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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:04:46 UTC
Update Date2023-02-21 17:30:16 UTC
HMDB IDHMDB0060878
Secondary Accession Numbers
  • HMDB60878
Metabolite Identification
Common Name4-Hydroxyantipyrine
Description4-Hydroxyantipyrine, a major metabolite of the drug antipyrine. Antypyrene is an analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver (PMID: 6121894 , 8735513 ). In man, 30–40% of an antipyrine dose is typically oxidized to 4-hydroxyantipyrine. In addition to its use for monitoring drug metabolism, 4-hydroxyantipyrine has also been used as a drug biodistribution promoter (PMID: 11767111 ). 4-Hydroxyantipyrine is only found in individuals who have taken or received the drug antipyrine.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H12N2O2
Average Molecular Weight204.2252
Monoisotopic Molecular Weight204.089877638
IUPAC Name4-hydroxy-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
Traditional Name4-hydroxy-1,5-dimethyl-2-phenylpyrazol-3-one
CAS Registry NumberNot Available
SMILES
CN1N(C(=O)C(O)=C1C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H12N2O2/c1-8-10(14)11(15)13(12(8)2)9-6-4-3-5-7-9/h3-7,14H,1-2H3
InChI KeySKVPTPMWXJSBTF-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
  • Monocyclic benzene moiety
  • Pyrazolinone
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available141.435http://allccs.zhulab.cn/database/detail?ID=AllCCS00001099
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound98889
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bottcher J, Bassmann H, Schuppel R: Quantitation and urinary pattern of 4,4'-dihydroxy-antipyrine, 4-hydroxy-antipyrine and 3-hydroxymethyl-antipyrine, as main metabolites of antipyrine in man and rat. J Pharm Pharmacol. 1982 Mar;34(3):168-75. doi: 10.1111/j.2042-7158.1982.tb04215.x. [PubMed:6121894 ]
  2. Janus K, Suszycka J: Effect of age on the pharmacokinetics of antipyrine in calves. Res Vet Sci. 1996 May;60(3):234-7. doi: 10.1016/s0034-5288(96)90045-4. [PubMed:8735513 ]
  3. Ohkawa Y, Kiyohara Y, Asoh T, Maeda H, Kurumi M, Sasaki K, Kurosaki Y, Matsumura M, Nakayama T: Application of 4-hydroxyantipyrine and acetaminophen O-sulfate as biodistribution promoter. Biol Pharm Bull. 2001 Dec;24(12):1404-10. doi: 10.1248/bpb.24.1404. [PubMed:11767111 ]