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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- 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- Withdrawn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Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney).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
Structure for DB03783 (Phenacetin)
- Synonyms
- Acetophenetidin
- Acetophenetidine
- Acetophenetin
- Acetphenetidin
- External IDs
- NSC-7651
- International/Other Brands
- Achrocidin / Codempiral / Commotional / Contradol / Contradouleur
- Categories
- Acetanilides
- Amides
- Analgesics
- Analgesics, Non-Narcotic
- Anilides
- Central Nervous System Agents
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Nervous System
- Peripheral Nervous System Agents
- Sensory System Agents
- 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]
Target Actions Organism UProstaglandin G/H synthase 1 Not Available Human - 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
Drug Interaction Drug group Abiraterone The serum concentration of Phenacetin can be increased when it is combined with Abiraterone. Approved Amiodarone The metabolism of Phenacetin can be decreased when combined with Amiodarone. Approved, Investigational Apalutamide The serum concentration of Phenacetin can be decreased when it is combined with Apalutamide. Approved, Investigational Aprepitant The serum concentration of Phenacetin can be increased when it is combined with Aprepitant. Approved, Investigational Armodafinil The metabolism of Phenacetin can be decreased when combined with Armodafinil. Approved, Investigational Artemether The metabolism of Phenacetin can be decreased when combined with Artemether. Approved Atazanavir The metabolism of Phenacetin can be decreased when combined with Atazanavir. Approved, Investigational Atomoxetine The metabolism of Phenacetin can be decreased when combined with Atomoxetine. Approved Azithromycin The metabolism of Phenacetin can be decreased when combined with Azithromycin. Approved Betaxolol The metabolism of Phenacetin can be decreased when combined with Betaxolol. Approved, Investigational Boceprevir The metabolism of Phenacetin can be decreased when combined with Boceprevir. Approved, Withdrawn Bortezomib The metabolism of Phenacetin can be decreased when combined with Bortezomib. Approved, Investigational Bosentan The serum concentration of Phenacetin can be decreased when it is combined with Bosentan. Approved, Investigational Bupropion The metabolism of Phenacetin can be decreased when combined with Bupropion. Approved Caffeine The metabolism of Phenacetin can be decreased when combined with Caffeine. Approved Capecitabine The metabolism of Phenacetin can be decreased when combined with Capecitabine. Approved, Investigational Carbamazepine The metabolism of Phenacetin can be increased when combined with Carbamazepine. Approved, Investigational Celecoxib The metabolism of Phenacetin can be decreased when combined with Celecoxib. Approved, Investigational Ceritinib The serum concentration of Phenacetin can be increased when it is combined with Ceritinib. Approved Chloramphenicol The metabolism of Phenacetin can be decreased when combined with Chloramphenicol. Approved, Vet Approved Chloroquine The metabolism of Phenacetin can be decreased when combined with Chloroquine. Approved, Investigational, Vet Approved Chlorpromazine The metabolism of Phenacetin can be decreased when combined with Chlorpromazine. Approved, Investigational, Vet Approved Cholecalciferol The metabolism of Phenacetin can be decreased when combined with Cholecalciferol. Approved, Nutraceutical Cimetidine The metabolism of Phenacetin can be decreased when combined with Cimetidine. Approved, Investigational Cinacalcet The metabolism of Phenacetin can be decreased when combined with Cinacalcet. Approved Citalopram The metabolism of Phenacetin can be decreased when combined with Citalopram. Approved Clarithromycin The metabolism of Phenacetin can be decreased when combined with Clarithromycin. Approved Clemastine The metabolism of Phenacetin can be decreased when combined with Clemastine. Approved, Investigational Clobazam The metabolism of Phenacetin can be decreased when combined with Clobazam. Approved, Illicit Clomipramine The metabolism of Phenacetin can be decreased when combined with Clomipramine. Approved, Investigational, Vet Approved Clotrimazole The metabolism of Phenacetin can be decreased when combined with Clotrimazole. Approved, Vet Approved Clozapine The metabolism of Phenacetin can be decreased when combined with Clozapine. Approved Cobicistat The serum concentration of Phenacetin can be increased when it is combined with Cobicistat. Approved Cocaine The metabolism of Phenacetin can be decreased when combined with Cocaine. Approved, Illicit Conivaptan The serum concentration of Conivaptan can be increased when it is combined with Phenacetin. Approved, Investigational Crisaborole The metabolism of Phenacetin can be decreased when combined with Crisaborole. Approved, Investigational Crizotinib The metabolism of Phenacetin can be decreased when combined with Crizotinib. Approved Cyclosporine The metabolism of Phenacetin can be decreased when combined with Cyclosporine. Approved, Investigational, Vet Approved Cyproterone acetate The serum concentration of Phenacetin can be decreased when it is combined with Cyproterone acetate. Approved, Investigational Dabrafenib The serum concentration of Phenacetin can be decreased when it is combined with Dabrafenib. Approved, Investigational Darifenacin The metabolism of Phenacetin can be decreased when combined with Darifenacin. Approved, Investigational Darunavir The serum concentration of Phenacetin can be increased when it is combined with Darunavir. Approved Dasatinib The serum concentration of Phenacetin can be increased when it is combined with Dasatinib. Approved, Investigational Deferasirox The serum concentration of Phenacetin can be decreased when it is combined with Deferasirox. Approved, Investigational Delavirdine The metabolism of Phenacetin can be decreased when combined with Delavirdine. Approved Desipramine The metabolism of Phenacetin can be decreased when combined with Desipramine. Approved, Investigational Dihydroergotamine The metabolism of Phenacetin can be decreased when combined with Dihydroergotamine. Approved, Investigational Diltiazem The metabolism of Phenacetin can be decreased when combined with Diltiazem. Approved, Investigational Diphenhydramine The metabolism of Phenacetin can be decreased when combined with Diphenhydramine. Approved, Investigational Dosulepin The metabolism of Phenacetin can be decreased when combined with Dosulepin. Approved Doxycycline The metabolism of Phenacetin can be decreased when combined with Doxycycline. Approved, Investigational, Vet Approved Dronedarone The metabolism of Phenacetin can be decreased when combined with Dronedarone. Approved Duloxetine The metabolism of Phenacetin can be decreased when combined with Duloxetine. Approved Efavirenz The metabolism of Phenacetin can be decreased when combined with Efavirenz. Approved, Investigational Eliglustat The metabolism of Phenacetin can be decreased when combined with Eliglustat. Approved Enzalutamide The serum concentration of Phenacetin can be decreased when it is combined with Enzalutamide. Approved Erythromycin The metabolism of Phenacetin can be decreased when combined with Erythromycin. Approved, Investigational, Vet Approved Eslicarbazepine acetate The metabolism of Phenacetin can be decreased when combined with Eslicarbazepine acetate. Approved Esomeprazole The metabolism of Phenacetin can be decreased when combined with Esomeprazole. Approved, Investigational Etravirine The metabolism of Phenacetin can be decreased when combined with Etravirine. Approved Floxuridine The metabolism of Phenacetin can be decreased when combined with Floxuridine. Approved Fluconazole The metabolism of Phenacetin can be decreased when combined with Fluconazole. Approved, Investigational Fluorouracil The metabolism of Phenacetin can be decreased when combined with Fluorouracil. Approved Fluoxetine The metabolism of Phenacetin can be decreased when combined with Fluoxetine. Approved, Vet Approved Fluvastatin The metabolism of Phenacetin can be decreased when combined with Fluvastatin. Approved Fluvoxamine The metabolism of Phenacetin can be decreased when combined with Fluvoxamine. Approved, Investigational Fosamprenavir The metabolism of Phenacetin can be decreased when combined with Fosamprenavir. Approved Fosaprepitant The serum concentration of Phenacetin can be increased when it is combined with Fosaprepitant. Approved Fosphenytoin The metabolism of Phenacetin can be increased when combined with Fosphenytoin. Approved, Investigational Fusidic Acid The serum concentration of Phenacetin can be increased when it is combined with Fusidic Acid. Approved, Investigational Gemfibrozil The metabolism of Phenacetin can be decreased when combined with Gemfibrozil. Approved Haloperidol The metabolism of Phenacetin can be decreased when combined with Haloperidol. Approved Idelalisib The metabolism of Phenacetin can be decreased when combined with Idelalisib. Approved Imatinib The metabolism of Phenacetin can be decreased when combined with Imatinib. Approved Imipramine The metabolism of Phenacetin can be decreased when combined with Imipramine. Approved Indinavir The metabolism of Phenacetin can be decreased when combined with Indinavir. Approved Irbesartan The metabolism of Phenacetin can be decreased when combined with Irbesartan. Approved, Investigational Isavuconazole The serum concentration of Phenacetin can be increased when it is combined with Isavuconazole. Approved, Investigational Isavuconazonium The metabolism of Phenacetin can be decreased when combined with Isavuconazonium. Approved, Investigational Isoniazid The metabolism of Phenacetin can be decreased when combined with Isoniazid. Approved, Investigational Isradipine The metabolism of Phenacetin can be decreased when combined with Isradipine. Approved, Investigational Itraconazole The metabolism of Phenacetin can be decreased when combined with Itraconazole. Approved, Investigational Ivacaftor The serum concentration of Phenacetin can be increased when it is combined with Ivacaftor. Approved Ketoconazole The metabolism of Phenacetin can be decreased when combined with Ketoconazole. Approved, Investigational Leflunomide The metabolism of Phenacetin can be decreased when combined with Leflunomide. Approved, Investigational Lidocaine The metabolism of Phenacetin can be decreased when combined with Lidocaine. Approved, Vet Approved Lobeglitazone The metabolism of Phenacetin can be decreased when combined with Lobeglitazone. Approved, Investigational Lopinavir The metabolism of Phenacetin can be decreased when combined with Lopinavir. Approved Lorcaserin The metabolism of Phenacetin can be decreased when combined with Lorcaserin. Approved Lorpiprazole The serum concentration of Phenacetin can be increased when it is combined with Lorpiprazole. Approved Losartan The metabolism of Phenacetin can be decreased when combined with Losartan. Approved Lovastatin The metabolism of Phenacetin can be decreased when combined with Lovastatin. Approved, Investigational Luliconazole The serum concentration of Phenacetin can be increased when it is combined with Luliconazole. Approved Lumacaftor The serum concentration of Phenacetin can be decreased when it is combined with Lumacaftor. Approved Lumefantrine The metabolism of Phenacetin can be decreased when combined with Lumefantrine. Approved Manidipine The metabolism of Phenacetin can be decreased when combined with Manidipine. Approved, Investigational Methadone The metabolism of Phenacetin can be decreased when combined with Methadone. Approved Methotrimeprazine The metabolism of Phenacetin can be decreased when combined with Methotrimeprazine. Approved, Investigational Metoprolol The metabolism of Phenacetin can be decreased when combined with Metoprolol. Approved, Investigational Mexiletine The metabolism of Phenacetin can be decreased when combined with Mexiletine. Approved, Investigational Midostaurin The metabolism of Phenacetin can be decreased when combined with Midostaurin. Approved, Investigational Mifepristone The serum concentration of Phenacetin can be increased when it is combined with Mifepristone. Approved, Investigational Mirabegron The metabolism of Phenacetin can be decreased when combined with Mirabegron. Approved Mitotane The serum concentration of Phenacetin can be decreased when it is combined with Mitotane. Approved Moclobemide The metabolism of Phenacetin can be decreased when combined with Moclobemide. Approved, Investigational Modafinil The metabolism of Phenacetin can be decreased when combined with Modafinil. Approved, Investigational Nefazodone The metabolism of Phenacetin can be decreased when combined with Nefazodone. Approved, Withdrawn Nelfinavir The metabolism of Phenacetin can be decreased when combined with Nelfinavir. Approved Netupitant The serum concentration of Phenacetin can be increased when it is combined with Netupitant. Approved, Investigational Nevirapine The metabolism of Phenacetin can be increased when combined with Nevirapine. Approved Nicardipine The metabolism of Phenacetin can be decreased when combined with Nicardipine. Approved, Investigational Nicotine The metabolism of Phenacetin can be decreased when combined with Nicotine. Approved Nilotinib The metabolism of Phenacetin can be decreased when combined with Nilotinib. Approved, Investigational Olaparib The metabolism of Phenacetin can be decreased when combined with Olaparib. Approved Omeprazole The metabolism of Phenacetin can be decreased when combined with Omeprazole. Approved, Investigational, Vet Approved Osimertinib The serum concentration of Phenacetin can be increased when it is combined with Osimertinib. Approved Palbociclib The serum concentration of Phenacetin can be increased when it is combined with Palbociclib. Approved, Investigational Panobinostat The serum concentration of Phenacetin can be increased when it is combined with Panobinostat. Approved, Investigational Pantoprazole The metabolism of Phenacetin can be decreased when combined with Pantoprazole. Approved Paroxetine The metabolism of Phenacetin can be decreased when combined with Paroxetine. Approved, Investigational Peginterferon alfa-2b The serum concentration of Phenacetin can be decreased when it is combined with Peginterferon alfa-2b. Approved Pentobarbital The metabolism of Phenacetin can be increased when combined with Pentobarbital. Approved, Investigational, Vet Approved Phenobarbital The metabolism of Phenacetin can be increased when combined with Phenobarbital. Approved, Investigational Phenytoin The metabolism of Phenacetin can be increased when combined with Phenytoin. Approved, Vet Approved Pitolisant The serum concentration of Phenacetin can be decreased when it is combined with Pitolisant. Approved, Investigational Posaconazole The metabolism of Phenacetin can be decreased when combined with Posaconazole. Approved, Investigational, Vet Approved Primidone The metabolism of Phenacetin can be increased when combined with Primidone. Approved, Vet Approved Promazine The metabolism of Phenacetin can be decreased when combined with Promazine. Approved, Vet Approved Pyrimethamine The metabolism of Phenacetin can be decreased when combined with Pyrimethamine. Approved, Investigational, Vet Approved Quinidine The metabolism of Phenacetin can be decreased when combined with Quinidine. Approved, Investigational Quinine The metabolism of Phenacetin can be decreased when combined with Quinine. Approved Ranolazine The metabolism of Phenacetin can be decreased when combined with Ranolazine. Approved, Investigational Rifabutin The metabolism of Phenacetin can be increased when combined with Rifabutin. Approved, Investigational Rifampicin The metabolism of Phenacetin can be increased when combined with Rifampicin. Approved Rifapentine The metabolism of Phenacetin can be increased when combined with Rifapentine. Approved, Investigational Ritonavir The metabolism of Phenacetin can be decreased when combined with Ritonavir. Approved, Investigational Rolapitant The metabolism of Phenacetin can be decreased when combined with Rolapitant. Approved, Investigational Ropinirole The metabolism of Phenacetin can be decreased when combined with Ropinirole. Approved, Investigational Rucaparib The metabolism of Phenacetin can be decreased when combined with Rucaparib. Approved, Investigational Saquinavir The metabolism of Phenacetin can be decreased when combined with Saquinavir. Approved, Investigational Sarilumab The therapeutic efficacy of Phenacetin can be decreased when used in combination with Sarilumab. Approved, Investigational Secobarbital The metabolism of Phenacetin can be increased when combined with Secobarbital. Approved, Vet Approved Sertraline The metabolism of Phenacetin can be decreased when combined with Sertraline. Approved Sildenafil The metabolism of Phenacetin can be decreased when combined with Sildenafil. Approved, Investigational Siltuximab The serum concentration of Phenacetin can be decreased when it is combined with Siltuximab. Approved, Investigational Simeprevir The serum concentration of Phenacetin can be increased when it is combined with Simeprevir. Approved Sorafenib The metabolism of Phenacetin can be decreased when combined with Sorafenib. Approved, Investigational St. John's Wort The serum concentration of Phenacetin can be decreased when it is combined with St. John's Wort. Approved, Investigational, Nutraceutical Stiripentol The serum concentration of Phenacetin can be increased when it is combined with Stiripentol. Approved Sulfadiazine The metabolism of Phenacetin can be decreased when combined with Sulfadiazine. Approved, Investigational, Vet Approved Sulfamethoxazole The metabolism of Phenacetin can be decreased when combined with Sulfamethoxazole. Approved Sulfisoxazole The metabolism of Phenacetin can be decreased when combined with Sulfisoxazole. Approved, Vet Approved Telaprevir The metabolism of Phenacetin can be decreased when combined with Telaprevir. Approved, Withdrawn Telithromycin The metabolism of Phenacetin can be decreased when combined with Telithromycin. Approved Tenofovir disoproxil The metabolism of Phenacetin can be decreased when combined with Tenofovir disoproxil. Approved, Investigational Terbinafine The metabolism of Phenacetin can be decreased when combined with Terbinafine. Approved, Investigational, Vet Approved Teriflunomide The serum concentration of Phenacetin can be decreased when it is combined with Teriflunomide. Approved Theophylline The metabolism of Phenacetin can be decreased when combined with Theophylline. Approved Thioridazine The metabolism of Phenacetin can be decreased when combined with Thioridazine. Approved, Withdrawn Ticagrelor The metabolism of Phenacetin can be decreased when combined with Ticagrelor. Approved Ticlopidine The metabolism of Phenacetin can be decreased when combined with Ticlopidine. Approved Tipranavir The metabolism of Phenacetin can be decreased when combined with Tipranavir. Approved, Investigational Tocilizumab The serum concentration of Phenacetin can be decreased when it is combined with Tocilizumab. Approved Tolbutamide The metabolism of Phenacetin can be decreased when combined with Tolbutamide. Approved, Investigational Topiramate The metabolism of Phenacetin can be decreased when combined with Topiramate. Approved Topiroxostat The metabolism of Phenacetin can be decreased when combined with Topiroxostat. Approved, Investigational Tranylcypromine The metabolism of Phenacetin can be decreased when combined with Tranylcypromine. Approved, Investigational Trimethoprim The metabolism of Phenacetin can be decreased when combined with Trimethoprim. Approved, Vet Approved Valproic Acid The metabolism of Phenacetin can be decreased when combined with Valproic Acid. Approved, Investigational Valsartan The metabolism of Phenacetin can be decreased when combined with Valsartan. Approved, Investigational Vemurafenib The serum concentration of Phenacetin can be increased when it is combined with Vemurafenib. Approved Venlafaxine The metabolism of Phenacetin can be decreased when combined with Venlafaxine. Approved Verapamil The metabolism of Phenacetin can be decreased when combined with Verapamil. Approved Voriconazole The metabolism of Phenacetin can be decreased when combined with Voriconazole. Approved, Investigational Zafirlukast The metabolism of Phenacetin can be decreased when combined with Zafirlukast. Approved, Investigational Ziprasidone The metabolism of Phenacetin can be decreased when combined with Ziprasidone. Approved Zucapsaicin The metabolism of Phenacetin can be decreased when combined with Zucapsaicin. Approved, Investigational - 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
- 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]
- Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. 1967 Jul;12(7):246-50. [PubMed:6036245]
- 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]
- Brix AE: Renal papillary necrosis. Toxicol Pathol. 2002 Nov-Dec;30(6):672-4. [PubMed:12512867]
- External Links
- ATC Codes
- N02BE73 — Phenacetin, combinations with psycholepticsN02BE03 — PhenacetinN02BE53 — Phenacetin, combinations excl. psycholeptics
- PDB Entries
- 3ebs
- MSDS
- Download (50.3 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 137.5 °C PhysProp water solubility 766 mg/L (at 25 °C) SEIDELL,A (1941) logP 1.58 NAKAGAWA,Y ET AL. (1992) logS -2.37 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 1.78 mg/mL ALOGPS logP 1.62 ALOGPS logP 1.41 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 14.98 ChemAxon pKa (Strongest Basic) -4.2 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 38.33 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 52.13 m3·mol-1 ChemAxon Polarizability 19.82 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9915 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.8257 P-glycoprotein inhibitor I Non-inhibitor 0.9091 P-glycoprotein inhibitor II Non-inhibitor 0.9391 Renal organic cation transporter Non-inhibitor 0.889 CYP450 2C9 substrate Non-substrate 0.8154 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.5542 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9619 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5441 Ames test AMES toxic 0.9108 Carcinogenicity Non-carcinogens 0.6859 Biodegradation Ready biodegradable 0.5762 Rat acute toxicity 2.0676 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9679 hERG inhibition (predictor II) Non-inhibitor 0.9315
Spectra
- Mass Spec (NIST)
- Download (8.59 KB)
- Spectra
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
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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]
- 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 March 02, 2018 02:44