Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2013-07-09 16:04:46 UTC |
---|
Update Date | 2023-02-21 17:30:16 UTC |
---|
HMDB ID | HMDB0060878 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | 4-Hydroxyantipyrine |
---|
Description | 4-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 | CN1N(C(=O)C(O)=C1C)C1=CC=CC=C1 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 |
---|
Synonyms | Not Available |
---|
Chemical Formula | C11H12N2O2 |
---|
Average Molecular Weight | 204.2252 |
---|
Monoisotopic Molecular Weight | 204.089877638 |
---|
IUPAC Name | 4-hydroxy-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one |
---|
Traditional Name | 4-hydroxy-1,5-dimethyl-2-phenylpyrazol-3-one |
---|
CAS Registry Number | Not 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 Key | SKVPTPMWXJSBTF-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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Azoles |
---|
Sub Class | Pyrazoles |
---|
Direct Parent | Phenylpyrazoles |
---|
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 Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Experimental Collision Cross Sections |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyantipyrine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fbi-3910000000-c98f07a419260f2ebee5 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyantipyrine GC-MS (1 TMS) - 70eV, Positive | splash10-0229-6970000000-4157d8ad16409897e729 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 4-Hydroxyantipyrine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 10V, Positive-QTOF | splash10-0a4i-0190000000-292149064e355d5990d2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 20V, Positive-QTOF | splash10-0a6r-9730000000-b226bb7edf212df27cf6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 40V, Positive-QTOF | splash10-00di-3900000000-4bd99b951eeadc20b6a9 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 10V, Negative-QTOF | splash10-0udi-1390000000-af26936060dbf3af58ff | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 20V, Negative-QTOF | splash10-0uk9-1910000000-efa28afb9a3d7ad21933 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 40V, Negative-QTOF | splash10-0006-9300000000-75bff330553ba4a233d1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 10V, Positive-QTOF | splash10-0a4i-0090000000-82053d3e7735d22e65cf | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 20V, Positive-QTOF | splash10-0a4i-3790000000-62d9b91b90f6c4a97eec | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 40V, Positive-QTOF | splash10-004i-9000000000-586628bded880a48b8d8 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 10V, Negative-QTOF | splash10-0udi-0090000000-9b41106fc25a17d1b2b2 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 20V, Negative-QTOF | splash10-00kf-9510000000-5e0092c6cf3b99537c96 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 4-Hydroxyantipyrine 40V, Negative-QTOF | splash10-0006-9300000000-1c735bb91571d85a98be | 2021-10-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
---|
Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
|
---|
General References | - 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 ]
- 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 ]
- 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 ]
|
---|