CHEBI:59026 - 4-aminoantipyrine

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ChEBI Name 4-aminoantipyrine
ChEBI ID CHEBI:59026
Definition A pyrazolone, a member of the class of pyrazoles that is antipyrine substituted at C-4 by an amino group. It is a metabolite of aminopyrine and of metamizole.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C11H13N3O
Net Charge 0
Average Mass 203.24040
Monoisotopic Mass 203.106
InChI InChI=1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3
InChIKey RLFWWDJHLFCNIJ-UHFFFAOYSA-N
SMILES Cc1c(N)c(=O)n(-c2ccccc2)n1C
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): drug metabolite

EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
marine xenobiotic metabolite
Any metabolite produced by metabolism of a xenobiotic compound in marine macro- and microorganisms.
Application(s): antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antirheumatic drug
A drug used to treat rheumatoid arthritis.
peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4-aminoantipyrine (CHEBI:59026) has functional parent antipyrine (CHEBI:31225)
4-aminoantipyrine (CHEBI:59026) has role antipyretic (CHEBI:35493)
4-aminoantipyrine (CHEBI:59026) has role antirheumatic drug (CHEBI:35842)
4-aminoantipyrine (CHEBI:59026) has role drug metabolite (CHEBI:49103)
4-aminoantipyrine (CHEBI:59026) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
4-aminoantipyrine (CHEBI:59026) has role marine xenobiotic metabolite (CHEBI:83399)
4-aminoantipyrine (CHEBI:59026) has role non-narcotic analgesic (CHEBI:35481)
4-aminoantipyrine (CHEBI:59026) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
4-aminoantipyrine (CHEBI:59026) has role peripheral nervous system drug (CHEBI:49110)
4-aminoantipyrine (CHEBI:59026) is a primary amino compound (CHEBI:50994)
4-aminoantipyrine (CHEBI:59026) is a pyrazolone (CHEBI:83328)
IUPAC Name
4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
Synonyms Sources
4-AAP ChemIDplus
4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one ChemIDplus
4-Aminoantipyrene ChemIDplus
4-Aminophenazone ChemIDplus
Aminoantipyrin ChemIDplus
Aminoantipyrine ChemIDplus
Aminoazophenazone ChemIDplus
Aminoazophene ChemIDplus
Ampyrone ChemIDplus
Metapirazone ChemIDplus
Solnapyrin-A ChemIDplus
Solvapyrin-A ChemIDplus
Manual Xrefs Databases
Ampyrone Wikipedia
LSM-5369 LINCS
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Registry Numbers Types Sources
181635 Beilstein Registry Number Beilstein
181635 Reaxys Registry Number Reaxys
83-07-8 CAS Registry Number NIST Chemistry WebBook
83-07-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
24056243 PubMed citation Europe PMC
24508878 PubMed citation Europe PMC
25476354 PubMed citation Europe PMC
25652276 PubMed citation Europe PMC
25947243 PubMed citation Europe PMC
3425858 PubMed citation Europe PMC
Last Modified
25 February 2016
General Comments
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
2014-10-29 Metabolite of Aminopyrine/Metamizol