Page last updated: 2024-12-09

2-(4-bromophenyl)-4-methyl-1H-pyrazol-5-one

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

2-(4-bromophenyl)-4-methyl-1H-pyrazol-5-one, also known as **4-bromoantipyrine**, is a synthetic organic compound belonging to the pyrazolone family.

Here's a breakdown of its characteristics and importance:

**Structure and Properties:**

* **Structure:** 4-bromoantipyrine has a pyrazolone ring system with a bromine atom attached to the phenyl ring at the para position and a methyl group attached at the 4-position.
* **Appearance:** It's a white to off-white crystalline powder.
* **Solubility:** Soluble in various organic solvents like ethanol, chloroform, and ether.
* **Melting Point:** Around 110-112°C.

**Research Importance:**

4-bromoantipyrine is important for research in several fields, primarily due to its:

* **Pharmacological Activity:**
* **Anti-inflammatory:** 4-bromoantipyrine exhibits significant anti-inflammatory activity, similar to other pyrazolone derivatives like antipyrine.
* **Analgesic:** It also possesses analgesic (pain-relieving) properties.
* **Antipyretic:** 4-bromoantipyrine can reduce fever.
* **Chemical Reactivity:**
* **Versatile Building Block:** It serves as a starting material for the synthesis of a wide range of pyrazolone derivatives with potentially diverse pharmacological actions.
* **Modification Potential:** The bromine atom on the phenyl ring can be easily modified through various chemical reactions, allowing the creation of new compounds with tailored properties.

**Research Applications:**

* **Drug Discovery:** 4-bromoantipyrine is used in the development of new drugs for inflammation, pain, and fever.
* **Chemical Synthesis:** Its reactivity and versatility make it a valuable building block for the synthesis of novel compounds with diverse biological activities.
* **Material Science:** 4-bromoantipyrine's properties have been investigated for potential applications in materials science, including optical materials and polymers.

**Note:** While 4-bromoantipyrine has shown promise in research, it's important to note that its use in human medicine might be limited due to potential side effects and the availability of safer alternatives.

If you're interested in learning more about specific research applications or the detailed pharmacological mechanisms of 4-bromoantipyrine, you can search for research articles on relevant databases like PubMed or Google Scholar.

Cross-References

ID SourceID
PubMed CID687960
CHEMBL ID1526365
CHEBI ID109755

Synonyms (21)

Synonym
REGID4263638
1-(4-bromophenyl)-4-methyl-1h-pyrazol-3-ol
MLS000099962
smr000081157
CHEMDIV2_002559
CHEBI:109755
AKOS003343372
HMS1376E07
2-(4-bromophenyl)-4-methyl-1h-pyrazol-5-one
HMS2506G23
STK663745
1-(4-bromophenyl)-4-methylpyrazol-3-ol
24835-01-6
1h-pyrazol-3-ol, 1-(4-bromophenyl)-4-methyl-
MASVYRJFLZAGNC-UHFFFAOYSA-N
CHEMBL1526365
Q27189039
mfcd03767431
1-(p-bromophenyl)--g-hydroxy-4-methylpyrazole
CCG-276546
LS-07261
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
pyrazoles
ring assemblyTwo 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.
[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 Targets (12)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency12.58930.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency12.58930.025120.237639.8107AID886
Chain A, CruzipainTrypanosoma cruziPotency31.62280.002014.677939.8107AID1476
LuciferasePhotinus pyralis (common eastern firefly)Potency23.93410.007215.758889.3584AID588342
BRCA1Homo sapiens (human)Potency25.11890.89137.722525.1189AID624202
ATAD5 protein, partialHomo sapiens (human)Potency18.35640.004110.890331.5287AID504466; AID504467
IDH1Homo sapiens (human)Potency19.95260.005210.865235.4813AID686970
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency25.11890.001815.663839.8107AID894
DNA polymerase betaHomo sapiens (human)Potency89.12510.022421.010289.1251AID485314
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency112.20200.050127.073689.1251AID588590
neuropeptide S receptor isoform AHomo sapiens (human)Potency12.58930.015812.3113615.5000AID1461
Guanine nucleotide-binding protein GHomo sapiens (human)Potency11.22021.995325.532750.1187AID624287
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. 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.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. 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.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. 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.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID652178Confirmed Agonists of Novel Allosteric Modulators of the M1 Muscarinic Receptor2013Molecules (Basel, Switzerland), Jan-08, Volume: 18, Issue:1
Benchmarking ligand-based virtual High-Throughput Screening with the PubChem database.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (16.67)29.6817
2010's4 (66.67)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.35

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.

MetricThis Compound (vs All)
Research Demand Index12.35 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.30 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]