Identification

Name
Phenacetin
Accession Number
DB03783  (EXPT03306, DB08243)
Type
Small Molecule
Groups
Withdrawn
Description

Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney).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 IDs
NSC-7651
International/Other Brands
Achrocidin / Codempiral / Commotional / Contradol / Contradouleur
Categories
UNII
ER0CTH01H9
CAS number
62-44-2
Weight
Average: 179.2157
Monoisotopic: 179.094628665
Chemical Formula
C10H13NO2
InChI Key
CPJSUEIXXCENMM-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

Indication

Used principally as an analgesic.

Structured Indications
Not Available
Pharmacodynamics

Phenacetin 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 action

Phenacetin'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]

TargetActionsOrganism
UProstaglandin G/H synthase 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Metabolised in the body to paracetamol.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Acute oral toxicity (LD50): 866 mg/kg [Mouse].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not 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
BoceprevirThe metabolism of Phenacetin can be decreased when combined with Boceprevir.Approved, Withdrawn
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
CrisaboroleThe metabolism of Phenacetin can be decreased when combined with Crisaborole.Approved
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
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
DosulepinThe metabolism of Phenacetin can be decreased when combined with Dosulepin.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 metabolism of Phenacetin can be decreased when 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 metabolism of Phenacetin can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Phenacetin can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe metabolism of Phenacetin can be decreased when 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
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
LobeglitazoneThe metabolism of Phenacetin can be decreased when combined with Lobeglitazone.Approved, Investigational
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
ManidipineThe metabolism of Phenacetin can be decreased when combined with Manidipine.Approved, Investigational
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
MidostaurinThe metabolism of Phenacetin can be decreased when combined with Midostaurin.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 metabolism of Phenacetin can be decreased when combined with Modafinil.Approved, Investigational
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.Investigational, 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, Withdrawn
TelithromycinThe metabolism of Phenacetin can be decreased when combined with Telithromycin.Approved
Tenofovir disoproxilThe metabolism of Phenacetin can be decreased when combined with Tenofovir disoproxil.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, Withdrawn
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
TopiroxostatThe metabolism of Phenacetin can be decreased when combined with Topiroxostat.Approved, Investigational
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
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
ZucapsaicinThe metabolism of Phenacetin can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not 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
KEGG Drug
D00569
KEGG Compound
C07591
PubChem Compound
4754
PubChem Substance
46507394
ChemSpider
4590
BindingDB
50420191
ChEBI
8050
ChEMBL
CHEMBL16073
Therapeutic Targets Database
DNC001117
PharmGKB
PA450897
HET
N4E
Wikipedia
Phenacetin
ATC Codes
N02BE73 — Phenacetin, combinations with psycholepticsN02BE53 — Phenacetin, combinations excl. psycholepticsN02BE03 — Phenacetin
PDB Entries
3ebs
MSDS
Download (50.3 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)137.5 °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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Download (8.59 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - CI-BGC-MSsplash10-001i-0900000000-335c6f93c6c61172faca
Mass Spectrum (Electron Ionization)MSsplash10-0a4i-3900000000-a251ba59f8f792deb3e1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-ff1bc2f7f827dd1711f6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01qi-0900000000-8d7f58b56528e6f12b90
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0900000000-632d2f940d3bf1e4b090
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-2900000000-a8b75ec081cf2f9bd170
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0c03-2900000000-115f1b03c65a7dc2e1e9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0900000000-375522dc595b7e227b62
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-6900100000-e5425770c8b511b991fa
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as acetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Acetanilides
Alternative Parents
N-acetylarylamines / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Acetamides / Secondary carboxylic acid amides / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Acetanilide / N-acetylarylamine / Phenoxy compound / Phenol ether / N-arylamide / Alkyl aryl ether / Acetamide / Carboxamide group / Secondary carboxylic acid amide / Ether
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic ether, acetamides (CHEBI:8050)

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 gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
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-s...
Gene Name
CYP2A13
Uniprot ID
Q16696
Uniprot Name
Cytochrome P450 2A13
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. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
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 un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
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 ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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 ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
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]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:18