U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C11H13N3O
Molecular Weight 203.2404
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMPYRONE

SMILES

CN1N(C(=O)C(N)=C1C)C2=CC=CC=C2

InChI

InChIKey=RLFWWDJHLFCNIJ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C11H13N3O
Molecular Weight 203.2404
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Ampyrone (4-Aminoantipyrine or AAP) is a metabolite of aminophenazone and is an aromatic substance with analgesic, antipyretic and anti-inflammatory properties. When combined with the antineoplastic agents, ampyrone decreased their genotoxic, mutagenic, apoptotic, and phagocytic effects. However, ampyrone usually produces side effects, such as the risk of agranulocytosis. Although ampyrone is scarcely ever administered as an analgesic because of the potential side effects, as a raw material, it is mostly used to produce ampyrone derivatives, which have better biological activities. In addition, it is used as a reagent for biochemical reactions producing peroxides or phenols and can also be used to detect phenols in the environment. Exposure to ampyrone could induce changes in the enzyme catalase structure and function.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rat. Human data not available.

Originator

Sources: DOI: 10.1002/hlca.19250080123

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P04178
Gene ID: 397036.0
Gene Symbol: SOD1
Target Organism: Sus scrofa (Pig)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Peroxidase-like activity on organic hydroperoxides of ion-exchange resins modified with metal-porphine analogues and analytical application for determination of linoleate hydroperoxide.
2001 Apr 12
Application of oxidative coupling reactions for the estimation of ritodrine hydrochloride in bulk sample and dosage forms.
2001 Jan 26
Flow-injection spectrophotometric determination of salbutamol with 4-aminoantipyrine.
2004 Dec 15
An improved flow system for phenols determination exploiting multicommutation and long pathlength spectrophotometry.
2004 Feb 27
Sequential injection spectrophotometric determination of phenylephrine hydrochloride in pharmaceutical preparations.
2004 Jun 17
Synthesis, spectroscopic and physicochemical characterization and biological activity of Co(II) and Ni(II) coordination compounds with 4-aminoantipyrine thiosemicarbazone.
2005
Enzymatic-spectrophotometric determination of sucrose in coffee beans.
2005 Oct 15
Synthesis, Spectral, and Biological Properties of Copper(II) Complexes of Thiosemicarbazones of Schiff Bases Derived from 4-Aminoantipyrine and Aromatic Aldehydes.
2006
Synthesis, Biological, Spectral, and Thermal Investigations of Cobalt(II) and Nickel(II) Complexes of N-Isonicotinamido -2',4'-Dichlorobenzalaldimine.
2006
A peroxidase-coupled continuous absorbance plate-reader assay for flavin monoamine oxidases, copper-containing amine oxidases and related enzymes.
2006
Synthesis and antitumor activity of some novel quinazoline derivatives bearing the biologically active thione moiety.
2006
Activation of transforming growth factor-beta1 and early atherosclerosis in systemic lupus erythematosus.
2006
Determination of cefadroxil by sequential injection with spectrophotometric detector.
2006 Apr
Validation of a new high-performance liquid chromatography assay for nizatidine.
2006 Apr
Recovery of peroxides in saliva during home bleaching--influence of smoking.
2006 Jul
Kinetic modelling of phenol co-oxidation using horseradish peroxidase.
2006 Jul
[Cooxidation of phenol and 4-aminoantipyrin, catalyzed by polymers and copolymers of horseradish root peroxidase and Penicillium funiculosum 46.1 glucose oxidase].
2006 Jul-Aug
Structure-guided recombination creates an artificial family of cytochromes P450.
2006 May
[Monitoring of adipocyte responsiveness by in situ microdialysis in lipodystrophy tissue: adjustment of a glycerol quantification method in small samples].
2006 May-Jun
Mechanism of ascorbic acid interference in biochemical tests that use peroxide and peroxidase to generate chromophore.
2006 Nov
Synthesis and characterization of pseudo-affinity ligand for penicillin acylase purification.
2006 Nov 15
Copper(II) complexes with ligands derived from 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: synthesis and biological activity.
2006 Nov 17
New and simple plate test for screening relative transfructosylation activity of fungi.
2006 Sep
[Detection of phenol by means of 4-aminophenazone according to Emerson].
2006 Sep
Synthesis, spectroscopic, and antimicrobial studies on bivalent nickel and copper complexes of bis(thiosemicrbazone).
2007
Spectroscopic, thermal and biological studies on some trivalent ruthenium and rhodium NS chelating thiosemicarbazone complexes.
2007
Independent associations of fasting insulin, glucose, and glycated haemoglobin with stroke and coronary heart disease in older women.
2007 Aug
Changes in serum adenosine deaminase activity during normal pregnancy.
2007 Aug
Dipyrone elicits substantial inhibition of peripheral cyclooxygenases in humans: new insights into the pharmacology of an old analgesic.
2007 Aug
Microalbuminuria among Type 1 and Type 2 diabetic patients of African origin in Dar Es Salaam, Tanzania.
2007 Jan 15
Effect of 4-aminoantipyrine on gastric compliance and liquid emptying in rats.
2007 Jul
Inhibition of cyclooxygenases by dipyrone.
2007 Jun
Phage display identification of functional binding peptides against 4-acetamidophenol (Paracetamol): an exemplified approach to target low molecular weight organic molecules.
2007 Jun 22
Neutral genetic drift can alter promiscuous protein functions, potentially aiding functional evolution.
2007 Jun 28
Improvement of activity and stability of chloroperoxidase by chemical modification.
2007 May 18
[Analysis of three metabolite residues of dipyrone in bovine muscle and pork muscle using high performance liquid chromatography].
2007 Nov
Exercise and postprandial lipaemia: effects on peripheral vascular function, oxidative stress and gastrointestinal transit.
2007 Oct 31
Occurrence, fate and assessment of polar metamizole (dipyrone) residues in hospital and municipal wastewater.
2008 Apr
Chronic prehepatic portal hypertension in the rat: is it a type of metabolic inflammatory syndrome?
2008 Feb 13
Implication of a mutation in the flavin binding site on the specific activity and substrate specificity of glycine oxidase from Bacillus subtilis produced by directed evolution.
2008 Jan 1
[Effect of herbicide tralkoxydim and 2-acylcyclohexane-1,3-diones on peroxidase activity].
2008 Jan-Feb
A novel method for measuring human lipoprotein lipase and hepatic lipase activities in postheparin plasma.
2008 Jul
[Effect of high-frequency electroacupuncture on lipid metabolism in obesity rats].
2008 Jun
Discovery and characterization of a putrescine oxidase from Rhodococcus erythropolis NCIMB 11540.
2008 Mar
Erythrocyte aldose reductase activity and sorbitol levels in diabetic retinopathy.
2008 Mar 24
Photodegradation study of three dipyrone metabolites in various water systems: identification and toxicity of their photodegradation products.
2008 May
Facile and sensitive determination of selenium (IV) in pharmaceutical formulations by flow injection spectrophotometry.
2008 May
An enzyme-chromogenic surface plasmon resonance biosensor probe for hydrogen peroxide determination using a modified Trinder's reagent.
2008 Nov 15
Secular trends in cholesterol lipoproteins and triglycerides and prevalence of dyslipidemias in an urban Indian population.
2008 Oct 24
Protease-catalysed coupling of N-protected amino acids and peptides with 4-aminoantipyrine.
2009 Feb
Patents

Sample Use Guides

Rat: 60-360 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:38 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:38 UTC 2023
Record UNII
0M0B7474RA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMPYRONE
Common Name English
4-AMINOPHENAZONE
Systematic Name English
4-AMINO-1,5-DIMETHYL-2-PHENYL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE
Systematic Name English
SOLVAPYRIN A
Common Name English
METAPIRAZONE
Common Name English
NSC-60242
Code English
4-AMINOANTIPYRINE [MI]
Common Name English
AA METABOLITE OF METAMIZOLE
Common Name English
4-AMINOANTIPYRINE
MI  
Common Name English
AMINOANTIPYRINE
Common Name English
METAMIZOLE SODIUM MONOHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
4-AMINO-1,5-DIMETHYL-2-PHENYL-PYRAZOL-3-ONE
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
201-452-3
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
NSC
60242
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
CHEBI
59026
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID8048860
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
MESH
D000675
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
MERCK INDEX
m1683
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY Merck Index
CAS
83-07-8
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
PUBCHEM
2151
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
WIKIPEDIA
AMPYRONE
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
FDA UNII
0M0B7474RA
Created by admin on Fri Dec 15 14:58:38 UTC 2023 , Edited by admin on Fri Dec 15 14:58:38 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP