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Showing Compound Demethylated antipyrine (FDB023854)

Record Information
Version1.0
Creation date2011-09-21 00:35:49 UTC
Update date2015-07-21 06:57:54 UTC
Primary IDFDB023854
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDemethylated antipyrine
DescriptionDemethylated antipyrine is a novel potent free radical scavenger that has been clinically used to reduce the neuronal damage following ischemic stroke. Demethylated antipyrine exerts neuroprotective effects by inhibiting endothelial injury and by ameliorating neuronal damage in brain ischemia. Demethylated antipyrine provides the desirable features of NOS: it increases eNOS (beneficial NOS for rescuing ischemic stroke) and decreases nNOS and iNOS (detrimental NOS). Post- reperfusion brain edema and hemorrhagic events induced by thrombolytic therapy may be reduced by demethylated antipyrine pretreatment. Increased productions of superoxide and NO in the brain after reperfusion and a concomitant surge in oxygen free radicals with increased NO during recirculation lead to formation of peroxynitrite, a super potent radical. Demethylated antipyrine, which inhibits oxidation and enhances NO production derived from increased eNOS expression, may improve and conserve cerebral blood flow without peroxynitrite generation during reperfusion. Clinical experience with demethylated antipyrine suggests that this drug has a wide therapeutic time window. Demethylated antipyrine can exert a wide range of inhibitory effects on water-soluble and lipid soluble peroxyl radical-induced peroxidation systems, and appears to display combined properties of both, vitamin C and E. Demethylated antipyrine can scavenge not only hydroxyl radicals but also other free radicals, although it has no major effect on superoxide anion radicals. Demethylated antipyrine apparently traps hydroxyl radicals and inhibits OH-dependent lipid peroxidation or tyrosine nitration induced by peroxynitrite (ONOO-). Lipid peroxidation starts with lipid radical (L) production after free radical-mediated extraction of proton from unsaturated fatty acid. Subsequently lipid peroxyl radical (LOO) is generated by addition of oxygen atom, and a further L is produced by LOO-mediated extraction of proton from another unsaturated fatty acid. Demethylated antipyrine can inhibit lipid peroxidation by scavenging not only hydroxyl radicals but also other free radicals including LOO. Under physiological conditions, 50% of demethylated antipyrine is present as an anion form, and electrons released from demethylated antipyrine anion exert radical scavenging. Subsequently, demethylated antipyrine radicals are generated. They react readily with oxygen atoms, and form peroxyl radical of demethylated antipyrine, and eventually 2-oxo-3-(phenylhydrazone)- butanoic acid (OPB). (PMID: 16834755, CNS Drug Rev. 2006 Spring;12(1):9-20.) [HMDB]
CAS Number89-25-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility19.3 g/LALOGPS
logP0.59ALOGPS
logP1.28ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)8.27ChemAxon
pKa (Strongest Basic)1.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.14 m³·mol⁻¹ChemAxon
Polarizability18.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H10N2O
IUPAC name5-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
InChI IdentifierInChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-7,11H,1H3
InChI KeyKZQYIMCESJLPQH-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(=O)N(N1)C1=CC=CC=C1
Average Molecular Weight174.1992
Monoisotopic Molecular Weight174.079312952
Classification
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
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDemethylated antipyrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4900000000-e7fde844e072d094e7bfSpectrum
Predicted GC-MSDemethylated antipyrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDemethylated antipyrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-ccca975ba1e597027ed52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-96da0ec122d8a84034862017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9500000000-905aac7834f5ebcbec592017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-8e7cd9ae2599cec8be882017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-dbe1b04ba8ec0bb7b01a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054k-6900000000-e3078766e74d43ea5dce2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-99e013a33d61f5b2babb2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-96887c840d6d9faeba922021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-a5215b963ef8a7e941172021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-6c988551b42e630dedc72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xr-9600000000-0d26a32aab574f87a2822021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9100000000-89d891f53ac7bcc51cdb2021-09-25View Spectrum
NMRNot Available
ChemSpider ID63516
ChEMBL IDNot Available
KEGG Compound IDC13008
Pubchem Compound ID70335
Pubchem Substance IDNot Available
ChEBI ID31530
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06240
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2299979
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference