 1967 Jul;12(7):246-50. [PubMed:6036245 ]
  3. TAN GH, RABBINO MD, HOPPER J Jr: IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. Calif Med. 1964 Aug;101:73-7. [PubMed:14180501 ]
  4. Brix AE: Renal papillary necrosis. Toxicol Pathol. 2002 Nov-Dec;30(6):672-4. [PubMed:12512867 ]
External Links
ATC CodesN02BE73N02BE03N02BE53
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (50.3 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9915
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.8257
P-glycoprotein inhibitor INon-inhibitor0.9091
P-glycoprotein inhibitor IINon-inhibitor0.9391
Renal organic cation transporterNon-inhibitor0.889
CYP450 2C9 substrateNon-substrate0.8154
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.5542
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9619
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5441
Ames testAMES toxic0.9108
CarcinogenicityNon-carcinogens0.6859
BiodegradationReady biodegradable0.5762
Rat acute toxicity2.0676 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9679
hERG inhibition (predictor II)Non-inhibitor0.9315
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point137.5 °CPhysProp
water solubility766 mg/L (at 25 °C)SEIDELL,A (1941)
logP1.58NAKAGAWA,Y ET AL. (1992)
logS-2.37ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility1.78 mg/mLALOGPS
logP1.62ALOGPS
logP1.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)14.98ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.13 m3·mol-1ChemAxon
Polarizability19.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.59 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4i-3900000000-a251ba59f8f792deb3e1View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAcetanilides
Alternative Parents
Substituents
  • N-arylamide
  • Acetanilide
  • Phenol ether
  • Alkyl aryl ether
  • Acetamide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Zhang T, Zhu Y, Gunaratna C: Rapid and quantitative determination of metabolites from multiple cytochrome P450 probe substrates by gradient liquid chromatography-electrospray ionization-ion trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 25;780(2):371-9. [PubMed:12401364 ]
  3. Kobayashi K, Nakajima M, Oshima K, Shimada N, Yokoi T, Chiba K: Involvement of CYP2E1 as A low-affinity enzyme in phenacetin O-deethylation in human liver microsomes. Drug Metab Dispos. 1999 Aug;27(8):860-5. [PubMed:10421611 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Possesses phenacetin O-deethylation activity.
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Molecular Weight:
56687.095 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [PubMed:10991954 ]
  2. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23