Structure via PubChem · Public domain (PubChem)
ampyrone
Sign in to saveAlso known as 4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one, Solvapyrin-A, Solnapyrin-A, Metapirazone, Aminoazophene, Aminoazophenazone, Aminoantipyrine, Aminoantipyrin
Ampyrone is a metabolite of aminopyrine with analgesic, anti-inflammatory, and antipyretic properties. While the parent drug, aminopyrine, has been discouraged due to the risk of agranulocytosis, ampyrone itself has significantly lower toxicity. It is used as a reagent for biochemical reactions producing peroxides or phenols. Ampyrone stimulates liver microsomes and is also used to measure extracellular water.
In the Vinony graph
Within Vinony's link graph, ampyrone is referenced by 381 other articles, and connects out to medication, aminophenazone and fenamic acid.
It sits within the topics Antipyretics, ECHA InfoCard ID from Wikidata and Human drug metabolites.
Its subject is documented across 13 Wikipedia language editions.
Chemical data
- Formula
- C11H13N3O
- Molecular weight
- 203.24 g/mol
- IUPAC name
- 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one
- SMILES
- CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N
- InChIKey
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N
- XLogP
- 0.1
- Polar surface area
- 49.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
262 papers- Ampyrone appended 1,2,3-triazole as selective fluorescent Cu(II) ion sensor: DFT and docking findings.Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy · 2023
- Ampyrone (4-Aminoantipyrine) is a Direct Agonist of Human Tyrosinase and Potential Therapeutic for Oculocutaneous Albinism and Disorders of Hypopigmentation.bioRxiv : the preprint server for biology · 2025
- Identification of Potential Therapeutic Targets for Sensorineural Hearing Loss and Evaluation of Drug Development Potential Using Mendelian Randomization Analysis.Bioengineering (Basel, Switzerland) · 2025
- Unnatural Amino Acid: 4-Aminopyrazolonyl Amino Acid Comprising Tri-Peptides Forms Organogel With Co-Solvent (EtOAc:Hexane).Frontiers in chemistry · 2022
- GABA enzymatic assay kit.Bioscience, biotechnology, and biochemistry · 2020
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 203.106
Show 4 more facts
- melting point
- 108
- chemical formula
- C₁₁H₁₃N₃O
- subject has role
- non-steroidal anti-inflammatory drug
- canonical SMILES
- CC1=C(C(=O)N(N1C)C2=CC=CC=C2)N
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Ampyrone is a metabolite of aminopyrine with analgesic, anti-inflammatory, and antipyretic properties. While the parent drug, aminopyrine, has been discouraged due to the risk of agranulocytosis, ampyrone itself has significantly lower toxicity. It is used as a reagent for biochemical reactions producing peroxides or phenols. Ampyrone stimulates liver microsomes and is also used to measure extracellular water.
By applying an ampyrone solution, scientists can make skin temporarily transparent (to red light); and e.g. see directly into the brain (of living young mice, when the skull is very thin, thus transparent, the solution doesn't have such an effect on it): "This opens a literal window to peek into the brain's development .. Not only can we image the structures of these neurons, but we can also image the neural activity over time in an animal model. In the future, this approach could enable us to look at how these circuits form during the development of an animal."
Excerpted from Wikipedia’s “ampyrone” article, available under the CC BY-SA 4.0 licence.