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Identification
NameAminophenazone
Accession NumberDB01424
TypeSmall Molecule
GroupsApproved, Withdrawn
DescriptionA pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [PubChem]
Structure
Thumb
Synonyms
(Dimethylamino)phenazone
1-Phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazolone
1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one
1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone
2,3-Dimethyl-4-dimethylamino-1-phenyl-5-pyrazolone
3-Keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazole
4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
4-(Dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
4-(Dimethylamino)antipyrine
4-Dimethylamino-1-phenyl-2,3-dimethylpyrazolone
4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
4-Dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone
4-Dimethylaminoantipyrine
4-Dimethylaminophenazone
Aminofenazona
Aminofenazone
Aminophenazon
Aminophenazonum
Aminopyrine
Dimethylaminoantipyrine
Dimethylaminoazophene
Dimethylaminophenazon
Dimethylaminophenazone
Dimethylaminophenyldimethylpyrazolone
Dipyrine
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 BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII01704YP3MO
CAS number58-15-1
WeightAverage: 231.2936
Monoisotopic: 231.137162181
Chemical FormulaC13H17N3O
InChI KeyRMMXTBMQSGEXHJ-UHFFFAOYSA-N
InChI
InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3
IUPAC Name
4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
SMILES
CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1
Pharmacology
IndicationFormerly widely used as an antipyretic and analgesic in rheumatism, neuritis, and common colds. Currently used to measure total body water.
Structured Indications Not Available
PharmacodynamicsAminophenazone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. [Wikipedia]
Mechanism of actionAminophenazone is metabolized very slowly by normal newborn babies. In older infants, a higher amount of exhaled 13-CO2 is observed.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Aminophenazone
N-DesmethylaminopyrineDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityCan cause life-threatening agranulocytosis.
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 Aminophenazone can be increased when it is combined with Abiraterone.Approved
AmiodaroneThe metabolism of Aminophenazone can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Aminophenazone can be increased when it is combined with Aprepitant.Approved, Investigational
ArmodafinilThe metabolism of Aminophenazone can be decreased when combined with Armodafinil.Approved, Investigational
ArtemetherThe metabolism of Aminophenazone can be decreased when combined with Artemether.Approved
AtazanavirThe metabolism of Aminophenazone can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Aminophenazone can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Aminophenazone can be decreased when combined with Azithromycin.Approved
BetaxololThe metabolism of Aminophenazone can be decreased when combined with Betaxolol.Approved
BexaroteneThe serum concentration of Aminophenazone can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Aminophenazone can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Aminophenazone can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Aminophenazone can be decreased when it is combined with Bosentan.Approved, Investigational
BupropionThe metabolism of Aminophenazone can be decreased when combined with Bupropion.Approved
CaffeineThe metabolism of Aminophenazone can be decreased when combined with Caffeine.Approved
CapecitabineThe metabolism of Aminophenazone can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Aminophenazone can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Aminophenazone can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Aminophenazone can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Aminophenazone can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineThe metabolism of Aminophenazone can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Aminophenazone can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Aminophenazone can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Aminophenazone.Approved
CimetidineThe metabolism of Aminophenazone can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Aminophenazone can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Aminophenazone can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Aminophenazone can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Aminophenazone can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Aminophenazone can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Aminophenazone can be decreased when combined with Clomipramine.Approved, Vet Approved
ClopidogrelThe metabolism of Aminophenazone can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Aminophenazone can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Aminophenazone can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Aminophenazone can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Aminophenazone can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Aminophenazone can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Aminophenazone can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Aminophenazone can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Aminophenazone can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Aminophenazone can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe metabolism of Aminophenazone can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Aminophenazone can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Aminophenazone can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Aminophenazone can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Aminophenazone can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Aminophenazone can be decreased when combined with Desipramine.Approved
DexamethasoneThe serum concentration of Aminophenazone can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DihydroergotamineThe metabolism of Aminophenazone can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Aminophenazone can be decreased when combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Aminophenazone can be decreased when combined with Diphenhydramine.Approved
DoxycyclineThe metabolism of Aminophenazone can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Aminophenazone can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Aminophenazone can be decreased when combined with Duloxetine.Approved
EfavirenzThe serum concentration of Aminophenazone can be decreased when it is combined with Efavirenz.Approved, Investigational
EliglustatThe metabolism of Aminophenazone can be decreased when combined with Eliglustat.Approved
EnzalutamideThe serum concentration of Aminophenazone can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Aminophenazone can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Aminophenazone can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Aminophenazone can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe serum concentration of Aminophenazone can be decreased when it is combined with Etravirine.Approved
FelodipineThe metabolism of Aminophenazone can be decreased when combined with Felodipine.Approved, Investigational
FloxuridineThe metabolism of Aminophenazone can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Aminophenazone can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Aminophenazone can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Aminophenazone can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe metabolism of Aminophenazone can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Aminophenazone can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Aminophenazone can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Aminophenazone can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Aminophenazone can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Aminophenazone can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe metabolism of Aminophenazone can be decreased when combined with Gemfibrozil.Approved
HaloperidolThe metabolism of Aminophenazone can be decreased when combined with Haloperidol.Approved
IdelalisibThe serum concentration of Aminophenazone can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Aminophenazone can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Aminophenazone can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Aminophenazone can be decreased when combined with Indinavir.Approved
IrbesartanThe metabolism of Aminophenazone can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Aminophenazone can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Aminophenazone can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Aminophenazone can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Aminophenazone can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Aminophenazone can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Aminophenazone can be decreased when combined with Ketoconazole.Approved, Investigational
LapatinibThe metabolism of Aminophenazone can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideThe metabolism of Aminophenazone can be decreased when combined with Leflunomide.Approved, Investigational
LidocaineThe metabolism of Aminophenazone can be decreased when combined with Lidocaine.Approved, Vet Approved
LopinavirThe metabolism of Aminophenazone can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Aminophenazone can be decreased when combined with Lorcaserin.Approved
LosartanThe metabolism of Aminophenazone can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Aminophenazone can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Aminophenazone can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Aminophenazone can be increased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Aminophenazone can be decreased when combined with Lumefantrine.Approved
MethadoneThe metabolism of Aminophenazone can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Aminophenazone can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe metabolism of Aminophenazone can be decreased when combined with Metoprolol.Approved, Investigational
MexiletineThe metabolism of Aminophenazone can be decreased when combined with Mexiletine.Approved
MifepristoneThe serum concentration of Aminophenazone can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe metabolism of Aminophenazone can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Aminophenazone can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Aminophenazone can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of Aminophenazone can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Aminophenazone can be decreased when it is combined with Nafcillin.Approved
NefazodoneThe metabolism of Aminophenazone can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Aminophenazone can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Aminophenazone can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Aminophenazone can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Aminophenazone can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Aminophenazone can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Aminophenazone can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Aminophenazone can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Aminophenazone can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Aminophenazone can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Aminophenazone can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Aminophenazone can be decreased when combined with Pantoprazole.Approved
ParoxetineThe metabolism of Aminophenazone can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Aminophenazone can be decreased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Aminophenazone can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Aminophenazone can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Aminophenazone can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe metabolism of Aminophenazone can be decreased when combined with Pioglitazone.Approved, Investigational
PosaconazoleThe metabolism of Aminophenazone can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimidoneThe metabolism of Aminophenazone can be increased when combined with Primidone.Approved, Vet Approved
PromazineThe metabolism of Aminophenazone can be decreased when combined with Promazine.Approved, Vet Approved
PyrimethamineThe metabolism of Aminophenazone can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinidineThe metabolism of Aminophenazone can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Aminophenazone can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Aminophenazone can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe metabolism of Aminophenazone can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Aminophenazone can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Aminophenazone can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Aminophenazone can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Aminophenazone can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Aminophenazone can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Aminophenazone can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneThe metabolism of Aminophenazone can be decreased when combined with Rosiglitazone.Approved, Investigational
SaquinavirThe metabolism of Aminophenazone can be decreased when combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Aminophenazone can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Aminophenazone can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Aminophenazone can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Aminophenazone can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Aminophenazone can be increased when it is combined with Simeprevir.Approved
SorafenibThe metabolism of Aminophenazone can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Aminophenazone can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Aminophenazone can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Aminophenazone can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Aminophenazone can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Aminophenazone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TamoxifenThe metabolism of Aminophenazone can be decreased when combined with Tamoxifen.Approved
TelaprevirThe metabolism of Aminophenazone can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Aminophenazone can be decreased when combined with Telithromycin.Approved
TenofovirThe metabolism of Aminophenazone can be decreased when combined with Tenofovir.Approved, Investigational
TerbinafineThe metabolism of Aminophenazone can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TeriflunomideThe serum concentration of Aminophenazone can be decreased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Aminophenazone can be decreased when combined with Theophylline.Approved
ThioridazineThe metabolism of Aminophenazone can be decreased when combined with Thioridazine.Approved
TicagrelorThe metabolism of Aminophenazone can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Aminophenazone can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Aminophenazone can be decreased when combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Aminophenazone can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Aminophenazone can be decreased when combined with Tolbutamide.Approved
TopiramateThe metabolism of Aminophenazone can be decreased when combined with Topiramate.Approved
TranylcypromineThe metabolism of Aminophenazone can be decreased when combined with Tranylcypromine.Approved
TrimethoprimThe metabolism of Aminophenazone can be decreased when combined with Trimethoprim.Approved, Vet Approved
Valproic AcidThe metabolism of Aminophenazone can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Aminophenazone can be decreased when combined with Valsartan.Approved, Investigational
VemurafenibThe serum concentration of Aminophenazone can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Aminophenazone can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Aminophenazone can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Aminophenazone can be decreased when combined with Voriconazole.Approved, Investigational
ZafirlukastThe metabolism of Aminophenazone can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Aminophenazone can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Rating D, Langhans CD: Breath tests: concepts, applications and limitations. Eur J Pediatr. 1997 Aug;156 Suppl 1:S18-23. [PubMed:9266210 ]
External Links
ATC CodesN02BB53N02BB73N02BB03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9845
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.7772
P-glycoprotein inhibitor INon-inhibitor0.7283
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.8779
CYP450 2C9 substrateNon-substrate0.7595
CYP450 2D6 substrateSubstrate0.8154
CYP450 3A4 substrateSubstrate0.7049
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9337
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.957
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6183
Ames testAMES toxic0.6234
CarcinogenicityNon-carcinogens0.835
BiodegradationNot ready biodegradable0.9871
Rat acute toxicity2.8773 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9691
hERG inhibition (predictor II)Non-inhibitor0.7392
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 point134.5 °CPhysProp
water solubility5.44E+004 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.00HANSCH,C ET AL. (1995)
logS-0.63ADME Research, USCD
Caco2 permeability-4.44ADME Research, USCD
pKa5SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility22.5 mg/mLALOGPS
logP0.94ALOGPS
logP1.15ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)3.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.79 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.11 m3·mol-1ChemAxon
Polarizability25.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.35 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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Dialkylarylamine
  • Benzenoid
  • Pyrazolinone
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Tertiary amine
  • Lactam
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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:
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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
substrateinhibitor
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular Weight:
55710.075 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 17-alpha-monooxygenase activity
Specific Function:
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:
CYP17A1
Uniprot ID:
P05093
Molecular Weight:
57369.995 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:
Oxygen binding
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:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 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. 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 July 24, 2007 05:44 / Updated on August 17, 2016 12:23