4-hydroxyantipyrine, also known as 4-OH-antipyrine, is a metabolite of antipyrine, a non-steroidal anti-inflammatory drug. It is formed in the liver by the enzyme cytochrome P450. 4-OH-antipyrine is a potent inhibitor of the enzyme aldehyde oxidase, which is involved in the metabolism of various drugs and other compounds. It is also known to have antioxidant and anti-inflammatory properties. 4-hydroxyantipyrine is studied for its potential therapeutic applications, including the treatment of inflammatory diseases, cancer, and neurodegenerative disorders. It is also used as a probe for the study of cytochrome P450 activity and aldehyde oxidase inhibition.'
4-hydroxyantipyrine: metabolite of antipyrine; structure in third source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 98889 |
| CHEMBL ID | 1526434 |
| CHEBI ID | 94641 |
| SCHEMBL ID | 151171 |
| MeSH ID | M0051489 |
| Synonym |
|---|
| 4-hydroxy-1,5-dimethyl-2-phenyl-1,2-dihydro-3h-pyrazol-3-one |
| MLS002154180 |
| smr001233473 |
| BRD-K49759007-001-03-6 |
| 1672-63-5 |
| 3h-pyrazol-3-one,2-dihydro-4-hydroxy-1,5-dimethyl-2-phenyl- |
| nsc174055 |
| nsc-174055 |
| antipyrine, 4-hydroxy |
| PRESTWICK_270 , |
| NCGC00016592-01 |
| cas-1672-63-5 |
| PRESTWICK2_000030 |
| NCGC00179659-01 |
| BPBIO1_000109 |
| PRESTWICK3_000030 |
| BSPBIO_000099 |
| 4-hydroxyantipyrine, 99% |
| PRESTWICK0_000030 |
| SPBIO_002020 |
| PRESTWICK1_000030 |
| 4-hydroxyantipyrine |
| 4-hydroxy-1,5-dimethyl-2-phenylpyrazol-3-one |
| HMS1568E21 |
| HMS2095E21 |
| unii-dpz41nv570 |
| dpz41nv570 , |
| nsc 174055 |
| 3h-pyrazol-3-one, 1,2-dihydro-4-hydroxy-1,5-dimethyl-2-phenyl- |
| HMS2230K12 |
| NCGC00016592-02 |
| FT-0633751 |
| HMS3370O19 |
| CCG-214538 |
| AKOS022181399 |
| SCHEMBL151171 |
| 1,2-dihydro-4-hydroxy-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one |
| 4-hydroxyantipyrene |
| CHEMBL1526434 |
| DTXSID70168242 |
| STL454169 |
| 4-hydroxyantipyrine, analytical standard |
| SR-01000841217-2 |
| sr-01000841217 |
| CHEBI:94641 |
| J-010349 |
| HMS3712E21 |
| antipyrine, 4-hydroxy- |
| 4-hydroxy-1,5-dimethyl-3-oxo-2-phenyl pyrazoline |
| 4-hydroxyphenazone |
| 4-hydroxy-1,5-dimethyl-2-phenyl-1h-pyrazol-3(2h)-one |
| 4-hydroxy-1,5-dimethyl-2-phenyl-3-pyrazolone |
| Q27166457 |
| 4-hydroxyphenazone; nsc 174055 |
| CS-0020302 |
| BRD-K49759007-001-06-9 |
| CS-15446 |
| mfcd00003143 |
| C13501 |
| 4-hydroxy-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one |
| BAA67263 |
| antipyrine, 4-hydroxy- (6ci,7ci,8ci); 1,2-dihydro-4-hydroxy-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one; 4-hydroxy-1,5-dimethyl-3-oxo-2-phenyl pyrazoline; 4-hydroxyantipyrine; 4-hydroxyphenazone; nsc 174055 |
| HY-B2150 |
| EN300-9470206 |
| 4-hydroxy-1,5-dimethyl-2-phenyl-2,3-dihydro-1h-pyrazol-3-one |
| Excerpt | Reference | Relevance |
|---|---|---|
| "01) by verapamil (80 mg three times daily for 2 days prior to antipyrine administration and 2 days following) while half-life was increased from 13." | ( The effect of verapamil on antipyrine pharmacokinetics and metabolism in man. Bach, D; Blevins, R; Edwards, DJ; Kerner, N; Rubenfire, M, 1986) | 0.27 |
| " The first three months of life were characterised by a steady decrease in the apparent volume of distribution (aVd) and half-life (t0." | ( Effect of age on the pharmacokinetics of antipyrine in calves. Janus, K; Suszycka, J, 1996) | 0.29 |
| " The plasma elimination half-life of antipyrine was significantly elevated by 23% at 11 weeks postinfection (p." | ( Effect of experimental fasciolosis on antipyrine metabolism and clearance in water buffaloes. Bayón, JE; Ferre, I; González-Gallego, J; Jiang, SX; Mao, XZ, 2000) | 0.31 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Unknown additional peaks were detected in urine after NORA dosing but not after HMA or OHA administration." | ( The pharmacokinetics of antipyrine and three of its metabolites in the rabbit: intravenous administration of pure metabolites. Abul-Hajj, Y; Awni, WM; St Peter, JV, 1991) | 0.28 |
| " Mefloquine (750 mg) had no significant effect on salivary kinetics of antipyrine or on the metabolic clearance of antipyrine to its three main metabolites, 3-hydroxymethylantipyrine, 4-hydroxyantipyrine and norantipyrine, when antipyrine was administered either 2 h or 2 weeks after dosing with mefloquine." | ( The pharmacokinetics of mefloquine in man: lack of effect of mefloquine on antipyrine metabolism. Back, DJ; Breckenridge, AM; Howells, RE; Rivière, JH, 1985) | 0.46 |
| " When data before metronidazole dosing were compared with those after metronidazole dosing, there were no changes in total plasma clearance of diazepam (0." | ( Interaction between metronidazole and drugs eliminated by oxidative metabolism. Gugler, R; Jensen, JC, 1985) | 0.27 |
| Class | Description |
|---|---|
| ring assembly | Two or more cyclic systems (single rings or fused systems) which are directly joined to each other by double or single bonds are named ring assemblies when the number of such direct ring junctions is one less than the number of cyclic systems involved. |
| pyrazoles | |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| thioredoxin reductase | Rattus norvegicus (Norway rat) | Potency | 70.7946 | 0.1000 | 20.8793 | 79.4328 | AID588453 |
| 15-lipoxygenase, partial | Homo sapiens (human) | Potency | 12.5893 | 0.0126 | 10.6917 | 88.5700 | AID887 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 31.6228 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| USP1 protein, partial | Homo sapiens (human) | Potency | 35.4813 | 0.0316 | 37.5844 | 354.8130 | AID504865 |
| thioredoxin glutathione reductase | Schistosoma mansoni | Potency | 11.2202 | 0.1000 | 22.9075 | 100.0000 | AID485364 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 8.9125 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| bromodomain adjacent to zinc finger domain 2B | Homo sapiens (human) | Potency | 0.7079 | 0.7079 | 36.9043 | 89.1251 | AID504333 |
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 8.9125 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| geminin | Homo sapiens (human) | Potency | 3.6626 | 0.0046 | 11.3741 | 33.4983 | AID624296 |
| Polyunsaturated fatty acid lipoxygenase ALOX15B | Homo sapiens (human) | Potency | 10.0000 | 0.3162 | 12.7657 | 31.6228 | AID881 |
| Histamine H2 receptor | Cavia porcellus (domestic guinea pig) | Potency | 10.0000 | 0.0063 | 8.2350 | 39.8107 | AID881 |
| TAR DNA-binding protein 43 | Homo sapiens (human) | Potency | 35.4813 | 1.7783 | 16.2081 | 35.4813 | AID652104 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
| AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal of biomolecular screening, Jul, Volume: 21, Issue:6 | A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 32 (50.79) | 18.7374 |
| 1990's | 19 (30.16) | 18.2507 |
| 2000's | 4 (6.35) | 29.6817 |
| 2010's | 6 (9.52) | 24.3611 |
| 2020's | 2 (3.17) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (9.91) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 2 (3.03%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 64 (96.97%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||