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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:43 UTC
HMDB IDHMDB0015493
Secondary Accession Numbers
  • HMDB15493
Metabolite Identification
Common NameAminophenazone
DescriptionAminophenazone, also known as aminofenazona or aminopyrine, belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. Aminophenazone is a drug which is used formerly widely used as an antipyretic and analgesic in rheumatism, neuritis, and common colds. currently used to measure total body water. A breath test with 13C-labeled Aminophenazone has been used as a non-invasive measure of cytochrome P-450 metabolic activity in liver function tests. It is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of agranulocytosis. Aminophenazone is a strong basic compound (based on its pKa). Aminophenazone is a potentially toxic compound. Aminophenazone is only found in individuals that have used or taken this drug. In biomedical applications, radiolabelled (13C-labeled) aminophenazone has been used in breath tests to measure the cytochrome P-450 metabolic activity in liver function tests. Aminophenazone is a pyrazolone with analgesic, anti-inflammatory, and antipyretic properties that carries a risk of agranulocytosis.
Structure
Data?1582753303
Synonyms
ValueSource
(Dimethylamino)phenazoneChEBI
1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazoloneChEBI
1-Phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazoloneChEBI
1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-oneChEBI
2,3-Dimethyl-4-dimethylamino-1-phenyl-5-pyrazoloneChEBI
3-Keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazoleChEBI
4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-oneChEBI
4-(Dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-oneChEBI
4-(Dimethylamino)antipyrineChEBI
4-Dimethylamino-1-phenyl-2,3-dimethylpyrazoloneChEBI
4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-oneChEBI
4-Dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazoloneChEBI
4-DimethylaminoantipyrineChEBI
4-DimethylaminophenazoneChEBI
AminofenazonaChEBI
AminofenazoneChEBI
AminophenazonChEBI
AminophenazonumChEBI
AminopyrineChEBI
DimethylaminoantipyrineChEBI
DimethylaminoazopheneChEBI
DimethylaminophenazonChEBI
DimethylaminophenazoneChEBI
DimethylaminophenyldimethylpyrazoloneChEBI
DipyrineChEBI
AmidophenHMDB
AmidophenazonHMDB
Aminophenazone berlin-chemie brandHMDB
Berlin-chemie brand OF aminophenazoneHMDB
Dimethyl-N-aminoantipyrineHMDB
Berlin chemie brand OF aminophenazoneHMDB
Dimethyl N aminoantipyrineHMDB
EufibronHMDB
AmidazophenHMDB
AmidopyrineHMDB
Chemical FormulaC13H17N3O
Average Molecular Weight231.2936
Monoisotopic Molecular Weight231.137162181
IUPAC Name4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
Traditional Nameaminophenazone
CAS Registry Number58-15-1
SMILES
CN(C)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1
InChI Identifier
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
InChI KeyRMMXTBMQSGEXHJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles 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
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Monocyclic benzene moiety
  • Pyrazolinone
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Tertiary amine
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point134.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility22.5 g/LNot Available
LogP1.00HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility22.5 g/LALOGPS
logP0.94ALOGPS
logP1.15ChemAxon
logS-1ALOGPS
pKa (Strongest Basic)3.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.79 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.11 m³·mol⁻¹ChemAxon
Polarizability25.87 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053s-9250000000-c3308b81b44067a47f7eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9100000000-40e7051a3536ae680d1aSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-053s-9250000000-c3308b81b44067a47f7eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9100000000-40e7051a3536ae680d1aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0159-4970000000-8cb60fc41366bf1c7f80Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dr-1900000000-49de43a88698c1df262bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0190000000-d7bfbe39ac8d423c5cfdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03e9-4940000000-243b2713c256a2ab8b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dj-9700000000-3ef4e69c38623bfd699fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06r2-9300000000-762e3df6382a5e2052a3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0592-9100000000-b9c175ecf48888c0267aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-9100000000-9fa64e7904c1473d9d32Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0290000000-27bac0f1542859b73671Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03e9-4940000000-a4c3f3e347d595ad803eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dj-9700000000-ac217c24c44682808465Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06xt-9300000000-f8259f5a45014efc58eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-052b-9100000000-307762c9c387df2fcbf4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4j-9100000000-3c5267564fda210cc134Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03dr-1900000000-ab951ea405c6154ef630Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0090000000-2527cae3cd95916624e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-3910000000-f7ee26001f3fbe463baeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01vk-9400000000-243fad64356c2d2c4864Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0592-9100000000-bbc78ee3e540bd560a88Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0aba-9000000000-1c4e7d6f8c8bbdc08335Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-0896fba0b89cb8cb6ff5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2390000000-eaa608d1cc64b37d59dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9100000000-db54dcd1f4d6da575bf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3920000000-00258f4a6df2920817ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f8i-5790000000-dd0fbe214d13e5ebfde8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00l6-9300000000-18386f94d530fc45afc1Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01424 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01424 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01424
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5787
KEGG Compound IDC07539
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAminophenazone
METLIN IDNot Available
PubChem Compound6009
PDB IDNot Available
ChEBI ID160246
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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 ]