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

Details

Stereochemistry ACHIRAL
Molecular Formula C11H13N3O.ClH
Molecular Weight 239.701
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMPYRONE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=UZSCVCWALGRUTR-UHFFFAOYSA-N
InChI=1S/C11H13N3O.ClH/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9;/h3-7H,12H2,1-2H3;1H

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

Molecular Formula ClH
Molecular Weight 36.461
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
Protease-catalysed coupling of N-protected amino acids and peptides with 4-aminoantipyrine.
2009-02
An enzyme-chromogenic surface plasmon resonance biosensor probe for hydrogen peroxide determination using a modified Trinder's reagent.
2008-11-15
Secular trends in cholesterol lipoproteins and triglycerides and prevalence of dyslipidemias in an urban Indian population.
2008-10-24
A novel method for measuring human lipoprotein lipase and hepatic lipase activities in postheparin plasma.
2008-07
[Effect of high-frequency electroacupuncture on lipid metabolism in obesity rats].
2008-06
[Effect of herbicide tralkoxydim and 2-acylcyclohexane-1,3-diones on peroxidase activity].
2008-05-22
Photodegradation study of three dipyrone metabolites in various water systems: identification and toxicity of their photodegradation products.
2008-05
Facile and sensitive determination of selenium (IV) in pharmaceutical formulations by flow injection spectrophotometry.
2008-05
Occurrence, fate and assessment of polar metamizole (dipyrone) residues in hospital and municipal wastewater.
2008-04
Erythrocyte aldose reductase activity and sorbitol levels in diabetic retinopathy.
2008-03-24
Discovery and characterization of a putrescine oxidase from Rhodococcus erythropolis NCIMB 11540.
2008-03
Chronic prehepatic portal hypertension in the rat: is it a type of metabolic inflammatory syndrome?
2008-02-13
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.
2008-01-01
[Analysis of three metabolite residues of dipyrone in bovine muscle and pork muscle using high performance liquid chromatography].
2007-11
Exercise and postprandial lipaemia: effects on peripheral vascular function, oxidative stress and gastrointestinal transit.
2007-10-31
Independent associations of fasting insulin, glucose, and glycated haemoglobin with stroke and coronary heart disease in older women.
2007-08
Changes in serum adenosine deaminase activity during normal pregnancy.
2007-08
Dipyrone elicits substantial inhibition of peripheral cyclooxygenases in humans: new insights into the pharmacology of an old analgesic.
2007-08
Effect of 4-aminoantipyrine on gastric compliance and liquid emptying in rats.
2007-07
Neutral genetic drift can alter promiscuous protein functions, potentially aiding functional evolution.
2007-06-28
Phage display identification of functional binding peptides against 4-acetamidophenol (Paracetamol): an exemplified approach to target low molecular weight organic molecules.
2007-06-22
Inhibition of cyclooxygenases by dipyrone.
2007-06
Improvement of activity and stability of chloroperoxidase by chemical modification.
2007-05-18
Microalbuminuria among Type 1 and Type 2 diabetic patients of African origin in Dar Es Salaam, Tanzania.
2007-01-15
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
Copper(II) complexes with ligands derived from 4-amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one: synthesis and biological activity.
2006-11-17
Synthesis and characterization of pseudo-affinity ligand for penicillin acylase purification.
2006-11-15
Mechanism of ascorbic acid interference in biochemical tests that use peroxide and peroxidase to generate chromophore.
2006-11
[Cooxidation of phenol and 4-aminoantipyrin, catalyzed by polymers and copolymers of horseradish root peroxidase and Penicillium funiculosum 46.1 glucose oxidase].
2006-10-07
New and simple plate test for screening relative transfructosylation activity of fungi.
2006-09
[Detection of phenol by means of 4-aminophenazone according to Emerson].
2006-09
[Monitoring of adipocyte responsiveness by in situ microdialysis in lipodystrophy tissue: adjustment of a glycerol quantification method in small samples].
2006-08-03
Recovery of peroxides in saliva during home bleaching--influence of smoking.
2006-07
Kinetic modelling of phenol co-oxidation using horseradish peroxidase.
2006-07
Structure-guided recombination creates an artificial family of cytochromes P450.
2006-05
Determination of cefadroxil by sequential injection with spectrophotometric detector.
2006-04
Validation of a new high-performance liquid chromatography assay for nizatidine.
2006-04
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
Enzymatic-spectrophotometric determination of sucrose in coffee beans.
2005-10-15
Synthesis, spectroscopic and physicochemical characterization and biological activity of Co(II) and Ni(II) coordination compounds with 4-aminoantipyrine thiosemicarbazone.
2005
Flow-injection spectrophotometric determination of salbutamol with 4-aminoantipyrine.
2004-12-15
Sequential injection spectrophotometric determination of phenylephrine hydrochloride in pharmaceutical preparations.
2004-06-17
An improved flow system for phenols determination exploiting multicommutation and long pathlength spectrophotometry.
2004-02-27
Peroxidase-like activity on organic hydroperoxides of ion-exchange resins modified with metal-porphine analogues and analytical application for determination of linoleate hydroperoxide.
2001-04-12
Application of oxidative coupling reactions for the estimation of ritodrine hydrochloride in bulk sample and dosage forms.
2001-01-26
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 Mon Mar 31 21:26:48 GMT 2025
Edited
by admin
on Mon Mar 31 21:26:48 GMT 2025
Record UNII
F7WGH82I6D
Record Status Validated (UNII)
Record Version
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Name Type Language
AMPYRONE HYDROCHLORIDE
Common Name English
NSC-1740
Preferred Name English
1,5-DIMETHYL-2-PHENYL-4-AMINOPYRAZOLONE HYDROCHLORIDE
Systematic Name English
4-AMINOANTIPYRINE HYDROCHLORIDE
Common Name English
Code System Code Type Description
FDA UNII
F7WGH82I6D
Created by admin on Mon Mar 31 21:26:48 GMT 2025 , Edited by admin on Mon Mar 31 21:26:48 GMT 2025
PRIMARY
CAS
22198-72-7
Created by admin on Mon Mar 31 21:26:48 GMT 2025 , Edited by admin on Mon Mar 31 21:26:48 GMT 2025
PRIMARY
NSC
1740
Created by admin on Mon Mar 31 21:26:48 GMT 2025 , Edited by admin on Mon Mar 31 21:26:48 GMT 2025
PRIMARY
ECHA (EC/EINECS)
244-832-4
Created by admin on Mon Mar 31 21:26:48 GMT 2025 , Edited by admin on Mon Mar 31 21:26:48 GMT 2025
PRIMARY
PUBCHEM
72639
Created by admin on Mon Mar 31 21:26:48 GMT 2025 , Edited by admin on Mon Mar 31 21:26:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID8066769
Created by admin on Mon Mar 31 21:26:48 GMT 2025 , Edited by admin on Mon Mar 31 21:26:48 GMT 2025
PRIMARY
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