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Product Description
Mechanism of action
Aminophenazone (aminopyrine) is a pyrazolone derivative with analgesic, antipyretic and anti-inflammatory properties. It inhibits cyclo‑oxygenase (COX) enzymes, reducing prostaglandin synthesis in the hypothalamus and peripheral tissues. Of scientific significance is its hepatic metabolism: aminophenazone undergoes N‑demethylation via CYP2C9 and CYP3A4 to form labelled CO₂ in tracer studies. This property underpins the aminopyrine breath test, a sensitive clinical research method for evaluating functional hepatic microsomal activity.
Benefits and advantages
Although discontinued as a therapeutic agent due to toxicity, aminophenazone remains indispensable in metabolic research. It serves as a probe for hepatic oxidative capacity, CYP induction studies, and characterisation of xenobiotic biotransformation. Its predictable pharmacokinetics allow controlled quantitative analysis of liver enzyme function.
Side effects and risks
Serious adverse reactions historically included agranulocytosis, hepatocellular injury, hypersensitivity reactions and shock. These toxicities arise partly from reactive metabolites formed during hepatic oxidation. Strict protective handling conditions are mandatory to avoid exposure.
Datasheet
| Molecular Formula | C13H17N3O |
|---|---|
| Molecular Weight | 231.29 g/mol |
| CAS Number | 58-15-1 |
| Storage Condition | …MATERIALS WHICH…CAN DECOMP INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT…STORED IN COOL, WELL-VENTILATED PLACE, OUT OF…RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD…PERIODICALLY INSPECTED & MONITORED. INCOMPATIBLE MATERIALS…ISOLATED FROM EACH OTHER. |
| Solubility | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992) |
| Purity | Purity information is available upon request (COA). |
| Synonym | aminophenazone; AMINOPYRINE; Amidopyrine; 58-15-1; 4-Dimethylaminoantipyrine |
| IUPAC/Chemical Name | 4-(dimethylamino)-1,5-dimethyl-2-phenylpyrazol-3-one |
| InChl Key | RMMXTBMQSGEXHJ-UHFFFAOYSA-N |
| InChl Code | InChI=1S/C13H17N3O/c1-10-12(14(2)3)13(17)16(15(10)4)11-8-6-5-7-9-11/h5-9H,1-4H3 |
| References |
3D Conformer.
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